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

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Chemical Name:4-(2-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)benzoic acid
CAS No.:494223-72-2
Molecular Formula:C₂₄H₂₇NO₄
Molecular Weight:393.483
Hs Code.:

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

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

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

There total 9 articles about 4-(2-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)benzoic 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:

: 1365177-62-3
ethyl 4-(2-{(2R)-2-[(1E,3S)-3-(tert-butyldimethylsilyloxy)-4-(3-methylphenyl)-1-buten-1-yl]-5-oxo-1-pyrrolidinyl}ethyl)benzoate

: 494223-72-2
4-(2-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)benzoic acid

Guidance literature:: ethyl 4-(2-{(2R)-2-[(1E,3S)-3-(tert-butyldimethylsilyloxy)-4-(3-methylphenyl)-1-buten-1-yl]-5-oxo-1-pyrrolidinyl}ethyl)benzoate; With sodium hydroxide; In methanol; 1,2-dimethoxyethane; water; for 2h;

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

Reference yield:

: 494224-49-6
(R)-ethyl 4-(tert-butoxycarbonylamino)-5-oxopentanoate

: 494223-72-2
4-(2-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)benzoic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

1.2: 2 h / 20 °C

2.1: 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

3.1: hydrogenchloride / 1,4-dioxane; ethanol / 8 h / 20 °C / Inert atmosphere

4.1: tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

4.2: 16 h / 0 - 20 °C

5.1: 1H-imidazole / N,N-dimethyl-formamide / 6 h / 50 °C / Inert atmosphere

6.1: 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate / dimethyl sulfoxide / 8 h / 80 °C / Inert atmosphere

7.1: sodium hydroxide / methanol; 1,2-dimethoxyethane; water / 2 h

With 1H-imidazole; hydrogenchloride; 1,1'-bis-(diphenylphosphino)ferrocene; borane-THF; palladium diacetate; sodium hydride; sodium hydroxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; ethanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; mineral oil; 1.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.bmc.2012.02.018

Reference yield:

: 597577-78-1
(4R)-4-t-butoxycarbonylamino-5-hydroxypentanoic acid ethyl ester

: 494223-72-2
4-(2-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)benzoic acid

Guidance literature:: Multi-step reaction with 8 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.67 h / -70 - -40 °C

1.2: 0.5 h / -40 - -5 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

2.2: 2 h / 20 °C

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: hydrogenchloride / 1,4-dioxane; ethanol / 8 h / 20 °C / Inert atmosphere

5.1: tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

5.2: 16 h / 0 - 20 °C

6.1: 1H-imidazole / N,N-dimethyl-formamide / 6 h / 50 °C / Inert atmosphere

7.1: 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate / dimethyl sulfoxide / 8 h / 80 °C / Inert atmosphere

8.1: sodium hydroxide / methanol; 1,2-dimethoxyethane; water / 2 h

With 1H-imidazole; hydrogenchloride; 1,1'-bis-(diphenylphosphino)ferrocene; borane-THF; oxalyl dichloride; palladium diacetate; sodium hydride; dimethyl sulfoxide; sodium hydroxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; mineral oil; 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.bmc.2012.02.018