5-(3-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}propyl)thiophene-2-carboxylic acid

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Chemical Name:5-(3-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}propyl)thiophene-2-carboxylic acid
CAS No.:494222-13-8
Molecular Formula:C₂₃H₂₇NO₄S
Molecular Weight:413.538
Hs Code.:

Synonyms:5-(3-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}propyl)thiophene-2-carboxylic acid

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Chemical Property of 5-(3-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}propyl)thiophene-2-carboxylic acid

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Technology Process of 5-(3-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}propyl)thiophene-2-carboxylic acid

There total 8 articles about 5-(3-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}propyl)thiophene-2-carboxylic 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:

: 494224-32-7
(15α,13E)-9-oxo-15-hydroxy-16-(3-methylphenyl)-1,5-(2,5-interthienylene)-2,3,4,17,18,19,20-heptanor-8-azaprost-13-enoic acid methyl ester

: 494222-13-8
5-(3-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}propyl)thiophene-2-carboxylic acid

Guidance literature:: (15α,13E)-9-oxo-15-hydroxy-16-(3-methylphenyl)-1,5-(2,5-interthienylene)-2,3,4,17,18,19,20-heptanor-8-azaprost-13-enoic acid methyl ester; With sodium hydroxide; In 1,2-dimethoxyethane; at 20 ℃; for 2h;

With hydrogenchloride; In 1,2-dimethoxyethane; water;
DOI:10.1016/j.bmc.2012.02.018

Reference yield:

: 431989-55-8
methyl 5-{3-[(2R)-2-(hydroxymethyl)-5-oxo-1-pyrrolidinyl]propyl}-2-thiophenecarboxylate

: 494222-13-8
5-(3-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}propyl)thiophene-2-carboxylic acid

Guidance literature:: Multi-step reaction with 3 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: 1 h / 0 - 20 °C

3.1: sodium hydroxide / 1,2-dimethoxyethane / 2 h / 20 °C

With sulfur trioxide pyridine complex; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; ethyl acetate; mineral oil; 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.bmc.2012.02.018

Reference yield:

: 431990-33-9
methyl 5-{3-[(2R)-2-({tert-butyldimethylsilyloxy}methyl)-5-oxo-1-pyrrolidinyl]propyl}-2-thiophenecarboxylate

: 494222-13-8
5-(3-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}propyl)thiophene-2-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

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

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

3.2: 1 h / 0 - 20 °C

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

With tetrabutyl ammonium fluoride; sulfur trioxide pyridine complex; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; ethyl acetate; mineral oil; 3.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.bmc.2012.02.018