(2S,3S)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester

Base Information

• Chemical Name: (2S,3S)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester
• CAS No.: 62182-54-1
• Molecular Formula: C13H15NO5
• Molecular Weight: 265.266
• Mol file: 62182-54-1.mol

Synonyms:N-CBZ-(3S)-3-hydroxproline;N-Cbz-3-hydroxyproline;(2S,3S)-3-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester;N-(benzyloxycarbonyl)-trans-3-hydroxy-L-proline;

Chemical Property of (2S,3S)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester

Chemical Property:

• Boiling Point: 486.9±45.0 °C(Predicted)
• PKA: 3.67±0.40(Predicted)
• PSA: 87.07000
• Density: 1.416±0.06 g/cm3(Predicted)
• LogP: 0.78090

Purity/Quality:

97% ^*data from raw suppliers

(2S,3S)-1-((Benzyloxy)carbonyl)-3-hydroxypyrrolidine-2-carboxylicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,3S)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester

There total 3 articles about (2S,3S)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.5%

benzyl chloroformate (501-53-1,94274-21-2) → (2S,3S)-1-((benzyloxy)carbonyl)-3-hydroxypyrrolidine-2-carboxylic acid (62182-54-1)

Guidance literature:

trans-3-hydroxy-L-proline; With sodium hydroxide; In water; at 13 - 20 ℃;

benzyl chloroformate; In water; at 25 ℃; for 2.25h;

With hydrogenchloride; In water; at 22 ℃; for 3.08333h; pH=3.6;

Reference yield: 78.0%

trans-3-hydroxy-L-proline (4298-08-2) + benzyl chloroformate (501-53-1,94274-21-2) → (2S,3S)-1-((benzyloxy)carbonyl)-3-hydroxypyrrolidine-2-carboxylic acid (62182-54-1)

Guidance literature:

With sodium hydrogencarbonate; In water; for 20h;

DOI:10.1002/ejoc.201402429

Reference yield:

dibenzyl dicarbonate (31139-36-3) + trans-3-hydroxy-L-proline (4298-08-2) → (2S,3S)-1-((benzyloxy)carbonyl)-3-hydroxypyrrolidine-2-carboxylic acid (62182-54-1)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 8h;

DOI:10.1016/j.bmcl.2019.126933

upstream raw materials:

benzyl chloroformate

trans-3-hydroxy-L-proline

dibenzyl dicarbonate

Downstream raw materials:

N-CBZ-(3S)-3-hydroxprolinamide

1-benzyloxycarbonyl-(2R)-tert-butyldimethylsilyloxymethyl-(3S)-hydroxypyrrolidine

3-methoxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

C₂₀H₂₁NO₅