(S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid

Base Information

• Chemical Name: (S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid
• CAS No.: 192328-71-5
• Molecular Formula: C₁₈H₂₁FN₄O₈
• Molecular Weight: 440.385

Synonyms:(S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid

Chemical Property of (S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid

Chemical Property:

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Technology Process of (S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid

There total 6 articles about (S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid 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: 99.0%

(S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid methyl ester (192328-70-4) → (S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid (192328-71-5)

Guidance literature:

With lithium hydroxide;

DOI:10.1016/S0960-894X(98)00110-3

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid (192328-71-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent

2: 96 percent / LiOH / 2-methyl-propan-2-ol; H₂O / 0.5 h / 25 °C

3: 64 percent / EDCI

4: 58 percent / tetrahydrofuran

5: 98 percent / LiOH / 2-methyl-propan-2-ol; H₂O / 0.75 h / 0 °C

With lithium hydroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; water; tert-butyl alcohol;

DOI:10.1021/jo970560p

Reference yield:

(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionic acid (174146-55-5) → (S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid (192328-71-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / EDCI

2: 58 percent / tetrahydrofuran

3: 98 percent / LiOH / 2-methyl-propan-2-ol; H₂O / 0.75 h / 0 °C

With lithium hydroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; water; tert-butyl alcohol;

DOI:10.1021/jo970560p

upstream raw materials:

(S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionic acid methyl ester

di-tert-butyl dicarbonate

(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionic acid

(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionic acid methyl ester

Downstream raw materials:

(R)-{(S)-2-[(2R,3R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionylamino]-3-cyano-propionylamino}-(3,5-dihydroxy-4-methoxy-phenyl)-acetic acid tert-butyl ester

C₅₂H₆₀BrClFN₇O₁₆Si

[(1R,2R)-1-{(S)-2-Cyano-1-[(R)-1-(3,5-dihydroxy-4-methoxy-phenyl)-2-hydroxy-ethylcarbamoyl]-ethylcarbamoyl}-2-(4-fluoro-3-nitro-phenyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester

[(1R,2R)-1-((S)-2-Cyano-1-{[(S)-(3,5-dihydroxy-4-methoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-ethylcarbamoyl)-2-(4-fluoro-3-nitro-phenyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester

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