(S)-N-(1S,2R)-<3-<2-<<(1,1-dimethylethyl)amino>carbonyl>phenyl>-2-hydroxy-1-(phenylmethyl)propyl>-2-<(tert-butoxycarbonyl)amino>-3-<(p-chlorophenyl)sulfonyl>propanamide

Base Information

• Chemical Name: (S)-N-(1S,2R)-<3-<2-<<(1,1-dimethylethyl)amino>carbonyl>phenyl>-2-hydroxy-1-(phenylmethyl)propyl>-2-<(tert-butoxycarbonyl)amino>-3-<(p-chlorophenyl)sulfonyl>propanamide
• CAS No.: 172882-72-3
• Molecular Formula: C₃₅H₄₄ClN₃O₇S
• Molecular Weight: 686.269

Synonyms:(S)-N-(1S,2R)-<3-<2-<<(1,1-dimethylethyl)amino>carbonyl>phenyl>-2-hydroxy-1-(phenylmethyl)propyl>-2-<(tert-butoxycarbonyl)amino>-3-<(p-chlorophenyl)sulfonyl>propanamide

Chemical Property of (S)-N-(1S,2R)-<3-<2-<<(1,1-dimethylethyl)amino>carbonyl>phenyl>-2-hydroxy-1-(phenylmethyl)propyl>-2-<(tert-butoxycarbonyl)amino>-3-<(p-chlorophenyl)sulfonyl>propanamide

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Technology Process of (S)-N-(1S,2R)-<3-<2-<<(1,1-dimethylethyl)amino>carbonyl>phenyl>-2-hydroxy-1-(phenylmethyl)propyl>-2-<(tert-butoxycarbonyl)amino>-3-<(p-chlorophenyl)sulfonyl>propanamide

There total 5 articles about (S)-N-(1S,2R)-<3-<2-<<(1,1-dimethylethyl)amino>carbonyl>phenyl>-2-hydroxy-1-(phenylmethyl)propyl>-2-<(tert-butoxycarbonyl)amino>-3-<(p-chlorophenyl)sulfonyl>propanamide 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: 77.0%

[2R-(2R*,3S,)]-N-t-Butyl-2-(3-amino-2-hydroxy-4-phenylbutyl) benzamide (157309-35-8) + (S)-2-<(tert-butoxycarbonyl)amino>-3-<(p-chlorophenyl)sulfonyl>propionic acid (172882-71-2) → (S)-N-(1S,2R)-<3-<2-<<(1,1-dimethylethyl)amino>carbonyl>phenyl>-2-hydroxy-1-(phenylmethyl)propyl>-2-<(tert-butoxycarbonyl)amino>-3-<(p-chlorophenyl)sulfonyl>propanamide (172882-72-3)

Guidance literature:

With 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; In tetrahydrofuran; a) 0 deg C, 2 h, b) RT, overnight;

DOI:10.1021/jm950576c

Reference yield:

methyl N-(tert-butoxycarbonyl)-O-[(4-methylphenyl)sulfonyl]-D-serinate (126645-21-4) → (S)-N-(1S,2R)-<3-<2-<<(1,1-dimethylethyl)amino>carbonyl>phenyl>-2-hydroxy-1-(phenylmethyl)propyl>-2-<(tert-butoxycarbonyl)amino>-3-<(p-chlorophenyl)sulfonyl>propanamide (172882-72-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 20 min, 2.) DMF, 0 deg C, 2 h

2: 0.5 M aq. LiOH / dioxane / 22 h

3: aq. oxone / 0 - 20 °C

4: 77 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide / tetrahydrofuran / a) 0 deg C, 2 h, b) RT, overnight

With Oxone; lithium hydroxide; sodium hydride; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1021/jm950576c

Reference yield:

p-Chlorothiophenol (106-54-7) → (S)-N-(1S,2R)-<3-<2-<<(1,1-dimethylethyl)amino>carbonyl>phenyl>-2-hydroxy-1-(phenylmethyl)propyl>-2-<(tert-butoxycarbonyl)amino>-3-<(p-chlorophenyl)sulfonyl>propanamide (172882-72-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 20 min, 2.) DMF, 0 deg C, 2 h

2: 0.5 M aq. LiOH / dioxane / 22 h

3: aq. oxone / 0 - 20 °C

4: 77 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide / tetrahydrofuran / a) 0 deg C, 2 h, b) RT, overnight

With Oxone; lithium hydroxide; sodium hydride; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1021/jm950576c

upstream raw materials:

[2R-(2R*,3S,)]-N-t-Butyl-2-(3-amino-2-hydroxy-4-phenylbutyl) benzamide

(S)-2-<(tert-butoxycarbonyl)amino>-3-<(p-chlorophenyl)sulfonyl>propionic acid

methyl N-(tert-butoxycarbonyl)-O-[(4-methylphenyl)sulfonyl]-D-serinate

p-Chlorothiophenol

Downstream raw materials:

2-{(2R,3S)-3-[(S)-2-Amino-3-(4-chloro-benzenesulfonyl)-propionylamino]-2-hydroxy-4-phenyl-butyl}-N-tert-butyl-benzamide

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