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

Base Information

• Chemical Name: <1S-(1α,2α,3α,4α)>-2-<<3-<4-<<(4-cyclohexylbutyl)amino>thiomethyl>-2-oxazolyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid methyl ester
• CAS No.: 142663-78-3
• Molecular Formula: C₃₁H₄₂N₂O₄S
• Molecular Weight: 538.751
• Mol file: 142663-78-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 24 articles about <1S-(1α,2α,3α,4α)>-2-<<3-<4-<<(4-cyclohexylbutyl)amino>thiomethyl>-2-oxazolyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic 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: 84.0%

<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) → <1S-(1α,2α,3α,4α)>-2-<<3-<4-<<(4-cyclohexylbutyl)amino>thiomethyl>-2-oxazolyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid methyl ester (142663-78-3)

Guidance literature:

With pyridine; diphosphorus pentasulfide; In dichloromethane; for 16h; Heating;

DOI:10.1021/jm00062a013

Reference yield:

7-oxabicyclo<2.2.1>heptane tetrahydrofuranol (404575-34-4) → <1S-(1α,2α,3α,4α)>-2-<<3-<4-<<(4-cyclohexylbutyl)amino>thiomethyl>-2-oxazolyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid methyl ester (142663-78-3)

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: 84 percent / phosphorus pentasulfide, pyridine / CH₂Cl₂ / 16 h / Heating

With pyridine; chromium(VI) oxide; hydrogenchloride; tetrachloromethane; diphosphorus pentasulfide; 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

Reference yield:

3-[2-((1S,2R,3R,4R)-3-Hydroxymethyl-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl)-phenyl]-propionic acid (142758-00-7) → <1S-(1α,2α,3α,4α)>-2-<<3-<4-<<(4-cyclohexylbutyl)amino>thiomethyl>-2-oxazolyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid methyl ester (142663-78-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 68.5 percent / HCl / 15 h / Ambient temperature

2: 82 percent / CrO₃, H₂SO₄ / acetone / 0.67 h / 25 °C

3: 1.) 1-hydroxybenzotriazole, Et₃N, 2.) dicyclohexylcarbodiimide / 1.) THF, 0 deg C, 5 min, 2.) THF, from 0 deg C to RT, 20 h

4: 77 percent / Ph₃P, diisopropylethylamine, CCl₄ / acetonitrile; CH₂Cl₂ / 2.5 h / Ambient temperature

5: 65 percent / CuBr₂, DBU / ethyl acetate; CHCl₃ / 22 h

6: 94 percent / H₂ / 20percent Pd(OH)2-C / ethyl acetate / 3 h / 760 Torr

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

8: Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

9: 84 percent / phosphorus pentasulfide, pyridine / CH₂Cl₂ / 16 h / Heating

With pyridine; chromium(VI) oxide; hydrogenchloride; tetrachloromethane; diphosphorus pentasulfide; 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 dichloromethane; chloroform; 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