(2S,4S)-BOC-4-CYCLOHEXYL-PYRROLIDINE-2-CARBOXYLIC ACID

Base Information

• Chemical Name: (2S,4S)-BOC-4-CYCLOHEXYL-PYRROLIDINE-2-CARBOXYLIC ACID
• CAS No.: 394734-77-1
• Molecular Formula: C₁₆H₂₇NO₄
• Molecular Weight: 297.395
• Mol file: 394734-77-1.mol

Synonyms:(2S,4S)-BOC-4-CYCLOHEXYL-PYRROLIDINE-2-CARBOXYLIC ACID;(2S,4S)-Boc-4-cyclohexyl-Pro-OH

Chemical Property of (2S,4S)-BOC-4-CYCLOHEXYL-PYRROLIDINE-2-CARBOXYLIC ACID

Chemical Property:

• PSA: 66.84000
• LogP: 3.21480

Purity/Quality:

98% ^*data from raw suppliers

Boc-L-Pro(4-Chx)-OH(2S,4S) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S,4S)-Boc-4-cyclohexyl-pyrrolidine-2-carboxylic Acid is used in preparation of proline-containg peptides as granzyme B inhibitors.

Technology Process of (2S,4S)-BOC-4-CYCLOHEXYL-PYRROLIDINE-2-CARBOXYLIC ACID

There total 10 articles about (2S,4S)-BOC-4-CYCLOHEXYL-PYRROLIDINE-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: 90.0%

N-Boc-4-cyclohexyl-L-proline methyl ester → N-Boc-4-cyclohexyl-L-proline (394734-77-1)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 6h;

Reference yield: 89.0%

1-tert-butyl 2-ethyl (2S,4S)-4-cyclohexyl-1,2-pyrrolidinedicarboxylate (934470-78-7) → (2S,4S)-4-cyclohexyl-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid (934470-83-4,394734-77-1)

Guidance literature:

With sodium hydroxide; In methanol; water; at 20 ℃; for 6h;

DOI:10.1016/j.bmc.2007.01.033

Reference yield: 87.0%

di-tert-butyl dicarbonate (24424-99-5) + trans-4-cyclohexyl-L-proline hydrochloride (90657-55-9) → (2S,4S)-1-(tert-butoxycarbonyl)-4-cyclohexylpyrrolidine-2-carboxylic acid (394734-77-1)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 0 - 25 ℃;

upstream raw materials:

1-tert-butyl 2-ethyl (2S,4S)-4-cyclohexyl-1,2-pyrrolidinedicarboxylate

1-tert-butyl 2-ethyl (2S,4R)-4-cyclohexyl-5-oxo-1,2-pyrrolidinedicarboxylate

cyclohexanone

(S)-ethyl N-tert-butoxycarbonylpyroglutamate

Refernces

• 1、 -. "Proline compounds as Granzyme B inhibitors". Page/Page column 54; 55. . Retrieved 2016/10/27.
• 2、 -. "Novel peptides as NS3-serine protease inhibitors of hepatitis C virus". . . Retrieved 2008/06/13.