benzyl [(2S)-1-({(2S,3R,4R)-3-hydroxy-5-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}-4-[(4-methoxybenzyl)amino]-5-oxo-1-phenylpentan-2-yl}amino)-3,3-dimethyl-1-oxobutan-2-yl]carbamate (non-preferred name)

Base Information

• Chemical Name: benzyl [(2S)-1-({(2S,3R,4R)-3-hydroxy-5-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}-4-[(4-methoxybenzyl)amino]-5-oxo-1-phenylpentan-2-yl}amino)-3,3-dimethyl-1-oxobutan-2-yl]carbamate (non-preferred name)
• CAS No.: 164514-52-7
• Molecular Formula: C₄₂H₅₀N₄O₇
• Molecular Weight: 722.882
• Mol file: 164514-52-7.mol

Synonyms:SDZ 283053;SDZ-PRI 053

Chemical Property of benzyl [(2S)-1-({(2S,3R,4R)-3-hydroxy-5-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}-4-[(4-methoxybenzyl)amino]-5-oxo-1-phenylpentan-2-yl}amino)-3,3-dimethyl-1-oxobutan-2-yl]carbamate (non-preferred name)

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 977.3°C at 760 mmHg
• Flash Point: 544.8°C
• Density: 1.26g/cm³

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of benzyl [(2S)-1-({(2S,3R,4R)-3-hydroxy-5-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}-4-[(4-methoxybenzyl)amino]-5-oxo-1-phenylpentan-2-yl}amino)-3,3-dimethyl-1-oxobutan-2-yl]carbamate (non-preferred name)

There total 11 articles about benzyl [(2S)-1-({(2S,3R,4R)-3-hydroxy-5-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}-4-[(4-methoxybenzyl)amino]-5-oxo-1-phenylpentan-2-yl}amino)-3,3-dimethyl-1-oxobutan-2-yl]carbamate (non-preferred name) 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: 71.0%

(S)-N-carbobenzoxy-tert-butylleucine (62965-10-0) + (2R,3R,4S)-4-Amino-3-hydroxy-2-(4-methoxy-benzylamino)-5-phenyl-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide; hydrochloride → SDZ PRI-053 (164514-52-7)

Guidance literature:

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 12h; Ambient temperature;

DOI:10.1021/jm9508696

Reference yield:

trans-1-aminoindan-2-ol (7480-35-5,13286-59-4,74165-73-4,126456-43-7,136030-00-7,140632-19-5,140632-20-8) → SDZ PRI-053 (164514-52-7)

Guidance literature:

Multi-step reaction with 7 steps

2: 91 percent / Et₃N / dimethylformamide / 1 h / Ambient temperature

3: 92 percent / SOCl₂ / CH₂Cl₂ / 3 h / Ambient temperature

4: 92 percent / 20percent H₂SO₄ / CH₂Cl₂ / 10 h / Heating

5: 55 percent / 1-hydroxybenzotriazole, N-ethyl-N'-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 72 h / Ambient temperature

6: 96 percent / 3N HCl / CH₂Cl₂; methanol; diethyl ether / 3 h / Ambient temperature

7: 71 percent / PyBOP, diisopropylethylamine / dimethylformamide / 12 h / Ambient temperature

With hydrogenchloride; thionyl chloride; sulfuric acid; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm9508696

Reference yield:

(1S,2S)-1-amino-2,3-dihydro-1H-inden-2-ol (163061-74-3) → SDZ PRI-053 (164514-52-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / Et₃N / dimethylformamide / 1 h / Ambient temperature

2: 92 percent / SOCl₂ / CH₂Cl₂ / 3 h / Ambient temperature

3: 92 percent / 20percent H₂SO₄ / CH₂Cl₂ / 10 h / Heating

4: 55 percent / 1-hydroxybenzotriazole, N-ethyl-N'-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 72 h / Ambient temperature

5: 96 percent / 3N HCl / CH₂Cl₂; methanol; diethyl ether / 3 h / Ambient temperature

6: 71 percent / PyBOP, diisopropylethylamine / dimethylformamide / 12 h / Ambient temperature

With hydrogenchloride; thionyl chloride; sulfuric acid; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm9508696

upstream raw materials:

(S)-N-carbobenzoxy-tert-butylleucine

trans-1-aminoindan-2-ol

(1S,2S)-1-amino-2,3-dihydro-1H-inden-2-ol

(1S,2R)-1-amino-2-indanol

Refernces