(L)-N-BENZYLOXYCARBONYL-PROLINE-TERT BUTYLAMIDE

Base Information

• Chemical Name: (L)-N-BENZYLOXYCARBONYL-PROLINE-TERT BUTYLAMIDE
• CAS No.: 128018-17-7
• Molecular Formula: C17H24N2O3
• Molecular Weight: 304.38400
• Mol file: 128018-17-7.mol

Synonyms:(S)-1-azido-5,6-epoxyhexane;Oxirane,(4-azidobutyl)-,(S);(S)-1-benzyloxycarbonyl-2-t-butylaminocarbonylpyrrolidine;

Chemical Property of (L)-N-BENZYLOXYCARBONYL-PROLINE-TERT BUTYLAMIDE

Chemical Property:

• PSA: 58.64000
• LogP: 3.03110

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (L)-N-BENZYLOXYCARBONYL-PROLINE-TERT BUTYLAMIDE

There total 3 articles about (L)-N-BENZYLOXYCARBONYL-PROLINE-TERT BUTYLAMIDE 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: 95.0%

tert-butylamine (75-64-9) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → Z-Pro-NHtBu (128018-17-7)

Guidance literature:

With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 16h; Inert atmosphere;

DOI:10.1039/c4cc03261f

Reference yield:

N-Benzyloxycarbonyl-L-proline (1148-11-4) → Z-Pro-NHtBu (128018-17-7)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / tetrahydrofuran / 0.5 h / 5 - 10 °C

2: tetrahydrofuran / 1 h / 10 °C

With triethylamine; In tetrahydrofuran;

DOI:10.1016/0022-328X(92)80121-D

Reference yield:

(S)-2-Ethoxycarbonyloxycarbonyl-pyrrolidine-1-carboxylic acid benzyl ester + tert-butylamine (75-64-9) → Z-Pro-NHtBu (128018-17-7)

Guidance literature:

In tetrahydrofuran; at 10 ℃; for 1h; Yield given;

DOI:10.1016/0022-328X(92)80121-D

upstream raw materials:

tert-butylamine

N-Benzyloxycarbonyl-L-proline

Downstream raw materials:

((S)-1-{(S)-1-[(1S,2S)-1-Benzyl-3-((S)-2-tert-butylcarbamoyl-pyrrolidin-1-yl)-2-hydroxy-3-oxo-propylcarbamoyl]-2-carbamoyl-ethylcarbamoyl}-2-phenyl-ethyl)-carbamic acid benzyl ester

((R)-1-{(S)-1-[(1S,2S)-1-Benzyl-3-((S)-2-tert-butylcarbamoyl-pyrrolidin-1-yl)-2-hydroxy-3-oxo-propylcarbamoyl]-2-carbamoyl-ethylcarbamoyl}-2-phenyl-ethyl)-carbamic acid benzyl ester

Refernces

• 1、 Le Bailly, Bryden A. F.,Clayden, Jonathan. "Controlling the sign and magnitude of screw-sense preference from the C-terminus of an achiral helical foldamer". supporting information. p. 7949 - 7952. Retrieved 2014/07/08.
• 2、 Munegumi, Toratane,Maruyama, Tetsuya,Takasaki, Michiaki,Harada, Kaoru. "Diastereoselective Catalytic Hydrogenation of Nα-Pyruvoyl-(S)-prolinamide". . p. 1832 - 1834. Retrieved 2007/10/02.