[2-({(S)-(3,5-dichloro-4-methoxyphenyl)-[2-(3-hydroxyphenyl)acetylamino]acetyl}methylamino)-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester

Base Information

• Chemical Name: [2-({(S)-(3,5-dichloro-4-methoxyphenyl)-[2-(3-hydroxyphenyl)acetylamino]acetyl}methylamino)-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester
• CAS No.: 193074-12-3
• Molecular Formula: C₃₇H₃₅Cl₂FN₄O₁₀
• Molecular Weight: 785.61

Synonyms:[2-({(S)-(3,5-dichloro-4-methoxyphenyl)-[2-(3-hydroxyphenyl)acetylamino]acetyl}methylamino)-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester

Chemical Property of [2-({(S)-(3,5-dichloro-4-methoxyphenyl)-[2-(3-hydroxyphenyl)acetylamino]acetyl}methylamino)-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester

Chemical Property:

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Technology Process of [2-({(S)-(3,5-dichloro-4-methoxyphenyl)-[2-(3-hydroxyphenyl)acetylamino]acetyl}methylamino)-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester

There total 16 articles about [2-({(S)-(3,5-dichloro-4-methoxyphenyl)-[2-(3-hydroxyphenyl)acetylamino]acetyl}methylamino)-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl 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: 81.0%

m-hydroxyphenylacetic acid (621-37-4) + (R)-[(S)-2-{[(S)-2-Amino-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-(4-methoxy-phenyl)-acetic acid methyl ester (249757-19-5) → [2-({(S)-(3,5-dichloro-4-methoxyphenyl)-[2-(3-hydroxyphenyl)acetylamino]acetyl}methylamino)-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester (193074-12-3)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane;

DOI:10.1016/S0040-4039(97)00938-6

Reference yield:

methyl 4-methoxyphenyl-D-phenylglycinate (78307-39-8) → [2-({(S)-(3,5-dichloro-4-methoxyphenyl)-[2-(3-hydroxyphenyl)acetylamino]acetyl}methylamino)-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester (193074-12-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / HOBT, EDC, NEt₃ / CH₂Cl₂

2: 81 percent / TMSCl, INa / CHCl₃

3: 65 percent / bromotris(pyrrolidino)phosphonium hexafluorophosphate / CH₂Cl₂ / 0 °C

4: 90 percent / TMSCl, INa / CHCl₃

5: 81 percent / HOBT, EDC / CH₂Cl₂

With chloro-trimethyl-silane; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; sodium iodide; In dichloromethane; chloroform;

DOI:10.1016/S0040-4039(97)00938-6

Reference yield:

4-(bromomethyl)-1-fluoro-2-nitrobenzene (15017-52-4) → [2-({(S)-(3,5-dichloro-4-methoxyphenyl)-[2-(3-hydroxyphenyl)acetylamino]acetyl}methylamino)-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester (193074-12-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) n-BuLi, CuCN; 2.) TFA, H₂O / 1.) THF, -20 deg C; 2.) acetonitrile

2: 54 percent / NEt₃ / tetrahydrofuran

3: 83 percent / Ag₂O / dimethylformamide

4: 90 percent / K₂CO₃, H₂O / methanol

5: 92 percent / HOBT, EDC, NEt₃ / CH₂Cl₂

6: 81 percent / TMSCl, INa / CHCl₃

7: 65 percent / bromotris(pyrrolidino)phosphonium hexafluorophosphate / CH₂Cl₂ / 0 °C

8: 90 percent / TMSCl, INa / CHCl₃

9: 81 percent / HOBT, EDC / CH₂Cl₂

With n-butyllithium; chloro-trimethyl-silane; water; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; trifluoroacetic acid; sodium iodide; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(97)00938-6

upstream raw materials:

m-hydroxyphenylacetic acid

(R)-[(S)-2-{[(S)-2-Amino-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-(4-methoxy-phenyl)-acetic acid methyl ester

methyl 4-methoxyphenyl-D-phenylglycinate

4-(bromomethyl)-1-fluoro-2-nitrobenzene

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