methyl trans-4-[1-[[7-fluoro-2-(2-methylphenylamino)-6-benzoxazolyl]acetyl]-(5S)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate

Base Information

• Chemical Name: methyl trans-4-[1-[[7-fluoro-2-(2-methylphenylamino)-6-benzoxazolyl]acetyl]-(5S)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate
• CAS No.: 1416961-22-2
• Molecular Formula: C₃₁H₃₈FN₃O₆
• Molecular Weight: 567.658

Synonyms:methyl trans-4-[1-[[7-fluoro-2-(2-methylphenylamino)-6-benzoxazolyl]acetyl]-(5S)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate

Chemical Property of methyl trans-4-[1-[[7-fluoro-2-(2-methylphenylamino)-6-benzoxazolyl]acetyl]-(5S)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate

Chemical Property:

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Technology Process of methyl trans-4-[1-[[7-fluoro-2-(2-methylphenylamino)-6-benzoxazolyl]acetyl]-(5S)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate

There total 7 articles about methyl trans-4-[1-[[7-fluoro-2-(2-methylphenylamino)-6-benzoxazolyl]acetyl]-(5S)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate 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: 91.0%

[7-fluoro-2-(2-methylphenylamino)-6-benzoxazolyl]acetic acid + methyl trans-4-[(5S)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate (441716-92-3) → methyl trans-4-[1-[[7-fluoro-2-(2-methylphenylamino)-6-benzoxazolyl]acetyl]-(5S)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate (1416961-22-2)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1016/j.bmc.2012.11.003

Reference yield:

methyl 4-hydroxylbenzoate (99-76-3,156291-94-0) → methyl trans-4-[1-[[7-fluoro-2-(2-methylphenylamino)-6-benzoxazolyl]acetyl]-(5S)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate (1416961-22-2)

Guidance literature:

Multi-step reaction with 6 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate / 2 h / 60 °C

2: Rh/Al₂O₃; hydrogen / acetic acid; ethanol / 2.5 h / 20 °C / 8?atm

3: sodium methylate / methanol / Reflux

4: diazomethyl-trimethyl-silane / benzene; hexane / 1 h / 20 °C

5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

6: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 2 h / 20 °C

With di-isopropyl azodicarboxylate; Rh/Al₂O₃; hydrogen; sodium methylate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; trifluoroacetic acid; diazomethyl-trimethyl-silane; In methanol; ethanol; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; benzene; 1: |Mitsunobu Displacement;

DOI:10.1016/j.bmc.2012.11.003

Reference yield:

1-tert-butoxycarbonyl-(2S)-hydroxymethyl-(5S)-methoxymethylpyrrolidine (441716-89-8) → methyl trans-4-[1-[[7-fluoro-2-(2-methylphenylamino)-6-benzoxazolyl]acetyl]-(5S)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate (1416961-22-2)

Guidance literature:

Multi-step reaction with 6 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate / 2 h / 60 °C

2: Rh/Al₂O₃; hydrogen / acetic acid; ethanol / 2.5 h / 20 °C / 8?atm

3: sodium methylate / methanol / Reflux

4: diazomethyl-trimethyl-silane / benzene; hexane / 1 h / 20 °C

5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

6: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 2 h / 20 °C

With di-isopropyl azodicarboxylate; Rh/Al₂O₃; hydrogen; sodium methylate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; trifluoroacetic acid; diazomethyl-trimethyl-silane; In methanol; ethanol; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; benzene; 1: |Mitsunobu Displacement;

DOI:10.1016/j.bmc.2012.11.003

upstream raw materials:

methyl 4-hydroxylbenzoate

methyl trans-4-[(5S)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate

1-tert-butoxycarbonyl-(2S)-hydroxymethyl-(5S)-methoxymethylpyrrolidine

(2S,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-hydroxymethylpyrrolidine

Downstream raw materials:

C₃₀H₃₆FN₃O₆

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