4-[(2-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-fluorophenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)sulfanyl]butanoic acid

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Chemical Name:4-[(2-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-fluorophenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)sulfanyl]butanoic acid
CAS No.:494222-29-6
Molecular Formula:C₂₀H₂₆FNO₄S
Molecular Weight:395.495
Hs Code.:

Synonyms:4-[(2-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-fluorophenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)sulfanyl]butanoic acid

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Chemical Property of 4-[(2-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-fluorophenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)sulfanyl]butanoic acid

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Technology Process of 4-[(2-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-fluorophenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)sulfanyl]butanoic acid

There total 8 articles about 4-[(2-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-fluorophenyl)but-1-enyl]-5-oxopyrrolidin-1-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: 92.0%

: 1365392-22-8
C₂₁H₂₈FNO₄S

: 494222-29-6
4-[(2-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-fluorophenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)sulfanyl]butanoic acid

Guidance literature:: With water; sodium hydroxide; In 1,2-dimethoxyethane; at 20 ℃; for 10h;
DOI:10.1248/cpb.59.1523

Reference yield:

: 946402-22-8
N-methoxy-N-methyl-2-(3-fluorophenyl)acetamide

: 494222-29-6
4-[(2-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-fluorophenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)sulfanyl]butanoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / hexane; toluene / 1 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 °C / Inert atmosphere

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

2.2: 2 h / 0 °C / Inert atmosphere

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

4.1: water; sodium hydroxide / 1,2-dimethoxyethane / 10 h / 20 °C

With n-butyllithium; borane-THF; water; sodium hydride; sodium hydroxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; toluene; mineral oil; 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1248/cpb.59.1523

Reference yield:

: 492471-45-1
9-oxo-13-hydroxy-14,15,16,17,18,19,20-heptanor-5-thia-8-azaprostanoic acid methyl ester

: 494222-29-6
4-[(2-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-fluorophenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)sulfanyl]butanoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / ethyl acetate / 0.33 h / 0 °C / Inert atmosphere

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

2.2: 2 h / 0 °C / Inert atmosphere

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

4.1: water; sodium hydroxide / 1,2-dimethoxyethane / 10 h / 20 °C

With borane-THF; water; sulfur trioxide pyridine complex; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; sodium hydroxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; 1,2-dimethoxyethane; ethyl acetate; toluene; mineral oil; 1.1: Parikh-Doering oxidation / 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1248/cpb.59.1523