tert-butyl [(2S,3S,5R)-6-({(2S,3S)-1-[(1H-benzimidazol-2-ylmethyl)amino]-3-methyl-1-oxopentan-2-yl}amino)-5-benzyl-3-hydroxy-6-oxo-1-phenylhexan-2-yl]carbamate

Base Information

• Chemical Name: tert-butyl [(2S,3S,5R)-6-({(2S,3S)-1-[(1H-benzimidazol-2-ylmethyl)amino]-3-methyl-1-oxopentan-2-yl}amino)-5-benzyl-3-hydroxy-6-oxo-1-phenylhexan-2-yl]carbamate
• CAS No.: 126409-81-2
• Molecular Formula: C38H49 N5 O5
• Molecular Weight: 655.8262
• Mol file: 126409-81-2.mol

Synonyms:Carbamicacid,[5-[[1-[[(1H-benzimidazol-2-ylmethyl)amino]carbonyl]-2-methylbutyl]amino]-2-hydroxy-5-oxo-1,4-bis(phenylmethyl)pentyl]-,1,1-dimethylethyl ester, [1S-[1R*,2R*,4S*,5(1R*,2R*)]]-

Chemical Property of tert-butyl [(2S,3S,5R)-6-({(2S,3S)-1-[(1H-benzimidazol-2-ylmethyl)amino]-3-methyl-1-oxopentan-2-yl}amino)-5-benzyl-3-hydroxy-6-oxo-1-phenylhexan-2-yl]carbamate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 941.5°Cat760mmHg
• Flash Point: 523.2°C
• Density: 1.184g/cm³

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyl [(2S,3S,5R)-6-({(2S,3S)-1-[(1H-benzimidazol-2-ylmethyl)amino]-3-methyl-1-oxopentan-2-yl}amino)-5-benzyl-3-hydroxy-6-oxo-1-phenylhexan-2-yl]carbamate

There total 7 articles about tert-butyl [(2S,3S,5R)-6-({(2S,3S)-1-[(1H-benzimidazol-2-ylmethyl)amino]-3-methyl-1-oxopentan-2-yl}amino)-5-benzyl-3-hydroxy-6-oxo-1-phenylhexan-2-yl]carbamate 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: 98.0%

[(1S,2S,4R)-4-{(S)-1-[(1H-Benzoimidazol-2-ylmethyl)-carbamoyl]-2-methyl-butylcarbamoyl}-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentyl]-carbamic acid tert-butyl ester (126410-69-3) → N'-(2-benzimidazolylmethyl)-N-<5(S)-<(tert-butoxycarbonyl)amino>-4(S)-hydroxy-6-phenyl-2(R)-(phenylmethyl)hexanoyl>isoleucine amide (126409-81-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 20h; Ambient temperature;

DOI:10.1021/jm00113a025

Reference yield:

2-<(L-isoleucino)methyl>benzimidazole (135832-61-0) → N'-(2-benzimidazolylmethyl)-N-<5(S)-<(tert-butoxycarbonyl)amino>-4(S)-hydroxy-6-phenyl-2(R)-(phenylmethyl)hexanoyl>isoleucine amide (126409-81-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / 1-hydroxybenzotriazole (HOBT), 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride (EDC), triethylamine / dimethylformamide / 20 h / Ambient temperature

2: 98 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 20 h / Ambient temperature

With tetrabutyl ammonium fluoride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm00113a025

Reference yield:

tert-(butoxycarbonyl)isoleucine succinimidyl ester (3392-08-3) → N'-(2-benzimidazolylmethyl)-N-<5(S)-<(tert-butoxycarbonyl)amino>-4(S)-hydroxy-6-phenyl-2(R)-(phenylmethyl)hexanoyl>isoleucine amide (126409-81-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / triethylamine / 1,2-dimethoxy-ethane / 18 h / Ambient temperature

2: 86 percent / HCl (gas) / ethyl acetate / 0.33 h / -25 °C

3: 82 percent / 1-hydroxybenzotriazole (HOBT), 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride (EDC), triethylamine / dimethylformamide / 20 h / Ambient temperature

4: 98 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 20 h / Ambient temperature

With hydrogenchloride; tetrabutyl ammonium fluoride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00113a025

upstream raw materials:

[(1S,2S,4R)-4-{(S)-1-[(1H-Benzoimidazol-2-ylmethyl)-carbamoyl]-2-methyl-butylcarbamoyl}-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentyl]-carbamic acid tert-butyl ester

tert-(butoxycarbonyl)isoleucine succinimidyl ester

N-tert-butyloxy-isoleucine

2-<(L-isoleucino)methyl>benzimidazole