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74844-91-0

  • Product NameN-BOC-L-Hydroxyproline methyl ester
  • Molecular FormulaC11H19NO5
  • Molecular Weight245.276
  • Purity99%
  • AppearanceClear colourless oil
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Product Details

Quick Details

  • CasNo： 74844-91-0
  • Molecular Formula： C11H19NO5
  • Appearance： Clear colourless oil
  • Purity： 99%

Pharmaceutical Intermediates N-BOC-L-Hydroxyproline methyl Ester 74844-91-0 Crystalline Powder

  • Molecular Formula:C11H19NO5
  • Molecular Weight:245.276
  • Appearance/Colour:Clear colourless oil 
  • Vapor Pressure:0mmHg at 25°C 
  • Melting Point:91-96 °C 
  • Refractive Index:1.501 
  • Boiling Point:335.244 °C at 760 mmHg 
  • PKA:14.27±0.40(Predicted) 
  • Flash Point:156.55 °C 
  • PSA：76.07000 
  • Density:1.217 g/cm3 
  • LogP:0.46760 

N-Boc-trans-4-Hydroxy-L-proline methyl ester(Cas 74844-91-0) Usage

Chemical Properties

Clear Colourless Oil

Uses

N-BOC-L-Hydroxyproline methyl ester is A potential iNOS inhibitor.It is used in the synthesis of For-Met-Leu-Phe-OMe (fMLF-OMe) analogues based on Met residue replacement by 4-amino-proline scaffold.

Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)O  
InChIKey: MZMNEDXVUJLQAF-SFYZADRCSA-N  
InChI: InChI=1S/C11H19NO5/c1-11(2,3)17-10(15)12-6-7(13)5-8(12)9(14)16-4/h7-8,13H,5-6H2,1-4H3/t7-,8+/m1/s1  

74844-91-0 Relevant articles

Novel sulfur and selenium containing bis-α-amino acids from 4-hydroxyproline

Romualdo Caputo, Marina DellaGreca, Ivan de Paola, Domenico Mastroianni & Luigi Longobardo

Amino Acids volume 38, pages305–310 (2010)

At this stage, the addition of either the cis iodide 8 or the trans tosylate 9 (Scheme 4), prepared as described above from N-Boc-l-hydroxyproline methyl ester, followed by slow cooling of …

Synthesis of Ribo-Azanucleosides by Anodic Oxidation: Reactivity Control of Intermediate for Efficient Access to Pharmacophores

Okamoto, Kazuhiro,Shoji, Takao,Tsutsui, Mizuki,Shida, Naoki,Chiba, Kazuhiro

, p. 17902 - 17905 (2018)

Azanucleosides, the sugar-modified nucle...

74844-91-0 Process route

di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

cis-L-hydroxyproline methyl ester
81102-38-7,775275-31-5,790644-51-8,754962-86-2

cis-L-hydroxyproline methyl ester

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester
74844-91-0,114676-69-6,135042-17-0,227935-38-8,102195-79-9

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester

Conditions
Conditions Yield
With sodium hydrogencarbonate; In methanol; at 20 ℃; Inert atmosphere;
90%
With triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 16.5h;
65%
With triethylamine; In dichloromethane; Yield given; Ambient temperature;
 
With triethylamine;
 
With sodium hydrogencarbonate; In chloroform; water; at 20 ℃; for 2h;
 
Boc-(2S,4S)-p-nitrobenzoate-4-hydroxyproline methyl ester
168264-25-3

Boc-(2S,4S)-p-nitrobenzoate-4-hydroxyproline methyl ester

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester
74844-91-0,114676-69-6,135042-17-0,227935-38-8,102195-79-9

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester

Conditions
Conditions Yield
With sodium methylate; In methanol;
95%
With methanol; sodium azide; at 40 ℃; for 4h;
85%
With sodium azide; In methanol; at 40 ℃; for 40h; Inert atmosphere;
73%
With sodium azide; In acetone; for 14h; Reflux;
65%
Boc-(2S,4S)-p-nitrobenzoate-4-hydroxyproline methyl ester; With sodium azide; In acetone; for 14h; Reflux;
With water; In ethyl acetate;
65%
Boc-(2S,4S)-p-nitrobenzoate-4-hydroxyproline methyl ester; With methanol; potassium hydroxide; at 0 ℃; for 0.5h; Cooling with ice bath; Inert atmosphere;
With hydrogenchloride; In methanol; water; Inert atmosphere;
 

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