(2R,4S)-N-ALPHA-CARBOBENZOXY-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID

Base Information

• Chemical Name: (2R,4S)-N-ALPHA-CARBOBENZOXY-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
• CAS No.: 155153-78-9
• Molecular Formula: C13H15NO5
• Molecular Weight: 265.266
• Mol file: 155153-78-9.mol

Synonyms:(2R,4S)-N-ALPHA-CARBOBENZOXY-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID;N-ALPHA-CARBOBENZOXY-4-HYDROXY-D-PROLINE;Z-D-HYP-OH;(2R,4S)-N-ALPHA-BENZYLOXYCARBONYL-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID;N-CBZ-TRANS-4-HYDROXY-D-PROLINE;(4S)-1-Cbz-4-hydroxy-D-proline

Chemical Property of (2R,4S)-N-ALPHA-CARBOBENZOXY-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID

Chemical Property:

• Boiling Point: 486.9±45.0 °C(Predicted)
• PKA: 3.78±0.40(Predicted)
• PSA: 87.07000
• Density: 1.416±0.06 g/cm3(Predicted)
• LogP: 0.78090

Purity/Quality:

98.5% ^*data from raw suppliers

CBZ-D-HYP-OH 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R,4S)-N-ALPHA-CARBOBENZOXY-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID

There total 6 articles about (2R,4S)-N-ALPHA-CARBOBENZOXY-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID 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: 100.0%

benzyl chloroformate (501-53-1,94274-21-2) + trans-4-hydroxyproline (3398-22-9,30724-02-8) → (4S)-1-[(benzyloxy)carbonyl]-4-hydroxy-D-proline (155153-78-9)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 0 ℃; for 1h;

DOI:10.1021/jm900598m

Reference yield: 71.0%

(2R,4R)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (155075-23-3) → (4S)-1-[(benzyloxy)carbonyl]-4-hydroxy-D-proline (155153-78-9)

Guidance literature:

(2R,4R)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate; With dicyclohexyl-carbodiimide; copper(l) chloride; In 1,4-dioxane; at 40 - 50 ℃; for 48h;

With formic acid; In toluene; for 24h; Reflux;

With sodium hydroxide; In tetrahydrofuran; at 25 ℃; for 0.5h;

DOI:10.1002/pep2.24140

Reference yield:

(2R,4S)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride (142347-81-7,441067-49-8) + benzyl chloroformate (501-53-1,94274-21-2) → (4S)-1-[(benzyloxy)carbonyl]-4-hydroxy-D-proline (155153-78-9)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; Cooling with ice;

upstream raw materials:

benzyl chloroformate

trans-4-hydroxyproline

(2R,4R)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

cis-hydroxy-D-proline

Downstream raw materials:

4S-O⁴(t-butyl)-D-Pro acid

4S-O⁴(t-butyl)-N₁-(fluorenylmethyloxycarbonyl)-D-proline

(2S,4R)-4-fluoro-2-(1,3,5-trimethyl-1H-pyrazol-4-ylmethyl)-pyrrolidine-1-carboxylic acid benzyl ester

(2R,4S)-4-(tert-butyl-dimethyl-silanyloxy)-2-[phenoxythiocarbonyloxy-(1,3,5-trimethyl-1H-pyrazol-4-yl)methyl]-pyrrolidine-1-carboxylic acid benzyl ester

Refernces

• 1、 -. "EP300/CREBBP INHIBITOR". Paragraph 0233; 0234. . Retrieved 2020/05/30.
• 2、 -. "Hydroxamate-Based Inhibitors of Deacetylases". Page/Page column 25-26. . Retrieved 2011/04/18.