4-[(2-{(4S)-4-[(1E,3S)-4-(1,1'-biphenyl-3-yl)-3-hydroxybut-1-enyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)sulfanyl]butanoic acid

Base Information

• Chemical Name: 4-[(2-{(4S)-4-[(1E,3S)-4-(1,1'-biphenyl-3-yl)-3-hydroxybut-1-enyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)sulfanyl]butanoic acid
• CAS No.: 729611-34-1
• Molecular Formula: C₂₅H₂₉NO₅S
• Molecular Weight: 455.575
• Mol file: 729611-34-1.mol

Synonyms:4-[(2-{(4S)-4-[(1E,3S)-4-(1,1'-biphenyl-3-yl)-3-hydroxybut-1-enyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)sulfanyl]butanoic acid

Chemical Property of 4-[(2-{(4S)-4-[(1E,3S)-4-(1,1'-biphenyl-3-yl)-3-hydroxybut-1-enyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)sulfanyl]butanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[(2-{(4S)-4-[(1E,3S)-4-(1,1'-biphenyl-3-yl)-3-hydroxybut-1-enyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)sulfanyl]butanoic acid

There total 14 articles about 4-[(2-{(4S)-4-[(1E,3S)-4-(1,1'-biphenyl-3-yl)-3-hydroxybut-1-enyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)sulfanyl]butanoic 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:

(15α,13E)-9-oxo-15-hydroxy-16-(3-phenylphenyl)-17,18,19,20-tetranol-5-thia-8-aza-10-oxaprost-13-enoic acid-n-butylester → 4-[(2-{(4S)-4-[(1E,3S)-4-(1,1'-biphenyl-3-yl)-3-hydroxybut-1-enyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)sulfanyl]butanoic acid (729611-34-1)

Guidance literature:

(15α,13E)-9-oxo-15-hydroxy-16-(3-phenylphenyl)-17,18,19,20-tetranol-5-thia-8-aza-10-oxaprost-13-enoic acid-n-butylester; With methanol; sodium hydroxide; water;

With hydrogenchloride;

Reference yield:

ethyl {(4S)-4-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}acetate (597577-80-5) → 4-[(2-{(4S)-4-[(1E,3S)-4-(1,1'-biphenyl-3-yl)-3-hydroxybut-1-enyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)sulfanyl]butanoic acid (729611-34-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 3 h / 0 - 20 °C / Inert atmosphere

2.1: triethylamine / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

3.1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 50 °C

4.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere

5.1: methyl-phenyl-thioether; trifluoroacetic acid / 10 h / 50 °C / Inert atmosphere

6.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / ethyl acetate / 0.5 h / 0 °C

7.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 - 20 °C / Inert atmosphere

7.2: 0.33 h / 0 - 20 °C

8.1: borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 1.08 h / 20 °C / Inert atmosphere

9.1: sodium hydroxide / 1,2-dimethoxyethane; ethanol / 16 h / 20 °C

9.2: Cooling

With sodium tetrahydroborate; borane-THF; methyl-phenyl-thioether; potassium tert-butylate; sulfur trioxide pyridine complex; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; ethyl acetate; N,N-dimethyl-formamide; toluene; mineral oil; 7.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.bmc.2011.12.009

Reference yield:

(4S)-4-[(benzyloxy)methyl]-3-(2-hydroxyethyl)-1,3-oxazolidin-2-one (1357177-74-2) → 4-[(2-{(4S)-4-[(1E,3S)-4-(1,1'-biphenyl-3-yl)-3-hydroxybut-1-enyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)sulfanyl]butanoic acid (729611-34-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: triethylamine / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

2.1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 50 °C

3.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere

4.1: methyl-phenyl-thioether; trifluoroacetic acid / 10 h / 50 °C / Inert atmosphere

5.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / ethyl acetate / 0.5 h / 0 °C

6.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 - 20 °C / Inert atmosphere

6.2: 0.33 h / 0 - 20 °C

7.1: borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 1.08 h / 20 °C / Inert atmosphere

8.1: sodium hydroxide / 1,2-dimethoxyethane; ethanol / 16 h / 20 °C

8.2: Cooling

With borane-THF; methyl-phenyl-thioether; potassium tert-butylate; sulfur trioxide pyridine complex; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; ethyl acetate; N,N-dimethyl-formamide; toluene; mineral oil; 6.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.bmc.2011.12.009

upstream raw materials:

ethyl {(4S)-4-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}acetate

(4S)-4-[(benzyloxy)methyl]-3-(2-hydroxyethyl)-1,3-oxazolidin-2-one

S-(2-{(4S)-4-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl) ethanethioate

butyl 4-({2-[(4S)-4-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}thio)butanoate

Refernces

• 1、 -. "8-AZAPROSTAGLANDIN DERIVATIVES AND MEDICINAL USES THEREOF". Page/Page column 44-45. . Retrieved 2010/02/14.