N-{(3R)-3-[(tert-butylsulfinyl)amino]-3-cyclohexyl-2,2-difluoropropyl}-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-prolinamide

Base Information

Chemical Name:N-{(3R)-3-[(tert-butylsulfinyl)amino]-3-cyclohexyl-2,2-difluoropropyl}-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-prolinamide
CAS No.:479480-58-5
Molecular Formula:C₃₃H₄₃F₂N₃O₄S
Molecular Weight:615.785
Hs Code.:

Synonyms:N-{(3R)-3-[(tert-butylsulfinyl)amino]-3-cyclohexyl-2,2-difluoropropyl}-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-prolinamide

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Chemical Property of N-{(3R)-3-[(tert-butylsulfinyl)amino]-3-cyclohexyl-2,2-difluoropropyl}-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-prolinamide

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Technology Process of N-{(3R)-3-[(tert-butylsulfinyl)amino]-3-cyclohexyl-2,2-difluoropropyl}-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-prolinamide

There total 5 articles about N-{(3R)-3-[(tert-butylsulfinyl)amino]-3-cyclohexyl-2,2-difluoropropyl}-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-prolinamide 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: 92.0%

: 71989-31-6
Fmoc-Pro-OH

: 479480-57-4
N-[(1R)-3-amino-1-cyclohexyl-2,2-difluoropropyl]-2-methylpropane-2-sulfinamide

: 479480-58-5
N-{(3R)-3-[(tert-butylsulfinyl)amino]-3-cyclohexyl-2,2-difluoropropyl}-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-prolinamide

Guidance literature:: With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 18h;
DOI:10.1021/jo0259313

Reference yield:

: 2043-61-0
cyclohexanecarbaldehyde

: 479480-58-5
N-{(3R)-3-[(tert-butylsulfinyl)amino]-3-cyclohexyl-2,2-difluoropropyl}-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-prolinamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: CuSO₄; molecular sieves / CH₂Cl₂

2.1: Zn / tetrahydrofuran

2.2: tetrahydrofuran / 18 h / 20 °C

3.1: 75 percent / NH₃ / diethyl ether / 18 h / 20 °C

4.1: 59 percent / BH₃*DMS / tetrahydrofuran / 5 h / 80 °C

5.1: 92 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxy-7-azabenzotriazole / dimethylformamide / 18 h / 20 °C

With 1-hydroxy-7-aza-benzotriazole; molecular sieve; dimethylsulfide borane complex; ammonia; copper(II) sulfate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; zinc; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0259313

Reference yield:

: 336105-28-3
(R_S,E)-N-(cyclohexylmethylene)-2-methylpropane-2-sulfinamide

: 479480-58-5
N-{(3R)-3-[(tert-butylsulfinyl)amino]-3-cyclohexyl-2,2-difluoropropyl}-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-prolinamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: Zn / tetrahydrofuran

1.2: tetrahydrofuran / 18 h / 20 °C

2.1: 75 percent / NH₃ / diethyl ether / 18 h / 20 °C

3.1: 59 percent / BH₃*DMS / tetrahydrofuran / 5 h / 80 °C

4.1: 92 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxy-7-azabenzotriazole / dimethylformamide / 18 h / 20 °C

With 1-hydroxy-7-aza-benzotriazole; dimethylsulfide borane complex; ammonia; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; zinc; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/jo0259313