tert-butyl ((1S)-1-benzyl-2-{[(1S)-1-[4-(2-tert-butyl-1,1,3-trioxo-2,3-dihydroisothiazol-5-yl)benzyl]-2-oxo-2-(pentylamino)ethyl]amino}-2-oxoethyl)carbamate

Base Information

• Chemical Name: tert-butyl ((1S)-1-benzyl-2-{[(1S)-1-[4-(2-tert-butyl-1,1,3-trioxo-2,3-dihydroisothiazol-5-yl)benzyl]-2-oxo-2-(pentylamino)ethyl]amino}-2-oxoethyl)carbamate
• CAS No.: 910606-87-0
• Molecular Formula: C₃₅H₄₈N₄O₇S
• Molecular Weight: 668.855

Synonyms:tert-butyl ((1S)-1-benzyl-2-{[(1S)-1-[4-(2-tert-butyl-1,1,3-trioxo-2,3-dihydroisothiazol-5-yl)benzyl]-2-oxo-2-(pentylamino)ethyl]amino}-2-oxoethyl)carbamate

Chemical Property of tert-butyl ((1S)-1-benzyl-2-{[(1S)-1-[4-(2-tert-butyl-1,1,3-trioxo-2,3-dihydroisothiazol-5-yl)benzyl]-2-oxo-2-(pentylamino)ethyl]amino}-2-oxoethyl)carbamate

Chemical Property:

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Technology Process of tert-butyl ((1S)-1-benzyl-2-{[(1S)-1-[4-(2-tert-butyl-1,1,3-trioxo-2,3-dihydroisothiazol-5-yl)benzyl]-2-oxo-2-(pentylamino)ethyl]amino}-2-oxoethyl)carbamate

There total 6 articles about tert-butyl ((1S)-1-benzyl-2-{[(1S)-1-[4-(2-tert-butyl-1,1,3-trioxo-2,3-dihydroisothiazol-5-yl)benzyl]-2-oxo-2-(pentylamino)ethyl]amino}-2-oxoethyl)carbamate 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: 85.0%

(2S)-2-amino-3-[4-(2-tert-butyl-1,1,3-trioxo-2,3-dihydroisothiazol-5-yl)phenyl]-N-pentylpropanamide monohydrochloride + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → tert-butyl ((1S)-1-benzyl-2-{[(1S)-1-[4-(2-tert-butyl-1,1,3-trioxo-2,3-dihydroisothiazol-5-yl)benzyl]-2-oxo-2-(pentylamino)ethyl]amino}-2-oxoethyl)carbamate (910606-87-0)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; for 16h;

DOI:10.1016/j.bmc.2006.05.032

Reference yield:

2-tert-butyl-5-chloro-1,1-dioxo-1,2-dihydro-1λ6-isothiazol-3-one (850314-47-5) → tert-butyl ((1S)-1-benzyl-2-{[(1S)-1-[4-(2-tert-butyl-1,1,3-trioxo-2,3-dihydroisothiazol-5-yl)benzyl]-2-oxo-2-(pentylamino)ethyl]amino}-2-oxoethyl)carbamate (910606-87-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / K₂CO₃ / PdCl₂(dppf)*CH₂Cl₂ / 1,2-dimethoxy-ethane / 24 h / 80 °C

2: 100 percent / hydrochloric acid / dioxane / 16 h

3: 85 percent / ethyldiisopropylamine; 1-hydroxy-7-azabenzotriazole; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH₂Cl₂; dimethylformamide / 16 h

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; 1: Suzuki coupling;

DOI:10.1016/j.bmc.2006.05.032

Reference yield:

Nα-(tert-butoxycarbonyl)-4-(dihydroxyboryl)-N-pentyl-L-phenylalaninamide (850314-48-6) → tert-butyl ((1S)-1-benzyl-2-{[(1S)-1-[4-(2-tert-butyl-1,1,3-trioxo-2,3-dihydroisothiazol-5-yl)benzyl]-2-oxo-2-(pentylamino)ethyl]amino}-2-oxoethyl)carbamate (910606-87-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / K₂CO₃ / PdCl₂(dppf)*CH₂Cl₂ / 1,2-dimethoxy-ethane / 24 h / 80 °C

2: 100 percent / hydrochloric acid / dioxane / 16 h

3: 85 percent / ethyldiisopropylamine; 1-hydroxy-7-azabenzotriazole; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH₂Cl₂; dimethylformamide / 16 h

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; 1: Suzuki coupling;

DOI:10.1016/j.bmc.2006.05.032

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

2-tert-butyl-5-chloro-1,1-dioxo-1,2-dihydro-1λ⁶-isothiazol-3-one

Nα-(tert-butoxycarbonyl)-4-(dihydroxyboryl)-N-pentyl-L-phenylalaninamide

tert-butyl [(1S)-1-[4-(2-tert-butyl-1,1,3-trioxo-2,3-dihydroisothiazol-5-yl)benzyl]-2-oxo-2-(pentylamino)ethyl]carbamate

Downstream raw materials:

(2S)-3-[4-(2-tert-butyl-1,1,3-trioxo-2,3-dihydroisothiazol-5-yl)phenyl]-2-[((2S)-2-{[(4-methoxyphenyl)acetyl]amino}-3-phenylpropanoyl)amino]-N-pentylpropanamide

3-[4-(2-tert-butyl-1,1,3-trioxo-1λ⁶-isothiazolidin-5-yl)-phenyl]-2-{2-[2-(4-methoxy-phenyl)-acetylamino]-3-phenyl-propionylamino}-N-pentyl-propionamide

3-[4-(2-tert-butyl-1,1,3-trioxo-1λ⁶-isothiazolidin-5-yl)-phenyl]-2-{2-[2-(4-methoxy-phenyl)-acetylamino]-3-phenyl-propionylamino}-N-pentyl-propionamide

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