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

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Chemical Name:2-(3-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}propyl)-1,3-oxazole-4-carboxylic acid
CAS No.:494223-75-5
Molecular Formula:C₂₂H₂₆N₂O₅
Molecular Weight:398.459
Hs Code.:

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

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

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

There total 10 articles about 2-(3-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}propyl)-1,3-oxazole-4-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: 70.0%

: 1355026-82-2
methyl 2-(3-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)-1-buten-1-yl]-5-oxo-1-pyrrolidinyl}propyl)-1,3-oxazole-4-carboxylate

: 494223-75-5
2-(3-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}propyl)-1,3-oxazole-4-carboxylic acid

Guidance literature:: methyl 2-(3-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)-1-buten-1-yl]-5-oxo-1-pyrrolidinyl}propyl)-1,3-oxazole-4-carboxylate; 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

: 494223-75-5
2-(3-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}propyl)-1,3-oxazole-4-carboxylic acid

Guidance literature:: Multi-step reaction with 5 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: 1 h / 50 °C / Inert atmosphere

4.2: 15 h / 0 - 20 °C / Inert atmosphere

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

With hydrogenchloride; borane-THF; 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; 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

: 494223-75-5
2-(3-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl}propyl)-1,3-oxazole-4-carboxylic acid

Guidance literature:: Multi-step reaction with 6 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: 1 h / 50 °C / Inert atmosphere

5.2: 15 h / 0 - 20 °C / Inert atmosphere

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

With hydrogenchloride; borane-THF; oxalyl dichloride; 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; toluene; mineral oil; 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.bmc.2012.02.018