{4-[(5-cyano-3-methoxy-benzofuran-2-carbonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl ester

Base Information

Chemical Name:{4-[(5-cyano-3-methoxy-benzofuran-2-carbonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl ester
CAS No.:174774-87-9
Molecular Formula:C₂₃H₂₈N₂O₆
Molecular Weight:428.485
Hs Code.:

{4-[(5-cyano-3-methoxy-benzofuran-2-carbonyl)-amino]-cyclohexyloxy}-acetic acid <i>tert</i>-butyl ester

Synonyms:{4-[(5-cyano-3-methoxy-benzofuran-2-carbonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl ester

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Chemical Property of {4-[(5-cyano-3-methoxy-benzofuran-2-carbonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl ester

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Technology Process of {4-[(5-cyano-3-methoxy-benzofuran-2-carbonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl ester

There total 9 articles about {4-[(5-cyano-3-methoxy-benzofuran-2-carbonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl 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: 73.0%

: 174774-86-8
5-cyano-3-methoxybenzofuran-2-carboxylic acid

: 160132-94-5
tert-butyl trans-(4-aminocyclohexyloxy)acetate

: 174774-87-9
{4-[(5-cyano-3-methoxy-benzofuran-2-carbonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl ester

Guidance literature:: With benzotriazol-1-ol; In N,N-dimethyl-formamide; at 20 ℃; for 18h;
DOI:10.1248/cpb.47.1694

Reference yield:

: 5292-43-3
bromoacetic acid tert-butyl ester

: 174774-87-9
{4-[(5-cyano-3-methoxy-benzofuran-2-carbonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 45 percent / n-Bu₄NHSO₄; aq. NaOH / toluene / 15 h / 20 °C

2: 57 percent / aq. NH₄Cl / 2-methyl-propan-2-ol / 2 h / Heating

3: 73 percent / HOBt; EDI / dimethylformamide / 18 h / 20 °C

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; ammonium chloride; benzotriazol-1-ol; In N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1: Substitution / 2: deprotection / 3: coupling;
DOI:10.1248/cpb.47.1694

Reference yield:

: 4068-76-2
5-bromo-2-hydroxy-benzoic acid methyl ester

: 174774-87-9
{4-[(5-cyano-3-methoxy-benzofuran-2-carbonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 15 percent / copper sulfate / 1-methyl-pyrrolidin-2-one / 2 h / Heating

2: K₂CO₃ / dimethylformamide / 18 h / 20 °C

3: 100 percent / Na / ethanol / 0.75 h / 20 °C

4: 91 percent / K₂CO₃ / acetone / 1.5 h / Heating

5: 82 percent / KOH / methanol / 0.75 h / Heating

6: 73 percent / HOBt; EDI / dimethylformamide / 18 h / 20 °C

With potassium hydroxide; copper(I) sulfate; sodium; potassium carbonate; benzotriazol-1-ol; copper(II) sulfate; In 1-methyl-pyrrolidin-2-one; methanol; ethanol; N,N-dimethyl-formamide; acetone; 1: Substitution / 2: Etherification / 3: Cyclization / 4: Methylation / 5: hydrolysis / 6: coupling;
DOI:10.1248/cpb.47.1694