[1S-(1α,2α,3α,4α)]-2-[[3-[4-[[[4-(4-hydroxyphenyl)butyl]amino]carbonyl]-2-oxazolyl]-7-oxabicyclo[2.2.1]hept-2-yl]methyl]benzenepropanoic acid

Base Information

Chemical Name:[1S-(1α,2α,3α,4α)]-2-[[3-[4-[[[4-(4-hydroxyphenyl)butyl]amino]carbonyl]-2-oxazolyl]-7-oxabicyclo[2.2.1]hept-2-yl]methyl]benzenepropanoic acid
CAS No.:149117-78-2
Molecular Formula:C₃₀H₃₄N₂O₆
Molecular Weight:518.61
Hs Code.:

Synonyms:[1S-(1α,2α,3α,4α)]-2-[[3-[4-[[[4-(4-hydroxyphenyl)butyl]amino]carbonyl]-2-oxazolyl]-7-oxabicyclo[2.2.1]hept-2-yl]methyl]benzenepropanoic acid

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of [1S-(1α,2α,3α,4α)]-2-[[3-[4-[[[4-(4-hydroxyphenyl)butyl]amino]carbonyl]-2-oxazolyl]-7-oxabicyclo[2.2.1]hept-2-yl]methyl]benzenepropanoic acid

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of [1S-(1α,2α,3α,4α)]-2-[[3-[4-[[[4-(4-hydroxyphenyl)butyl]amino]carbonyl]-2-oxazolyl]-7-oxabicyclo[2.2.1]hept-2-yl]methyl]benzenepropanoic acid

There total 16 articles about [1S-(1α,2α,3α,4α)]-2-[[3-[4-[[[4-(4-hydroxyphenyl)butyl]amino]carbonyl]-2-oxazolyl]-7-oxabicyclo[2.2.1]hept-2-yl]methyl]benzenepropanoic acid 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:

: [1S(1α,2α,3α,4α)]-2-[[3-[4-[[[4-(4Phenylmethoxyphenyl)butyl]amino]carbonyl]-2-oxazolyl]-7-oxabicyclo[2.2.1]hept-2-yl]methyl]benzenepropanoic acid

: 149117-78-2
[1S-(1α,2α,3α,4α)]-2-[[3-[4-[[[4-(4-hydroxyphenyl)butyl]amino]carbonyl]-2-oxazolyl]-7-oxabicyclo[2.2.1]hept-2-yl]methyl]benzenepropanoic acid

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate; under 760 Torr; Yield given;
DOI:10.1021/jm00062a013

Reference yield:

: 404575-34-4
7-oxabicyclo<2.2.1>heptane tetrahydrofuranol

: 149117-78-2
[1S-(1α,2α,3α,4α)]-2-[[3-[4-[[[4-(4-hydroxyphenyl)butyl]amino]carbonyl]-2-oxazolyl]-7-oxabicyclo[2.2.1]hept-2-yl]methyl]benzenepropanoic acid

Guidance literature:: Multi-step reaction with 15 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: LiOH / tetrahydrofuran; H₂O / 2 h / Ambient temperature

15: H₂ / 10percent Pd-C / methanol; ethyl acetate / 760 Torr

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 on activated charcoal; palladium hydroxide - carbon; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; acetic acid; ethyl acetate; acetone; acetonitrile;
DOI:10.1021/jm00062a013

Reference yield:

: 142758-00-7
3-[2-((1S,2R,3R,4R)-3-Hydroxymethyl-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl)-phenyl]-propionic acid

: 149117-78-2
[1S-(1α,2α,3α,4α)]-2-[[3-[4-[[[4-(4-hydroxyphenyl)butyl]amino]carbonyl]-2-oxazolyl]-7-oxabicyclo[2.2.1]hept-2-yl]methyl]benzenepropanoic acid

Guidance literature:: Multi-step reaction with 10 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: LiOH / tetrahydrofuran; H₂O / 2 h / Ambient temperature

10: H₂ / 10percent Pd-C / methanol; ethyl acetate / 760 Torr

With chromium(VI) oxide; hydrogenchloride; 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 on activated charcoal; palladium hydroxide - carbon; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; ethyl acetate; acetone; acetonitrile;
DOI:10.1021/jm00062a013