Carbamic acid,[(1S,2S,4R)-2-hydroxy-4-[4-(2-methyl-1-oxopropyl)-1H-imidazol-2-yl]-5-phenyl-1-(phenylmethyl)pentyl]-,1,1-dimethylethyl ester (9CI)

Base Information

• Chemical Name: Carbamic acid,[(1S,2S,4R)-2-hydroxy-4-[4-(2-methyl-1-oxopropyl)-1H-imidazol-2-yl]-5-phenyl-1-(phenylmethyl)pentyl]-,1,1-dimethylethyl ester (9CI)
• CAS No.: 150348-85-9
• Molecular Formula: C30H39 N3 O4
• Molecular Weight: 505.657
• Mol file: 150348-85-9.mol

Synonyms:Carbamic acid,[2-hydroxy-4-[4-(2-methyl-1-oxopropyl)-1H-imidazol-2-yl]-5-phenyl-1-(phenylmethyl)pentyl]-,1,1-dimethylethyl ester, [1S-(1R*,2R*,4S*)]-; SB 205891

Chemical Property of Carbamic acid,[(1S,2S,4R)-2-hydroxy-4-[4-(2-methyl-1-oxopropyl)-1H-imidazol-2-yl]-5-phenyl-1-(phenylmethyl)pentyl]-,1,1-dimethylethyl ester (9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Carbamic acid,[(1S,2S,4R)-2-hydroxy-4-[4-(2-methyl-1-oxopropyl)-1H-imidazol-2-yl]-5-phenyl-1-(phenylmethyl)pentyl]-,1,1-dimethylethyl ester (9CI)

There total 5 articles about Carbamic acid,[(1S,2S,4R)-2-hydroxy-4-[4-(2-methyl-1-oxopropyl)-1H-imidazol-2-yl]-5-phenyl-1-(phenylmethyl)pentyl]-,1,1-dimethylethyl ester (9CI) 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: 100.0%

2-<(1R,3S,4S)-1-benzyl-4<(tert-butoxycarbonyl)amino>-3-(tert-butyldimethylsiloxy)-5-phenylpentyl>-5-(2-methylpropionyl)imidazole (150349-10-3) → [(1S,2S,4R)-1-Benzyl-2-hydroxy-4-(5-isobutyryl-1H-imidazol-2-yl)-5-phenyl-pentyl]-carbamic acid tert-butyl ester (150348-85-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50 ℃; for 5h;

DOI:10.1021/jm00045a015

Reference yield:

N-(1,1-dimethylethoxycarbonyl)-5(S)-amino-4(S)-(t-butyldimethylsilyloxy)-6-phenyl-2(R)-(phenylmethyl)hexanoic acid (98818-51-0) → [(1S,2S,4R)-1-Benzyl-2-hydroxy-4-(5-isobutyryl-1H-imidazol-2-yl)-5-phenyl-pentyl]-carbamic acid tert-butyl ester (150348-85-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 57 percent / 1-hydroxybenzotriazole, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 24 h / Ambient temperature

2: 1.) H₂, 2.) NaOH / 1.) palladium black / 1.) EtOH, 23 h, 2.) EtOH, reflux, 3 h

3: 93 percent / tetrahydrofuran; diethyl ether / 0.25 h

4: 90 percent / MnO₂ / CH₂Cl₂ / Ambient temperature

5: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 5 h / 50 °C

With manganese(IV) oxide; sodium hydroxide; tetrabutyl ammonium fluoride; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00045a015

Reference yield:

(2R,4S,5S)-2-benzyl-5-<(tert-butoxycarbonyl)amino>-4-(tert-butyldimethylsiloxy)-N-(isoxazol-4-yl)-6-phenylhexanamide (149976-34-1) → [(1S,2S,4R)-1-Benzyl-2-hydroxy-4-(5-isobutyryl-1H-imidazol-2-yl)-5-phenyl-pentyl]-carbamic acid tert-butyl ester (150348-85-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) H₂, 2.) NaOH / 1.) palladium black / 1.) EtOH, 23 h, 2.) EtOH, reflux, 3 h

2: 93 percent / tetrahydrofuran; diethyl ether / 0.25 h

3: 90 percent / MnO₂ / CH₂Cl₂ / Ambient temperature

4: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 5 h / 50 °C

With manganese(IV) oxide; sodium hydroxide; tetrabutyl ammonium fluoride; hydrogen; palladium; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jm00045a015

upstream raw materials:

2-<(1R,3S,4S)-1-benzyl-4<(tert-butoxycarbonyl)amino>-3-(tert-butyldimethylsiloxy)-5-phenylpentyl>-5-(2-methylpropionyl)imidazole

N-(1,1-dimethylethoxycarbonyl)-5(S)-amino-4(S)-(t-butyldimethylsilyloxy)-6-phenyl-2(R)-(phenylmethyl)hexanoic acid

2-<(2R,3S,4S)-1-benzyl-4-<(tert-butoxycarbonyl)amino>-3-(tert-butyldimethylsiloxy)-5-phenylpentyl>-5-formylimidazole

(2R,4S,5S)-2-benzyl-5-<(tert-butoxycarbonyl)amino>-4-(tert-butyldimethylsiloxy)-N-(isoxazol-4-yl)-6-phenylhexanamide

Downstream raw materials:

2-<(1R,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-phenylpentyl>-5-(2-methylpropionyl)imidazole