methyl 2-acetamido-3-[2-(acetoxymethyl)-5-(3-fluorophenyl)-3-oxoisoxazolin-4-yl]-2-(methoxycarbonyl)propanoate

Base Information

Chemical Name:methyl 2-acetamido-3-[2-(acetoxymethyl)-5-(3-fluorophenyl)-3-oxoisoxazolin-4-yl]-2-(methoxycarbonyl)propanoate
CAS No.:203718-28-9
Molecular Formula:C₂₀H₂₁FN₂O₉
Molecular Weight:452.393
Hs Code.:

Synonyms:methyl 2-acetamido-3-[2-(acetoxymethyl)-5-(3-fluorophenyl)-3-oxoisoxazolin-4-yl]-2-(methoxycarbonyl)propanoate

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Chemical Property of methyl 2-acetamido-3-[2-(acetoxymethyl)-5-(3-fluorophenyl)-3-oxoisoxazolin-4-yl]-2-(methoxycarbonyl)propanoate

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Technology Process of methyl 2-acetamido-3-[2-(acetoxymethyl)-5-(3-fluorophenyl)-3-oxoisoxazolin-4-yl]-2-(methoxycarbonyl)propanoate

There total 7 articles about methyl 2-acetamido-3-[2-(acetoxymethyl)-5-(3-fluorophenyl)-3-oxoisoxazolin-4-yl]-2-(methoxycarbonyl)propanoate 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: 72.0%

: 108-24-7
acetic anhydride

: 203718-23-4
methyl 2-acetamido-3-[5-(3-fluorophenyl)-2-(methoxymethyl)-3-oxoisoxazolin-4-yl]-2-(methoxycarbonyl)propanoate

: 203718-28-9
methyl 2-acetamido-3-[2-(acetoxymethyl)-5-(3-fluorophenyl)-3-oxoisoxazolin-4-yl]-2-(methoxycarbonyl)propanoate

Guidance literature:: With boron trifluoride diethyl etherate; In chloroform; at 20 ℃;
DOI:10.1016/S0968-0896(97)10017-7

Reference yield:

: 20595-30-6
3-Fluorocinnamic acid

: 203718-28-9
methyl 2-acetamido-3-[2-(acetoxymethyl)-5-(3-fluorophenyl)-3-oxoisoxazolin-4-yl]-2-(methoxycarbonyl)propanoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 95 percent / conc. H₂SO₄ / 2 h / Heating

2.1: 68 percent / Br₂ / CCl₄ / ice cooling -> room temp.

3.1: 49 percent / NaOH; NH₂OH*HCl / methanol / 8 h / 0 °C / Heating

4.1: aq. HBr / 20 h / 60 °C

5.1: 845 mg / CH₂Cl₂ / 2 h / 20 °C

6.1: NaH / dimethylformamide / 1 h / 0 °C

6.2: 47.5 percent / dimethylformamide / 20 h / 20 °C

7.1: 72 percent / BF₃*Et₂O / CHCl₃ / 20 °C

With sodium hydroxide; sulfuric acid; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; hydrogen bromide; bromine; sodium hydride; In methanol; tetrachloromethane; dichloromethane; chloroform; N,N-dimethyl-formamide; 1.1: Esterification / 2.1: Bromination / 3.1: Cyclization / 4.1: Alkylation / 5.1: Etherification / 6.1: Metallation / 6.2: Sorensen reaction / 7.1: Acetylation;
DOI:10.1016/S0968-0896(97)10017-7

Reference yield:

: 74325-03-4
methyl (E)-m-fluorocinnamate

: 203718-28-9
methyl 2-acetamido-3-[2-(acetoxymethyl)-5-(3-fluorophenyl)-3-oxoisoxazolin-4-yl]-2-(methoxycarbonyl)propanoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 68 percent / Br₂ / CCl₄ / ice cooling -> room temp.

2.1: 49 percent / NaOH; NH₂OH*HCl / methanol / 8 h / 0 °C / Heating

3.1: aq. HBr / 20 h / 60 °C

4.1: 845 mg / CH₂Cl₂ / 2 h / 20 °C

5.1: NaH / dimethylformamide / 1 h / 0 °C

5.2: 47.5 percent / dimethylformamide / 20 h / 20 °C

6.1: 72 percent / BF₃*Et₂O / CHCl₃ / 20 °C

With sodium hydroxide; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; hydrogen bromide; bromine; sodium hydride; In methanol; tetrachloromethane; dichloromethane; chloroform; N,N-dimethyl-formamide; 1.1: Bromination / 2.1: Cyclization / 3.1: Alkylation / 4.1: Etherification / 5.1: Metallation / 5.2: Sorensen reaction / 6.1: Acetylation;
DOI:10.1016/S0968-0896(97)10017-7