benzyl 2S-(6-tert-butoxycarbonylamino)-1-(methoxy-1-oxohexan-2S-ylcarbamoyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: benzyl 2S-(6-tert-butoxycarbonylamino)-1-(methoxy-1-oxohexan-2S-ylcarbamoyl)pyrrolidine-1-carboxylate
• CAS No.: 112920-78-2
• Molecular Formula: C₂₅H₃₇N₃O₇
• Molecular Weight: 491.585
• Mol file: 112920-78-2.mol

Synonyms:benzyl 2S-(6-tert-butoxycarbonylamino)-1-(methoxy-1-oxohexan-2S-ylcarbamoyl)pyrrolidine-1-carboxylate

Chemical Property of benzyl 2S-(6-tert-butoxycarbonylamino)-1-(methoxy-1-oxohexan-2S-ylcarbamoyl)pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2S-(6-tert-butoxycarbonylamino)-1-(methoxy-1-oxohexan-2S-ylcarbamoyl)pyrrolidine-1-carboxylate

There total 2 articles about benzyl 2S-(6-tert-butoxycarbonylamino)-1-(methoxy-1-oxohexan-2S-ylcarbamoyl)pyrrolidine-1-carboxylate 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: 93.0%

(S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate (3017-32-1,1372256-52-4) + Z-proline N-hydroxysuccinimide ester (3397-33-9) → benzyl 2S-(6-tert-butoxycarbonylamino)-1-(methoxy-1-oxohexan-2S-ylcarbamoyl)pyrrolidine-1-carboxylate (112920-78-2)

Guidance literature:

In dichloromethane; ice cooling, 4 h, RT;

Reference yield: 90.0%

N-ε-tert-butoxycarbonyl-L-lysine methyl ester hydrochloride (2389-48-2) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → benzyl 2S-(6-tert-butoxycarbonylamino)-1-(methoxy-1-oxohexan-2S-ylcarbamoyl)pyrrolidine-1-carboxylate (112920-78-2)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/jm400294w

Reference yield: 87.0%

benzyl 2S-(6-tert-butoxycarbonylamino)-1-(methoxy-1-oxohexan-2S-ylcarbamoyl)pyrrolidine-1-carboxylate (112920-78-2) → benzyl 2S-(6-tert-butoxycarbonylamino)-1-(hydroxyhexan-2S-ylcarbamoyl)pyrrolidine-1-carboxylate (1451453-93-2)

Guidance literature:

With sodium tetrahydroborate; lithium chloride; In tetrahydrofuran; ethanol; at 20 ℃; for 16h;

DOI:10.1021/jm400294w

upstream raw materials:

(S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate

Z-proline N-hydroxysuccinimide ester

N-ε-tert-butoxycarbonyl-L-lysine methyl ester hydrochloride

N-Benzyloxycarbonyl-L-proline

Downstream raw materials:

Z-Arg(Adoc)2-Pro-Lys(Boc)

Z-Arg(Adoc)2-Pro-Lys(Boc)-OMe

benzyl 2S-(6-tert-butoxycarbonylamino)-1-(hydroxyhexan-2S-ylcarbamoyl)pyrrolidine-1-carboxylate

trans-benzyl 2S-[(1-tert-butoxycarbonylamino)-7-(phenylsulfonyl)hept-6-en-5S-ylcarbamoyl]pyrrolidine-1-carboxylate

Refernces

• 1、 Franzen, Henry M.,Ragnarsson, Ulf,Nagren, Kjell,Langstroem, Bengt. "11C-Labelling of Substance P. Preparation of a Homocysteine-containing Precursor and its Subsequent Application in the Synthesis of the Labelled Neuropeptide". . p. 2241 - 2248. Retrieved 2007/10/02.