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

Base Information

• Chemical Name: methyl trans-4-[1-[[7-fluoro-2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl]acetyl]-(5R)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate
• CAS No.: 441717-53-9
• Molecular Formula: C₃₁H₃₇F₂N₃O₆
• Molecular Weight: 585.648

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

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

Chemical Property:

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

There total 8 articles about methyl trans-4-[1-[[7-fluoro-2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl]acetyl]-(5R)-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: 99.0%

[2-(5-fluoro-2-methylphenylamino)-7-fluoro-6-benzoxazolyl]acetic acid (441714-46-1) + methyl trans-4-[(5R)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate (441717-51-7) → methyl trans-4-[1-[[7-fluoro-2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl]acetyl]-(5R)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate (441717-53-9)

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:

(2S)-Benzyloxymethyl-1-tert-butoxycarbonyl-(5R)-methoxymethylpyrrolidine (441717-46-0) → methyl trans-4-[1-[[7-fluoro-2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl]acetyl]-(5R)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate (441717-53-9)

Guidance literature:

Multi-step reaction with 9 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 15 h

2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 10 h / Reflux

3: trifluoroacetic acid / dichloromethane / 17 h / 20 °C

4: Rh/Al₂O₃; hydrogen / methanol / 24 h / 7600.51 Torr

5: sodium hydrogencarbonate / 1,4-dioxane; water / 2 h / 20 °C

6: sodium methylate / methanol / 20 h / Reflux

7: diazomethyl-trimethyl-silane / benzene / 3 h / 20 °C

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

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

With di-isopropyl azodicarboxylate; palladium 10% on activated carbon; Rh/Al₂O₃; hydrogen; sodium methylate; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; trifluoroacetic acid; diazomethyl-trimethyl-silane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene; 2: |Mitsunobu Displacement;

DOI:10.1016/j.bmc.2012.11.003

Reference yield:

methyl trans-4-[1-tert-butoxycarbonyl-(5R)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate (441717-49-3) → methyl trans-4-[1-[[7-fluoro-2-(5-fluoro-2-methylphenylamino)-6-benzoxazolyl]acetyl]-(5R)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate (441717-53-9)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2012.11.003

upstream raw materials:

(2S,5R)-1-tert-butoxycarbonyl-5-hydroxymethyl-2-benzyloxymethyl pyrrolidine

(2S)-Benzyloxymethyl-1-tert-butoxycarbonyl-(5R)-methoxymethylpyrrolidine

1-tert-butoxycarbonyl-(5R)-methoxymethyl-(2S)-pyrrolidinemethanol

methyl 4-[1-tert-butoxycarbonyl-(5R)-methoxymethyl-(2S)-pyrrolidinylmethoxy]benzoate

Downstream raw materials:

C₃₀H₃₅F₂N₃O₆

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