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Product Details
European Community (EC) Number | 694-843-7 |
Uses |
(R)-2-(methoxycarbonylamino)-2-phenylacetic acid is used as a chiral building block in organic synthesis and in the preparation of various pharmaceuticals. |
IUPAC Name: (2R)-2-(methoxycarbonylamino)-2-phenylacetic acid
Isomeric SMILES: COC(=O)N[C@H](C1=CC=CC=C1)C(=O)O
InChIKey: GOJLQSAREKTKPT-MRVPVSSYSA-N
InChI: InChI=1S/C10H11NO4/c1-15-10(14)11-8(9(12)13)7-5-3-2-4-6-7/h2-6,8H,1H3,(H,11,14)(H,12,13)/t8-/m1/s1
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This article describes the synthesis of (R)-2-(methoxycarbonylamino)-2-phenylacetic acid using an asymmetric reduction method with borane-dimethyl sulfide. The compound is an important chiral building block in organic synthesis and pharmaceutical development.
(R)-phenylglycine
methyl chloroformate
(2R)-2-[(methoxycarbonyl)amino]-2-phenylacetic acid
Conditions | Yield |
---|---|
With sodium hydroxide; In water; at 0 ℃; for 1.5h;
|
92% |
With sodium hydroxide; In water; at 0 ℃; for 1.33333h;
|
91% |
(R)-phenylglycine; methyl chloroformate; With sodium hydroxide; In water; at 0 ℃; for 1h;
With hydrogenchloride; In water;
|
91% |
With sodium hydroxide; In water; at 0 ℃; for 1h;
|
91% |
With sodium hydroxide; In water; at 0 ℃; for 1h;
|
91% |
(R)-phenylglycine; methyl chloroformate; With sodium hydroxide; In water; at 0 - 20 ℃; for 1.33h;
With hydrogenchloride; In water;
|
91% |
With sodium hydroxide; In water; at 0 ℃; for 1.33333h;
|
91% |
With sodium hydroxide; In water; at 0 ℃; for 1.33333h;
|
91% |
With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃;
|
80% |
(R)-phenylglycine; With sodium hydroxide; In water; at 0 ℃; for 0.0833333h;
methyl chloroformate; In 1,4-dioxane; water; at 25 - 30 ℃; for 24h;
|
71% |
With sodium carbonate; sodium hydroxide; In water; at 20 ℃; for 3.25h; Cooling with ice;
|
67% |
With sodium carbonate; sodium hydroxide; In water; at 20 ℃; for 3.25h; Cooling with ice;
|
67% |
With sodium carbonate; sodium hydroxide; In water; at 20 ℃; for 3.25h; Cooling with ice;
|
67% |
With sodium carbonate; sodium hydroxide; In water; at 20 ℃; for 3.25h; Cooling with ice;
|
67% |
With sodium carbonate; sodium hydroxide; In water; at 20 ℃; for 3.25h; Cooling with ice;
|
67% |
With sodium carbonate; sodium hydroxide; In water; at 20 ℃; for 3.25h; Cooling with ice;
|
63% |
With sodium hydroxide; In water; toluene; at 20 ℃; for 12h; Cooling with ice;
|
62% |
(R)-phenylglycine; methyl chloroformate; With sodium hydroxide; In water; at 0 ℃; for 1.33333h;
With hydrogenchloride; In water;
|
|
(R)-phenylglycine; methyl chloroformate; With sodium hydroxide; In water; at 0 ℃;
With hydrogenchloride; In water;
|
|
(R)-phenylglycine; With lithium hydroxide; In water; at 0 ℃;
methyl chloroformate; In water; at 0 ℃; for 2h;
|
|
(R)-phenylglycine; methyl chloroformate; With sodium hydroxide; In water; at 0 ℃; for 1.33333h;
With hydrogenchloride; In diethyl ether; water; at 0 ℃;
|
|
(R)-phenylglycine; methyl chloroformate; With sodium hydroxide; In water; at 0 ℃; for 1.33333h;
With hydrogenchloride; In water;
|
|
(R)-phenylglycine; methyl chloroformate; With sodium hydroxide; In water; at 0 ℃; for 1.33333h;
With hydrogenchloride; In diethyl ether; water; at 0 ℃;
|
|
With LiOH; In water;
|
|
With sodium hydroxide; In water; at 0 ℃; for 1.33333h;
|
|
With sodium hydroxide; In 1,4-dioxane; water; at 0 - 20 ℃;
|
|
With sodium hydroxide; In 1,4-dioxane; at 0 - 20 ℃;
|
(R)-tert-butyl 2-(methoxycarbonylamino)-2-phenylacetate
(2R)-2-[(methoxycarbonyl)amino]-2-phenylacetic acid
Conditions | Yield |
---|---|
With trifluoroacetic acid; In dichloromethane; for 22.1h; Cooling with ice/water;
|
|
With trifluoroacetic acid; In dichloromethane; for 22h;
|
|
With trifluoroacetic acid; In dichloromethane; Cooling with ice;
|
|
With trifluoroacetic acid; In dichloromethane; Cooling with ice;
|
|
With trifluoroacetic acid; In dichloromethane; for 22h; Cooling with ice;
|
|
With trifluoroacetic acid; In dichloromethane; for 20h; Cooling with ice;
|
|
With trifluoroacetic acid; In dichloromethane; for 22.14h; Cooling with ice/water;
|
|
With trifluoroacetic acid; In dichloromethane; for 22h; Cooling with ice;
|
|
With trifluoroacetic acid; In dichloromethane; for 22h; Cooling with ice;
|
|
With trifluoroacetic acid; In dichloromethane; for 22.11h; Cooling with ice;
|
|
With trifluoroacetic acid; In dichloromethane; for 22h; Cooling with ice;
|
5.57 g |
With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 22.1167h;
|
|
With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 22h;
|
|
With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 22.1167h;
|
|
With trifluoroacetic acid; In dichloromethane; for 22.1167h; Cooling with ice/water;
|
|
With trifluoroacetic acid; In dichloromethane; Cooling with ice-water bath;
|
|
With trifluoroacetic acid; In dichloromethane; Cooling with ice;
|
(R)-tert-butyl 2-(methoxycarbonylamino)-2-phenylacetate
methyl N-benzylcarbamate
N-Benzyl-N-trimethylsilyl-carbamidsaeure-methylester
benzylamine
dimethyl (4,4'-biphenyldiylbis(1H-imidazole-5,2-diyl(1S)-1,1-ethanediyl(methylimino)((1R)-2-oxo-1-phenyl-2,1-ethanediyl)))biscarbamate
methyl ((1R)-2-((2S)-2-(5-(4'-(2-((1S)-1-(((2R)-2-((methoxy-carbonyl)amino)-2-phenyl-acetyl)(methyl)amino)ethyl)-1H-imidazol-5-yl)-4-biphenylyl)-1H-imidazol-2-yl)-1-pyrrolidinyl)-2-oxo-1-phenyl-ethyl)carbamate
C48H46N8O6
C46H48N8O6
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