5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-1H-indole-5-carbonyl}-amino)-3-phenyl-propionylamino]-isophthalic acid dibenzyl ester

Base Information

• Chemical Name: 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-1H-indole-5-carbonyl}-amino)-3-phenyl-propionylamino]-isophthalic acid dibenzyl ester
• CAS No.: 167992-88-3
• Molecular Formula: C₅₂H₅₀N₄O₇
• Molecular Weight: 842.992
• Mol file: 167992-88-3.mol

Synonyms:5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-1H-indole-5-carbonyl}-amino)-3-phenyl-propionylamino]-isophthalic acid dibenzyl ester

Chemical Property of 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-1H-indole-5-carbonyl}-amino)-3-phenyl-propionylamino]-isophthalic acid dibenzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-1H-indole-5-carbonyl}-amino)-3-phenyl-propionylamino]-isophthalic acid dibenzyl ester

There total 6 articles about 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-1H-indole-5-carbonyl}-amino)-3-phenyl-propionylamino]-isophthalic acid dibenzyl ester 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: 69.0%

adamantylmethylamine (17768-41-1) + 5-(1S-(3,5-dibenzyloxycarbonylphenylaminocarbonyl)-2-phenylethylaminocarbonyl)-indole-6-carboxylic acid (167992-95-2) → 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-1H-indole-5-carbonyl}-amino)-3-phenyl-propionylamino]-isophthalic acid dibenzyl ester (167992-88-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1021/jm9508907

Reference yield:

dimethyl 4-methyl-5-nitro-phthalate (167992-81-6) → 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-1H-indole-5-carbonyl}-amino)-3-phenyl-propionylamino]-isophthalic acid dibenzyl ester (167992-88-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / dimethylformamide / 6 h / 150 °C

2: 99 percent / H₂ / 10percent Pd/C / toluene / 1 h / Ambient temperature

3: NaOH / H₂O; ethanol / 3 h / Heating

4: 0.17 h / Heating

5: 57 percent / acetonitrile / 3.5 h / Heating

6: 69 percent / bromotris(pyrrolidino)phosphonium hexafluorophosphate, diisopropylethylamine / CH₂Cl₂ / 24 h / Ambient temperature

With sodium hydroxide; hydrogen; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; palladium on activated charcoal; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jm9508907

Reference yield:

dimethyl 3-<2-(N,N-dimethylamino)ethylene>-4-nitrophthalate → 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-1H-indole-5-carbonyl}-amino)-3-phenyl-propionylamino]-isophthalic acid dibenzyl ester (167992-88-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / H₂ / 10percent Pd/C / toluene / 1 h / Ambient temperature

2: NaOH / H₂O; ethanol / 3 h / Heating

3: 0.17 h / Heating

4: 57 percent / acetonitrile / 3.5 h / Heating

5: 69 percent / bromotris(pyrrolidino)phosphonium hexafluorophosphate, diisopropylethylamine / CH₂Cl₂ / 24 h / Ambient temperature

With sodium hydroxide; hydrogen; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; palladium on activated charcoal; In ethanol; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/jm9508907

upstream raw materials:

adamantylmethylamine

5-(1S-(3,5-dibenzyloxycarbonylphenylaminocarbonyl)-2-phenylethylaminocarbonyl)-indole-6-carboxylic acid

dimethyl indole-5,6-dicarboxylate

indole-5,6-dicarboxylic acid anhydride

Downstream raw materials:

1-methyl-5-[[[1(S)-[[[3,5-bis(benzyloxycarbonyl)phenyl]amino]carbonyl]-2-phenylethyl]amino]carbonyl]-6-[[(1-adamantylmethyl)amino]carbonyl]indole

Refernces