Benzenepropanoic acid,2-[[(1S,2R,3S,4R)-3-[4- [[(4-cyclohexylbutyl)amino]carbonyl]-2-oxazolyl]- 7-oxabicyclo[2.2.1]hept-2-yl]methyl]-

Base Information

• Chemical Name: Benzenepropanoic acid,2-[[(1S,2R,3S,4R)-3-[4- [[(4-cyclohexylbutyl)amino]carbonyl]-2-oxazolyl]- 7-oxabicyclo[2.2.1]hept-2-yl]methyl]-
• CAS No.: 139067-88-2
• Molecular Formula: C₃₀H₄₀N₂O₅
• Molecular Weight: 508.658
• Mol file: 139067-88-2.mol

Synonyms:

Chemical Property of Benzenepropanoic acid,2-[[(1S,2R,3S,4R)-3-[4- [[(4-cyclohexylbutyl)amino]carbonyl]-2-oxazolyl]- 7-oxabicyclo[2.2.1]hept-2-yl]methyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzenepropanoic acid,2-[[(1S,2R,3S,4R)-3-[4- [[(4-cyclohexylbutyl)amino]carbonyl]-2-oxazolyl]- 7-oxabicyclo[2.2.1]hept-2-yl]methyl]-

There total 24 articles about Benzenepropanoic acid,2-[[(1S,2R,3S,4R)-3-[4- [[(4-cyclohexylbutyl)amino]carbonyl]-2-oxazolyl]- 7-oxabicyclo[2.2.1]hept-2-yl]methyl]- 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: 97.0%

<1S-(1α,2α,3α,4α)>-2-<<3-<4-<<(4-cyclohexylbutyl)amino>carbonyl>-2-oxazolyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid methyl ester (142663-83-0) → SQ 33961 (139067-88-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; for 2h; Ambient temperature;

DOI:10.1021/jm00062a013

Reference yield:

<1S-1α,2α,3α,4α>-2-<<3-(hydroxymethyl)-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid, methyl ester (135682-53-0) → SQ 33961 (139067-88-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 82 percent / CrO₃, H₂SO₄ / acetone / 0.67 h / 25 °C

2: 1.) 1-hydroxybenzotriazole, Et₃N, 2.) dicyclohexylcarbodiimide / 1.) THF, 0 deg C, 5 min, 2.) THF, from 0 deg C to RT, 20 h

3: 77 percent / Ph₃P, diisopropylethylamine, CCl₄ / acetonitrile; CH₂Cl₂ / 2.5 h / Ambient temperature

4: 65 percent / CuBr₂, DBU / ethyl acetate; CHCl₃ / 22 h

5: 94 percent / H₂ / 20percent Pd(OH)2-C / ethyl acetate / 3 h / 760 Torr

6: oxalyl chloride, DMF / CH₂Cl₂ / 0.67 h / Ambient temperature

7: Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

8: 97 percent / LiOH / tetrahydrofuran; H₂O / 2 h / Ambient temperature

With chromium(VI) oxide; tetrachloromethane; lithium hydroxide; oxalyl dichloride; sulfuric acid; hydrogen; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; dicyclohexyl-carbodiimide; triphenylphosphine; copper(ll) bromide; palladium hydroxide - carbon; In tetrahydrofuran; dichloromethane; chloroform; water; ethyl acetate; acetone; acetonitrile;

DOI:10.1021/jm00062a013

Reference yield:

7-oxabicyclo<2.2.1>heptane tetrahydrofuranol (404575-34-4) → SQ 33961 (139067-88-2)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) EtMgBr / 1.) THF, 0 deg C, 1 h, 2.) THF, 25 deg C, 6 days

2: H₂ / 20percent Pd(OH)2-C / acetic acid / 24 h / 25 °C / 760 Torr

3: pyridine / 16 h / 25 °C

4: CrO₃/H₂SO₄ / acetone / 0.75 h

5: NaOH / tetrahydrofuran; H₂O / 25 °C

6: 68.5 percent / HCl / 15 h / Ambient temperature

7: 82 percent / CrO₃, H₂SO₄ / acetone / 0.67 h / 25 °C

8: 1.) 1-hydroxybenzotriazole, Et₃N, 2.) dicyclohexylcarbodiimide / 1.) THF, 0 deg C, 5 min, 2.) THF, from 0 deg C to RT, 20 h

9: 77 percent / Ph₃P, diisopropylethylamine, CCl₄ / acetonitrile; CH₂Cl₂ / 2.5 h / Ambient temperature

10: 65 percent / CuBr₂, DBU / ethyl acetate; CHCl₃ / 22 h

11: 94 percent / H₂ / 20percent Pd(OH)2-C / ethyl acetate / 3 h / 760 Torr

12: oxalyl chloride, DMF / CH₂Cl₂ / 0.67 h / Ambient temperature

13: Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

14: 97 percent / LiOH / tetrahydrofuran; H₂O / 2 h / Ambient temperature

With pyridine; chromium(VI) oxide; hydrogenchloride; tetrachloromethane; lithium hydroxide; sodium hydroxide; oxalyl dichloride; sulfuric acid; ethylmagnesium bromide; hydrogen; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; dicyclohexyl-carbodiimide; triphenylphosphine; copper(ll) bromide; palladium hydroxide - carbon; In tetrahydrofuran; dichloromethane; chloroform; water; acetic acid; ethyl acetate; acetone; acetonitrile;

DOI:10.1021/jm00062a013

upstream raw materials:

<1S-(1α,2α,3α,4α)>-2-<<3-<4-<<(4-cyclohexylbutyl)amino>carbonyl>-2-oxazolyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid methyl ester

4-cyclohexyl-butylamine

4-phenyl-1-butylamine

4-cyclohexyl-1-butanamine hydrochloride

Downstream raw materials:

<1S-(1α,2α,3α,4α)>-2-<<3-<4-<<(4-cyclohexylbutyl)amino>carbonyl>-2-oxazolyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid ethyl ester

2-{(1R,2S,3R,4S)-3-[2-(2-Benzyloxycarbonyl-ethyl)-benzyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-oxazole-4-carboxylic acid 4-cyclohexyl-butyl ester

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