Glycine, N-[1-[(phenylmethoxy)carbonyl]-L-prolyl]-, methyl ester

Base Information

• Chemical Name: Glycine, N-[1-[(phenylmethoxy)carbonyl]-L-prolyl]-, methyl ester
• CAS No.: 61058-42-2
• Molecular Formula: C16H20N2O5
• Molecular Weight: 320.345
• Mol file: 61058-42-2.mol

Synonyms:N-(1-benzyloxycarbonyl-L-prolyl)-glycine methyl ester;N-(1-Benzyloxycarbonyl-L-prolyl)-glycin-methylester;Z-Pro-Gly-OMe;Cbz-Pro-Gly-OMe;

Chemical Property of Glycine, N-[1-[(phenylmethoxy)carbonyl]-L-prolyl]-, methyl ester

Chemical Property:

• PSA: 84.94000
• LogP: 1.40560

Purity/Quality:

CARBOBENZYLOXYPROLYLGLYCINE METHYL ESTER Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Glycine, N-[1-[(phenylmethoxy)carbonyl]-L-prolyl]-, methyl ester

There total 9 articles about Glycine, N-[1-[(phenylmethoxy)carbonyl]-L-prolyl]-, methyl 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: 51.0%

methoxycarbonylmethylamine (616-34-2) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → Z-Pro-Gly-OMe (61058-42-2)

Guidance literature:

N-Benzyloxycarbonyl-L-proline; With bis(2-chlorophenyl)borinic acid; In fluorobenzene; at 65 ℃; for 0.25h; Inert atmosphere; Molecular sieve;

methoxycarbonylmethylamine; In fluorobenzene; at 65 ℃; for 48h; Inert atmosphere; Molecular sieve;

DOI:10.1039/c5cc06177f

Reference yield:

glycine ethyl ester hydrochloride (5680-79-5,883886-67-7) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → Z-Pro-Gly-OMe (61058-42-2)

Guidance literature:

With 4-methyl-morpholine; Isopropenyl chloroformate; triethylamine; Yield given. Multistep reaction; 1.) THF, RT, 4 min; 2.) THF, RT, 2.5 h;

Reference yield:

methanol (67-56-1) + Nα-benzyloxycarbonyl-L-prolyl-glycinamide (35010-96-9) → Z-Pro-Gly-OMe (61058-42-2) + N-carbobenzoxyprolylglycine (2766-18-9)

Guidance literature:

With peptide amidase from Stenotrophomonas maltophilia; Sucrose; In N,N-dimethyl-formamide; acetonitrile; at 30 ℃; for 16h; Molecular sieve; Enzymatic reaction;

DOI:10.1002/adsc.201400109

upstream raw materials:

chloroformic acid ethyl ester

N-Benzyloxycarbonyl-L-proline

glycine ethyl ester hydrochloride

1-benzyl hydrogen (S)-pyrrolidine-1,2-dicarboxylate, compound with dicyclohexylamine (1:1)

Downstream raw materials:

N-benzyloxycarbonyl-prolyl-glycylglycine

N-carbobenzoxyprolylglycine

(3S,6S)-3-methoxy-1,6-trimethylene-2,5-piperazinedione

Cbz-L-Pro-Gly(OMe)-OMe

Refernces

• 1、 Kon, Kazumasa,Kohari, Yoshihito,Murata, Miki. "Unnatural tripeptide as highly enantioselective organocatalyst for asymmetric aldol reaction of isatins". supporting information. p. 415 - 418. Retrieved 2019/01/05.
• 2、 Arif, Muhammad I.,Toplak, Ana,Szymanski, Wiktor,Feringa, Ben L.,Nuijens, Timo,Quaedflieg, Peter J. L. M.,Wu, Bian,Janssen, Dick B.. "One-step C-terminal deprotection and activation of peptides with peptide amidase from stenotrophomonas maltophilia in neat organic solvent". . p. 2197 - 2202. Retrieved 2014/07/21.