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Product Details
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Chemical Properties |
Brown Oil |
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Uses |
Methyl (S)-Pyroglutamate (cas# 4931-66-2) is a compound useful in organic synthesis. L-Pyroglutamic Acid Methyl Ester is used as a building block in organic synthesis and in the preparation of various pharmaceuticals. |
IUPAC Name: methyl (2S)-5-oxopyrrolidine-2-carboxylate
Isomeric SMILES: COC(=O)[C@@H]1CCC(=O)N1
InChIKey: HQGPKMSGXAUKHT-BYPYZUCNSA-N
InChI: InChI=1S/C6H9NO3/c1-10-6(9)4-2-3-5(8)7-4/h4H,2-3H2,1H3,(H,7,8)/t4-/m0/s1
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They were formulated into a 40% solution of propylene glycol with increasing concentrations ofN-methyl-2-pyrrolidone (NMP) (0.0 to 20.0%), dodecylazacycloheptan-2-one (laurocapram) and a new compound dodecyl-L-pyroglutamate (DLP; 0.0 to 0.5%). The lag time was twice as long in this case in comparison with the formulations containing NMP.
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methanol
L-Pyroglutamic acid
methyl (S)-pyroglutamate
| Conditions | Yield |
|---|---|
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With thionyl chloride; at 0 - 25 ℃;
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100% |
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With methanesulfonic acid; In chloroform; water; Reflux;
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100% |
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With Dowex-50W (X8-200) resin; Inert atmosphere; Reflux;
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100% |
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With thionyl chloride; for 0.5h; Heating;
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99.3% |
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With Amberlyst 15 resin; for 24h; Heating;
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99% |
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With Dowex ion-exchange resin;
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98% |
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With Dowex 50 W X 8; for 4h; Heating;
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97% |
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With Amberlyst 15 wet resin; for 24h; Reflux;
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97% |
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With Dowex; for 16h; Heating;
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96% |
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With Dowex 50W X 8; Heating;
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95% |
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With thionyl chloride; at 20 ℃; for 48h;
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95% |
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With thionyl chloride; Ambient temperature;
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94% |
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With thionyl chloride; at -5 - 20 ℃; for 10h;
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94% |
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With thionyl chloride; at 20 ℃; for 12h;
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94% |
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With thionyl chloride; for 3h; Ambient temperature;
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93% |
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With Amberlyst 15; Reflux;
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93% |
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With thionyl chloride;
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92% |
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With thionyl chloride; at 0 - 20 ℃; Inert atmosphere;
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92% |
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With thionyl chloride; at 20 ℃; for 24h;
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92% |
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With thionyl chloride; In N,N-dimethyl-formamide; for 26h; Ambient temperature;
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91% |
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With thionyl chloride; N,N-dimethyl-formamide; for 24h; Ambient temperature;
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91% |
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With thionyl chloride;
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91% |
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With toluene-4-sulfonic acid; for 12h; Heating;
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90% |
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With thionyl chloride; at 0 - 20 ℃; for 4h; Inert atmosphere; Schlenk technique;
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90% |
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With thionyl chloride; at 0 - 20 ℃; for 3h;
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90% |
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With thionyl chloride; for 1.5h; Ambient temperature;
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89.1% |
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With thionyl chloride; at 20 ℃; for 24h;
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85% |
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With thionyl chloride; In toluene; at -15 - 20 ℃; Inert atmosphere;
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83% |
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With thionyl chloride; for 72h;
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81% |
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With thionyl chloride; at -15 - 20 ℃; Inert atmosphere;
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81% |
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With thionyl chloride; at 20 ℃; for 16h; Inert atmosphere;
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81% |
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With thionyl chloride; at -18 - 20 ℃;
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81% |
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With thionyl chloride; for 2h; Ambient temperature;
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80% |
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With thionyl chloride; for 24h; Ambient temperature;
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80% |
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With thionyl chloride; at 20 ℃; for 3h; pH=0;
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80% |
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With thionyl chloride; at 20 ℃;
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80% |
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With thionyl chloride; at 20 ℃; for 14h;
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79% |
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With thionyl chloride; for 1.5h; Heating;
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76% |
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With thionyl chloride; at 20 ℃; Cooling with ice;
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72% |
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With thionyl chloride; at 20 ℃; for 2h;
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70% |
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With thionyl chloride; at 0 - 20 ℃;
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70% |
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With thionyl chloride; at 0 - 20 ℃;
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70% |
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With thionyl chloride; at 0 ℃; for 0.5h;
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67% |
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With thionyl chloride; at 0 - 20 ℃; for 3h;
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67.6% |
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With thionyl chloride; at 0 - 20 ℃; for 3h; Inert atmosphere; Sealed tube;
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67.6% |
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With thionyl chloride; at 0 - 20 ℃; for 3h;
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67.6% |
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With thionyl chloride; at 0 - 20 ℃; for 3h;
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67.6% |
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With thionyl chloride; at 0 - 20 ℃; for 3h;
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67.6% |
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With thionyl chloride; at 0 - 20 ℃; for 3h;
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67.6% |
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With thionyl chloride; at 0 - 20 ℃; for 3h;
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67.6% |
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With thionyl chloride; at 0 - 20 ℃; for 3h;
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67.6% |
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With thionyl chloride; at 0 - 40 ℃;
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58% |
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sulfuric acid; In benzene; Heating;
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sulfuric acid; In benzene; for 20h; Heating;
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With thionyl chloride;
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With thionyl chloride; for 2h; Ambient temperature;
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With Dowex 50WX2-200; for 3h; Heating;
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With thionyl chloride; at 20 ℃; for 48h;
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27.70 g |
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With thionyl chloride; at -20 - 20 ℃;
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With thionyl chloride; at -15 - 20 ℃;
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With thionyl chloride; at 0 - 20 ℃;
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With thionyl chloride; at -15 ℃; for 2h;
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|
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With thionyl chloride; at -15 - 20 ℃; for 2.5h;
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With hydrogenchloride; at 20 ℃; for 21h;
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With thionyl chloride; at 10 - 30 ℃; for 2.08333h;
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With thionyl chloride; at 10 - 30 ℃; for 2.08333h;
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With thionyl chloride; at 0 - 23 ℃; for 12h;
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With Dowex-H+; Heating / reflux;
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With thionyl chloride;
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With thionyl chloride; at -15 - 20 ℃;
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With thionyl chloride; at 20 ℃;
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With thionyl chloride; In methanol; at 0 - 20 ℃; for 2h;
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With hydrogenchloride; In water; at 20 ℃; for 24h;
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With toluene-4-sulfonic acid; for 24h; Reflux;
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With dmap; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;
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With thionyl chloride; at -5 - 30 ℃;
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With thionyl chloride; at 20 ℃; Cooling with ice; Inert atmosphere;
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With thionyl chloride; at 20 ℃; for 1h;
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With thionyl chloride;
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With thionyl chloride; at 0 - 18 ℃; for 1h;
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With toluene-4-sulfonic acid; for 30h; Reflux;
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3.161 g |
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With thionyl chloride; at 20 ℃; for 1h; Inert atmosphere;
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L-Pyroglutamic acid
methyl (S)-pyroglutamate
| Conditions | Yield |
|---|---|
|
With sulfuryl dichloride; sodium carbonate; In methanol; ethyl acetate;
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92.8% |
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With sulfuryl dichloride; sodium carbonate; In methanol; ethyl acetate;
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92.8% |
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With sulfuryl dichloride; sodium carbonate; In methanol; water; ethyl acetate; N,N-dimethyl-formamide;
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91% |
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With sulfuryl dichloride; sodium carbonate; In methanol; water; ethyl acetate; N,N-dimethyl-formamide;
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91% |
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Multi-step reaction with 2 steps
1: SOCl2
With thionyl chloride;
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Multi-step reaction with 3 steps
1: 100 percent / saccharin / 2.5 h / Heating
2: 100 percent Chromat. / oxalyl chloride / CH2Cl2 / Heating
3: 86 percent / CH2Cl2 / 0.08 h / Heating
With oxalyl dichloride; saccharin; In dichloromethane;
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With thionyl chloride; potassium carbonate; In methanol; water; ethyl acetate;
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With thionyl chloride; In methanol; at 0 - 20 ℃; for 3.5h;
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methanol
D-Glutamic acid
pyroglutamoyl chloride
dimethyl N-benzylideneglutamate
methyl N-formylpyroglutamate
Pyroglutamic acid
N-methoxy methyl pyroglutamate de methyle
methyl methylene bis-pyroglutamate
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