4-(2-{(1S,2R,3S,4R)-3-[(S)-1-(4-Cyclohexyl-butylcarbamoyl)-2-hydroxy-ethylcarbamoyl]-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl}-phenyl)-butyric acid methyl ester

Base Information

• Chemical Name: 4-(2-{(1S,2R,3S,4R)-3-[(S)-1-(4-Cyclohexyl-butylcarbamoyl)-2-hydroxy-ethylcarbamoyl]-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl}-phenyl)-butyric acid methyl ester
• CAS No.: 1026878-22-7
• Molecular Formula: C₃₂H₄₈N₂O₆
• Molecular Weight: 556.743

Synonyms:4-(2-{(1S,2R,3S,4R)-3-[(S)-1-(4-Cyclohexyl-butylcarbamoyl)-2-hydroxy-ethylcarbamoyl]-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl}-phenyl)-butyric acid methyl ester

Chemical Property of 4-(2-{(1S,2R,3S,4R)-3-[(S)-1-(4-Cyclohexyl-butylcarbamoyl)-2-hydroxy-ethylcarbamoyl]-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl}-phenyl)-butyric acid methyl ester

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Technology Process of 4-(2-{(1S,2R,3S,4R)-3-[(S)-1-(4-Cyclohexyl-butylcarbamoyl)-2-hydroxy-ethylcarbamoyl]-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl}-phenyl)-butyric acid methyl ester

There total 4 articles about 4-(2-{(1S,2R,3S,4R)-3-[(S)-1-(4-Cyclohexyl-butylcarbamoyl)-2-hydroxy-ethylcarbamoyl]-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl}-phenyl)-butyric 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:

N-(4-cyclohexylbutyl)-L-serinamide (130776-17-9) + (1R,2S,3R,4S)-3-[2-(3-Methoxycarbonyl-propyl)-benzyl]-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid (149079-90-3) → 4-(2-{(1S,2R,3S,4R)-3-[(S)-1-(4-Cyclohexyl-butylcarbamoyl)-2-hydroxy-ethylcarbamoyl]-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl}-phenyl)-butyric acid methyl ester (1026878-22-7)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 0 - 25 ℃;

DOI:10.1021/jm00062a013

Reference yield:

4-cyclohexyl-1-butanamine hydrochloride (91342-30-2) → 4-(2-{(1S,2R,3S,4R)-3-[(S)-1-(4-Cyclohexyl-butylcarbamoyl)-2-hydroxy-ethylcarbamoyl]-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl}-phenyl)-butyric acid methyl ester (1026878-22-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1-hydroxybenzotriazole, 4-methylmorpholine, ethyl (3-(dimethylamino)propyl)carbodiimide hydrochloride / dimethylformamide / Ambient temperature

2: 12.7 g / trifluoroacetic acid / CH₂Cl₂ / 4 h / Ambient temperature

3: 1-hydroxybenzotriazole, Et₃N, ethyl (3-(dimethylamino)propyl)carbodiimide hydrochloride / dimethylformamide / 0 - 25 °C

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00062a013

Reference yield:

<1S-1α,2α,3α,4α>-2-<<3-(hydroxymethyl)-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenebutanoic acid, methyl ester (135613-44-4) → 4-(2-{(1S,2R,3S,4R)-3-[(S)-1-(4-Cyclohexyl-butylcarbamoyl)-2-hydroxy-ethylcarbamoyl]-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl}-phenyl)-butyric acid methyl ester (1026878-22-7)

Guidance literature:

Multi-step reaction with 2 steps

1: CrO₃, H₂SO₄ / acetone / 25 °C

2: 1-hydroxybenzotriazole, Et₃N, ethyl (3-(dimethylamino)propyl)carbodiimide hydrochloride / dimethylformamide / 0 - 25 °C

With chromium(VI) oxide; sulfuric acid; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00062a013

upstream raw materials:

N-(4-cyclohexylbutyl)-L-serinamide

(1R,2S,3R,4S)-3-[2-(3-Methoxycarbonyl-propyl)-benzyl]-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid

4-cyclohexyl-1-butanamine hydrochloride

<1S-1α,2α,3α,4α>-2-<<3-(hydroxymethyl)-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenebutanoic acid, methyl ester

Downstream raw materials:

4-(2-{(1S,2R,3S,4R)-3-[4-(4-Cyclohexyl-butylcarbamoyl)-4,5-dihydro-oxazol-2-yl]-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl}-phenyl)-butyric acid methyl ester

4-(2-{(1S,2R,3S,4R)-3-[4-(4-Cyclohexyl-butylcarbamoyl)-oxazol-2-yl]-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl}-phenyl)-butyric acid methyl ester

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