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

Base Information

Chemical Name: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
CAS No.:1355026-82-2
Molecular Formula:C₂₃H₂₈N₂O₅
Molecular Weight:412.486
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 8 articles about 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 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: 74.0%

: 1365178-59-1
methyl 2-(3-oxopropyl)oxazole-4-carboxylate

: 1355026-77-5
ethyl (4R,5E,7S)-4-amino-7-hydroxy-8-(3-methylphenyl)-5-octenoate hydrochloride

: 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

Guidance literature:: methyl 2-(3-oxopropyl)oxazole-4-carboxylate; ethyl (4R,5E,7S)-4-amino-7-hydroxy-8-(3-methylphenyl)-5-octenoate hydrochloride; at 50 ℃; for 1h; Inert atmosphere;

With sodium tris(acetoxy)borohydride; In tetrahydrofuran; at 0 - 20 ℃; for 15h; Inert atmosphere;
DOI:10.1016/j.bmc.2012.02.018

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 4 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

With hydrogenchloride; borane-THF; sodium hydride; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; 1,4-dioxane; ethanol; 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

: 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

Guidance literature:: Multi-step reaction with 5 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

With hydrogenchloride; borane-THF; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; toluene; mineral oil; 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.bmc.2012.02.018