N-[5-(tert-butoxycarbonyl)aminopentyl]-2(R)-(carbobenzoxy)amino-4-methylpentanamide

Base Information

• Chemical Name: N-[5-(tert-butoxycarbonyl)aminopentyl]-2(R)-(carbobenzoxy)amino-4-methylpentanamide
• CAS No.: 294625-17-5
• Molecular Formula: C₂₄H₃₉N₃O₅
• Molecular Weight: 449.591
• Mol file: 294625-17-5.mol

Synonyms:N-[5-(tert-butoxycarbonyl)aminopentyl]-2(R)-(carbobenzoxy)amino-4-methylpentanamide

Chemical Property of N-[5-(tert-butoxycarbonyl)aminopentyl]-2(R)-(carbobenzoxy)amino-4-methylpentanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[5-(tert-butoxycarbonyl)aminopentyl]-2(R)-(carbobenzoxy)amino-4-methylpentanamide

There total 1 articles about N-[5-(tert-butoxycarbonyl)aminopentyl]-2(R)-(carbobenzoxy)amino-4-methylpentanamide 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: 89.0%

2(R)-(carbobenzoxy)amino-4-methylpentanoic acid p-nitrophenyl ester (52235-17-3) + 5-tert-butoxycarbonylamino-1-aminopentane (51644-96-3) → N-[5-(tert-butoxycarbonyl)aminopentyl]-2(R)-(carbobenzoxy)amino-4-methylpentanamide (294625-17-5)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 5h;

DOI:10.1021/jm990356p

Reference yield:

N-[5-(tert-butoxycarbonyl)aminopentyl]-2(R)-(carbobenzoxy)amino-4-methylpentanamide (294625-17-5) → N-[1-(5-aminopentylcarbamoyl)-3-methyl-1(R)-butyl]-1(S)-phenyl-2(R)-[(8-hydroxy-6(R),11(R)-dimethyl-1,2,5,6-tetrahydro-4H-2(R),6-methanobenzazocin-3-yl)methyl]cyclopropanecarboxamide

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / H₂ / 10percent Pd/C / methanol / 0.75 h / 20 °C / 760.05 Torr

2: HOBt; DCC / dimethylformamide / 48 h / 0 - 5 °C

3: aq. TFA / methoxybenzene / 20 °C

With hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; trifluoroacetic acid; 10percent Pd/C; In methanol; methoxybenzene; N,N-dimethyl-formamide; 1: Hydrogenolysis / 2: Acylation / 3: Hydrolysis;

DOI:10.1021/jm990356p

Reference yield:

N-[5-(tert-butoxycarbonyl)aminopentyl]-2(R)-(carbobenzoxy)amino-4-methylpentanamide (294625-17-5) → N-[1-(5-guanidinopentylcarbamoyl)-3-methyl-1(R)-butyl]-1(S)-phenyl-2(R)-[(8-hydroxy-6(R),11(R)-dimethyl-1,2,5,6-tetrahydro-4H-2(R),6-methanobenzazocin-3-yl)methyl]cyclopropanecarboxamide

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / H₂ / 10percent Pd/C / methanol / 0.75 h / 20 °C / 760.05 Torr

2: HOBt; DCC / dimethylformamide / 48 h / 0 - 5 °C

3: aq. TFA / methoxybenzene / 20 °C

4: 52 percent / DIEA / ethanol / 48 h / 60 °C / pH 10

With hydrogen; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; 10percent Pd/C; In methanol; ethanol; methoxybenzene; N,N-dimethyl-formamide; 1: Hydrogenolysis / 2: Acylation / 3: Hydrolysis / 4: amidination;

DOI:10.1021/jm990356p

upstream raw materials:

2(R)-(carbobenzoxy)amino-4-methylpentanoic acid p-nitrophenyl ester

5-tert-butoxycarbonylamino-1-aminopentane