(2S)-[(2S)-(2-naphthyl)methoxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxo-oxetane-(2R)-carbonyl]amino}pentanoic acid benzyl ester

Base Information

• Chemical Name: (2S)-[(2S)-(2-naphthyl)methoxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxo-oxetane-(2R)-carbonyl]amino}pentanoic acid benzyl ester
• CAS No.: 1350629-57-0
• Molecular Formula: C₃₅H₄₁N₃O₈
• Molecular Weight: 631.726
• Mol file: 1350629-57-0.mol

Synonyms:(2S)-[(2S)-(2-naphthyl)methoxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxo-oxetane-(2R)-carbonyl]amino}pentanoic acid benzyl ester

Chemical Property of (2S)-[(2S)-(2-naphthyl)methoxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxo-oxetane-(2R)-carbonyl]amino}pentanoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-[(2S)-(2-naphthyl)methoxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxo-oxetane-(2R)-carbonyl]amino}pentanoic acid benzyl ester

There total 6 articles about (2S)-[(2S)-(2-naphthyl)methoxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxo-oxetane-(2R)-carbonyl]amino}pentanoic acid benzyl 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: 33.0%

C27H31N3O5 + (2R,3S,4S)-2-hydroxy-4-methyl-3-phenylsulfanylcarbonylhexanoic acid (725240-16-4) → (2S)-[(2S)-(2-naphthyl)methoxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxo-oxetane-(2R)-carbonyl]amino}pentanoic acid benzyl ester (1350629-57-0)

Guidance literature:

With trimethyl phosphite; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; Cooling; Inert atmosphere;

DOI:10.1039/c1ob05661a

Reference yield:

((2S)-naphthylmethoxycarbonylamino)propionic acid (1350629-56-9) → (2S)-[(2S)-(2-naphthyl)methoxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxo-oxetane-(2R)-carbonyl]amino}pentanoic acid benzyl ester (1350629-57-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

1.2: 16 h / 0 - 20 °C

2.1: hydrogenchloride / ethyl acetate / 12 h / 20 °C / Inert atmosphere

3.1: trimethyl phosphite; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane; N,N-dimethyl-formamide / 20 °C / Cooling; Inert atmosphere

With trimethyl phosphite; hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1039/c1ob05661a

Reference yield:

2-naphthylmethoxycarbonyl-(S)-alanyl-(S)-(Nδ-tert-butyloxycarbonyl)ornithine benzyl ester (1350629-65-0) → (2S)-[(2S)-(2-naphthyl)methoxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxo-oxetane-(2R)-carbonyl]amino}pentanoic acid benzyl ester (1350629-57-0)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / ethyl acetate / 12 h / 20 °C / Inert atmosphere

2: trimethyl phosphite; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane; N,N-dimethyl-formamide / 20 °C / Cooling; Inert atmosphere

With trimethyl phosphite; hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1039/c1ob05661a

upstream raw materials:

(2R,3S,4S)-2-hydroxy-4-methyl-3-phenylsulfanylcarbonylhexanoic acid

((2S)-naphthylmethoxycarbonylamino)propionic acid

2-naphthylmethoxycarbonyl-(S)-alanyl-(S)-(Nδ-tert-butyloxycarbonyl)ornithine benzyl ester

naphthalene-2-methyloxy chloroformate