(1'S,2Z)-pentafluorophenyl 3-[5-(tert-butyl)oxycarbonyl-4,4-dimethyl-3,5-oxazolidinyl]prop-2-enoate

Base Information

• Chemical Name: (1'S,2Z)-pentafluorophenyl 3-[5-(tert-butyl)oxycarbonyl-4,4-dimethyl-3,5-oxazolidinyl]prop-2-enoate
• CAS No.: 173027-95-7
• Molecular Formula: C₁₉H₂₀F₅NO₅
• Molecular Weight: 437.364

Synonyms:(1'S,2Z)-pentafluorophenyl 3-[5-(tert-butyl)oxycarbonyl-4,4-dimethyl-3,5-oxazolidinyl]prop-2-enoate

Chemical Property of (1'S,2Z)-pentafluorophenyl 3-[5-(tert-butyl)oxycarbonyl-4,4-dimethyl-3,5-oxazolidinyl]prop-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (1'S,2Z)-pentafluorophenyl 3-[5-(tert-butyl)oxycarbonyl-4,4-dimethyl-3,5-oxazolidinyl]prop-2-enoate

There total 1 articles about (1'S,2Z)-pentafluorophenyl 3-[5-(tert-butyl)oxycarbonyl-4,4-dimethyl-3,5-oxazolidinyl]prop-2-enoate 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:

(4S)-1,1-dimethylethyl 4-<(Z)-3'-methoxy-3'-oxo-1'-propenyl>-2,2-dimethyl-3-oxazolidinecarboxylate (126587-36-8) → (1'S,2Z)-pentafluorophenyl 3-[5-(tert-butyl)oxycarbonyl-4,4-dimethyl-3,5-oxazolidinyl]prop-2-enoate (173027-95-7)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / tetrahydrofuran / 0 - 20 °C

2: 10.3 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 4-dimethylaminopyridine / CH₂Cl₂ / 20 °C

With dmap; sodium hydroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; 1: Hydrolysis / 2: Esterification;

DOI:10.1016/S0040-4020(98)00219-1

Reference yield: 71.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + (1'S,2Z)-pentafluorophenyl 3-[5-(tert-butyl)oxycarbonyl-4,4-dimethyl-3,5-oxazolidinyl]prop-2-enoate (173027-95-7) → (S)-2,2-Dimethyl-4-((S)-3-pentafluorophenyloxycarbonyl-bicyclo[2.2.1]hept-5-en-2-yl)-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:

In toluene; at 50 ℃; for 72h; sealed tube;

DOI:10.1016/0040-4039(94)02379-P

Reference yield: 67.0%

1-methoxy-3-<(trimethylsilyl)oxy>01,3-butadiene (59414-23-2) + (1'S,2Z)-pentafluorophenyl 3-[5-(tert-butyl)oxycarbonyl-4,4-dimethyl-3,5-oxazolidinyl]prop-2-enoate (173027-95-7) → (S)-4-((1R,2R)-3-Methoxy-5-oxo-2-pentafluorophenyloxycarbonyl-cyclohexyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:

In toluene; at 80 ℃; for 120h; sealed tube;

DOI:10.1016/0040-4039(94)02379-P

upstream raw materials:

(4S)-1,1-dimethylethyl 4-<(Z)-3'-methoxy-3'-oxo-1'-propenyl>-2,2-dimethyl-3-oxazolidinecarboxylate

Downstream raw materials:

(S)-2,2-Dimethyl-4-((1S,2R,3S,4R)-3-pentafluorophenyloxycarbonyl-bicyclo[2.2.1]hept-5-en-2-yl)-oxazolidine-3-carboxylic acid tert-butyl ester

(5S,1'R,6'S)-tert-butyl 5-[6-(methoxycarbonyl)-3-oxocyclohexyl]-2,2-dimethyl-3,1-oxazolidinecarboxylate

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