2-[4-(3-((4S)-2-oxo-4-phenyl)-(1,3-oxazolidin-3-yl))]-(1S,2S)-2-{[(tert-butyl)oxycarbonylmethyl-3-oxo-1-vinylpropyl]phenyl}propane-1,3-dioic acid bis(1,1-dimethylethyl) ester

Base Information

• Chemical Name: 2-[4-(3-((4S)-2-oxo-4-phenyl)-(1,3-oxazolidin-3-yl))]-(1S,2S)-2-{[(tert-butyl)oxycarbonylmethyl-3-oxo-1-vinylpropyl]phenyl}propane-1,3-dioic acid bis(1,1-dimethylethyl) ester
• CAS No.: 641638-40-6
• Molecular Formula: C₃₇H₄₇NO₉
• Molecular Weight: 649.781

Synonyms:2-[4-(3-((4S)-2-oxo-4-phenyl)-(1,3-oxazolidin-3-yl))]-(1S,2S)-2-{[(tert-butyl)oxycarbonylmethyl-3-oxo-1-vinylpropyl]phenyl}propane-1,3-dioic acid bis(1,1-dimethylethyl) ester

Chemical Property of 2-[4-(3-((4S)-2-oxo-4-phenyl)-(1,3-oxazolidin-3-yl))]-(1S,2S)-2-{[(tert-butyl)oxycarbonylmethyl-3-oxo-1-vinylpropyl]phenyl}propane-1,3-dioic acid bis(1,1-dimethylethyl) ester

Chemical Property:

Purity/Quality:

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Technology Process of 2-[4-(3-((4S)-2-oxo-4-phenyl)-(1,3-oxazolidin-3-yl))]-(1S,2S)-2-{[(tert-butyl)oxycarbonylmethyl-3-oxo-1-vinylpropyl]phenyl}propane-1,3-dioic acid bis(1,1-dimethylethyl) ester

There total 5 articles about 2-[4-(3-((4S)-2-oxo-4-phenyl)-(1,3-oxazolidin-3-yl))]-(1S,2S)-2-{[(tert-butyl)oxycarbonylmethyl-3-oxo-1-vinylpropyl]phenyl}propane-1,3-dioic acid bis(1,1-dimethylethyl) ester 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: 53.0%

t-butyl iodoacetate (49827-15-8) + 2-{4-[(1R)-3-((4S)-2-oxo-4-phenyl-(1,3-oxazolidin-3-yl))-3-oxo-1-vinylpropyl]phenyl}propane-1,3-dioic acid bis(1,1-dimethylethyl) ester (641638-39-3) → 2-[4-(3-((4S)-2-oxo-4-phenyl)-(1,3-oxazolidin-3-yl))]-(1S,2S)-2-{[(tert-butyl)oxycarbonylmethyl-3-oxo-1-vinylpropyl]phenyl}propane-1,3-dioic acid bis(1,1-dimethylethyl) ester (641638-40-6)

Guidance literature:

2-{4-[(1R)-3-((4S)-2-oxo-4-phenyl-(1,3-oxazolidin-3-yl))-3-oxo-1-vinylpropyl]phenyl}propane-1,3-dioic acid bis(1,1-dimethylethyl) ester; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

t-butyl iodoacetate; In tetrahydrofuran; at -78 ℃; for 4h;

DOI:10.1021/jm030510e

Reference yield:

t-butyl malonate (541-16-2) → 2-[4-(3-((4S)-2-oxo-4-phenyl)-(1,3-oxazolidin-3-yl))]-(1S,2S)-2-{[(tert-butyl)oxycarbonylmethyl-3-oxo-1-vinylpropyl]phenyl}propane-1,3-dioic acid bis(1,1-dimethylethyl) ester (641638-40-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride; hexamethylphosphoramide / dioxane / 1 h / 20 °C

1.2: 75 percent / CuBr / dioxane / 3 h / Heating

2.1: 87 percent / Et₃N; Pd(OAc)2; (o-tolyl)3P / 16 h / Heating

3.1: PhSCu / diethyl ether; tetrahydrofuran / 0.33 h / -40 °C

3.2: 58 percent / tetrahydrofuran; diethyl ether / 3 h / -40 °C

4.1: N-sodiohexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

4.2: 53 percent / tetrahydrofuran / 4 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; palladium diacetate; sodium hexamethyldisilazane; copper(I) thiophenolate; sodium hydride; triethylamine; tris-(o-tolyl)phosphine; In tetrahydrofuran; 1,4-dioxane; diethyl ether;

DOI:10.1021/jm030510e

Reference yield:

1,4-bromoiodobenzene (589-87-7) → 2-[4-(3-((4S)-2-oxo-4-phenyl)-(1,3-oxazolidin-3-yl))]-(1S,2S)-2-{[(tert-butyl)oxycarbonylmethyl-3-oxo-1-vinylpropyl]phenyl}propane-1,3-dioic acid bis(1,1-dimethylethyl) ester (641638-40-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride; hexamethylphosphoramide / dioxane / 1 h / 20 °C

1.2: 75 percent / CuBr / dioxane / 3 h / Heating

2.1: 87 percent / Et₃N; Pd(OAc)2; (o-tolyl)3P / 16 h / Heating

3.1: PhSCu / diethyl ether; tetrahydrofuran / 0.33 h / -40 °C

3.2: 58 percent / tetrahydrofuran; diethyl ether / 3 h / -40 °C

4.1: N-sodiohexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

4.2: 53 percent / tetrahydrofuran / 4 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; palladium diacetate; sodium hexamethyldisilazane; copper(I) thiophenolate; sodium hydride; triethylamine; tris-(o-tolyl)phosphine; In tetrahydrofuran; 1,4-dioxane; diethyl ether;

DOI:10.1021/jm030510e

upstream raw materials:

t-butyl iodoacetate

2-{4-[(1R)-3-((4S)-2-oxo-4-phenyl-(1,3-oxazolidin-3-yl))-3-oxo-1-vinylpropyl]phenyl}propane-1,3-dioic acid bis(1,1-dimethylethyl) ester

t-butyl malonate

1,4-bromoiodobenzene

Downstream raw materials:

2-{4-[(S)-1-((S)-2-tert-Butoxycarbonyl-1-{1-[(S)-2-carbamoyl-1-((S)-2-naphthalen-1-ylmethyl-pent-4-enylcarbamoyl)-ethylcarbamoyl]-cyclohexylcarbamoyl}-ethyl)-allyl]-phenyl}-malonic acid di-tert-butyl ester

2-(4-((9S,10S,14S,18S)-7,16,19-triaza-9-{[(tert-butyl)oxycarbonyl]methyl}-18-(carbamoylmethyl)-14-(naphthylmethyl)-8,17,20-trioxospiro[5,14]icos-11-en-10-yl)phenyl)propane-1,3-dioic acid bis(1,1-dimethylethyl) ester

(2S,3S)-3-(4-{bis[(tert-butyl)oxycarbonyl]methyl}-phenyl)-2-{[(tert-butyl)oxycarbonyl]methyl}-pent-4-enoic acid

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