7-((2S)-2-{(1E,3S)-3-hydroxy-4-[3-(methoxymethyl)phenyl]but-1-enyl}-5-oxopyrrolidin-1-yl)heptanoic acid

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Chemical Name:7-((2S)-2-{(1E,3S)-3-hydroxy-4-[3-(methoxymethyl)phenyl]but-1-enyl}-5-oxopyrrolidin-1-yl)heptanoic acid
CAS No.:1369916-97-1
Molecular Formula:C₂₃H₃₃NO₅
Molecular Weight:403.519
Hs Code.:

Synonyms:7-((2S)-2-{(1E,3S)-3-hydroxy-4-[3-(methoxymethyl)phenyl]but-1-enyl}-5-oxopyrrolidin-1-yl)heptanoic acid

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Chemical Property of 7-((2S)-2-{(1E,3S)-3-hydroxy-4-[3-(methoxymethyl)phenyl]but-1-enyl}-5-oxopyrrolidin-1-yl)heptanoic acid

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Technology Process of 7-((2S)-2-{(1E,3S)-3-hydroxy-4-[3-(methoxymethyl)phenyl]but-1-enyl}-5-oxopyrrolidin-1-yl)heptanoic acid

There total 7 articles about 7-((2S)-2-{(1E,3S)-3-hydroxy-4-[3-(methoxymethyl)phenyl]but-1-enyl}-5-oxopyrrolidin-1-yl)heptanoic 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: 76.0%

: 1369917-34-9
ethyl 7-[(2S)-2-{(1E,3S)-3-hydroxy-4-[3-(methoxymethyl)phenyl]-1-buten-1-yl}-5-oxo-1-pyrrolidinyl]heptanoate

: 1369916-97-1
7-((2S)-2-{(1E,3S)-3-hydroxy-4-[3-(methoxymethyl)phenyl]but-1-enyl}-5-oxopyrrolidin-1-yl)heptanoic acid

Guidance literature:: With water; sodium hydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; at 20 ℃;
DOI:10.1248/cpb.59.1494

Reference yield:

: 1369917-30-5
ethyl 7-[(2S)-2-{(1E)-4-[3-(methoxymethyl)phenyl]-3-oxo-1-buten-1-yl}-5-oxo-1-pyrrolidinyl]heptanoate

: 1369916-97-1
7-((2S)-2-{(1E,3S)-3-hydroxy-4-[3-(methoxymethyl)phenyl]but-1-enyl}-5-oxopyrrolidin-1-yl)heptanoic acid

Guidance literature:: Multi-step reaction with 2 steps

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

2: water; sodium hydroxide / tetrahydrofuran; 1,2-dimethoxyethane; ethanol / 20 °C

With borane-THF; water; sodium hydroxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; toluene;
DOI:10.1248/cpb.59.1494

Reference yield:

: 29823-18-5
ethyl 7-bromoheptanoate

: 1369916-97-1
7-((2S)-2-{(1E,3S)-3-hydroxy-4-[3-(methoxymethyl)phenyl]but-1-enyl}-5-oxopyrrolidin-1-yl)heptanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 60 °C / Inert atmosphere

1.2: 0 - 80 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

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

4.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere

4.2: 0 °C / Inert atmosphere

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

6.1: water; sodium hydroxide / tetrahydrofuran; 1,2-dimethoxyethane; ethanol / 20 °C

With borane-THF; tetrabutyl ammonium fluoride; 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; ethanol; ethyl acetate; N,N-dimethyl-formamide; toluene; mineral oil; 4.1: Horner-Wadsworth-Emmons olefination / 4.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1248/cpb.59.1494