1-CBZ-4(R)-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID ETHYL ESTER

Base Information

• Chemical Name: 1-CBZ-4(R)-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID ETHYL ESTER
• CAS No.: 103667-57-8
• Molecular Formula: C15H19 N O5
• Molecular Weight: 293.32
• Hs Code.: 2933990090
• Mol file: 103667-57-8.mol

Synonyms:1,2-Pyrrolidinedicarboxylicacid, 4-hydroxy-, 2-ethyl 1-(phenylmethyl) ester, (2S-trans)-

Chemical Property of 1-CBZ-4(R)-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID ETHYL ESTER

Chemical Property:

• Boiling Point: 434.1±45.0 °C(Predicted)
• PKA: 14.28±0.40(Predicted)
• PSA: 76.07000
• Density: 1.279±0.06 g/cm3(Predicted)
• LogP: 1.25940
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

1-Cbz-trans-4-Hydroxy-L-proline ethyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-CBZ-4(R)-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID ETHYL ESTER

There total 6 articles about 1-CBZ-4(R)-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID ETHYL 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: 100.0%

ethanol (64-17-5) + (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (13504-85-3) → (2S,4R)-ethyl N1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylate (103667-57-8)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; for 16h; Heating;

DOI:10.1021/jm00106a037

Reference yield: 83.0%

trans-4-hydroxy-L-proline ethyl ester hydrochloride (33996-30-4) + benzyl chloroformate (501-53-1,94274-21-2) → (2S,4R)-ethyl N1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylate (103667-57-8)

Guidance literature:

With potassium carbonate; In diethyl ether; water; at 0 - 20 ℃; for 2h;

Reference yield: 81.0%

ethyl iodide (75-03-6) + (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (13504-85-3) → (2S,4R)-ethyl N1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylate (103667-57-8)

Guidance literature:

With triethylamine; In acetonitrile; at 55 ℃;

DOI:10.1021/jm9601765

upstream raw materials:

ethanol

(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

ethyl iodide

4R-4-hydroxyproline

Downstream raw materials:

cis-N-(benzyloxycarbonyl)-4-carboxy-L-proline methyl ester

C₁₅H₁₉NO₅

C₂₁H₂₃NO₄

C₂₈H₂₉NO₄

Refernces

• 1、 -. "SUBSTITUTED HETEROCYCLIC SULFONAMIDE COMPOUNDS USEFUL AS TRPA1 MODULATORS". Paragraph 01295; 01296. . Retrieved 2015/04/28.
• 2、 Anas, Andrea Roxanne J.,Kisugi, Takaya,Umezawa, Taiki,Matsuda, Fuyuhiko,Okino, Tatsufumi,Campitelli, Marc R.,Quinn, Ronald J.. "Thrombin inhibitors from the freshwater cyanobacterium Anabaena compacta". . p. 1546 - 1552,7. Retrieved 2012/12/12.