methyl 2-acetylamino-3-[3-pivaloyloxy-5-(4-methoxyphenyl)-4-isoxazolyl]-2-(methoxycarbonyl)propionate

Base Information

• Chemical Name: methyl 2-acetylamino-3-[3-pivaloyloxy-5-(4-methoxyphenyl)-4-isoxazolyl]-2-(methoxycarbonyl)propionate
• CAS No.: 343305-24-8
• Molecular Formula: C₂₃H₂₈N₂O₉
• Molecular Weight: 476.483
• Mol file: 343305-24-8.mol

Synonyms:methyl 2-acetylamino-3-[3-pivaloyloxy-5-(4-methoxyphenyl)-4-isoxazolyl]-2-(methoxycarbonyl)propionate

Chemical Property of methyl 2-acetylamino-3-[3-pivaloyloxy-5-(4-methoxyphenyl)-4-isoxazolyl]-2-(methoxycarbonyl)propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-acetylamino-3-[3-pivaloyloxy-5-(4-methoxyphenyl)-4-isoxazolyl]-2-(methoxycarbonyl)propionate

There total 6 articles about methyl 2-acetylamino-3-[3-pivaloyloxy-5-(4-methoxyphenyl)-4-isoxazolyl]-2-(methoxycarbonyl)propionate 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: 50.0%

dimethyl acetamidomalonate (60187-67-9) + 4-bromomethyl-3-pivaloyloxy-5-(4-methoxyphenyl)isoxazole (343305-21-5) → methyl 2-acetylamino-3-[3-pivaloyloxy-5-(4-methoxyphenyl)-4-isoxazolyl]-2-(methoxycarbonyl)propionate (343305-24-8)

Guidance literature:

dimethyl acetamidomalonate; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.333333h;

4-bromomethyl-3-pivaloyloxy-5-(4-methoxyphenyl)isoxazole; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1002/1521-4184(200102)334:2<62::AID-ARDP62>3.0.CO;2-G

Reference yield:

methyl 4-methoxybenzoate (121-98-2) → methyl 2-acetylamino-3-[3-pivaloyloxy-5-(4-methoxyphenyl)-4-isoxazolyl]-2-(methoxycarbonyl)propionate (343305-24-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 49 percent / NaH / dimethylformamide / 16 h / 20 °C

2.1: HONH₂*HCl; aq. NaOH / methanol / 3 h / -30 °C

2.2: 41 percent / conc. HCl / methanol / 1.5 h / 80 °C

3.1: 95 percent / NEt₃ / CH₂Cl₂ / 20 °C

4.1: 96 percent / NBS / CCl₄ / 72 h / Heating

5.1: NaH / dimethylformamide / 0.33 h / 0 °C

5.2: 50 percent / dimethylformamide / 16 h / 20 °C

With sodium hydroxide; N-Bromosuccinimide; hydroxylamine hydrochloride; sodium hydride; triethylamine; In methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; 1.1: Claisen condensation;

DOI:10.1002/1521-4184(200102)334:2<62::AID-ARDP62>3.0.CO;2-G

Reference yield:

methyl 4-hydroxylbenzoate (99-76-3,156291-94-0) → methyl 2-acetylamino-3-[3-pivaloyloxy-5-(4-methoxyphenyl)-4-isoxazolyl]-2-(methoxycarbonyl)propionate (343305-24-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 0.33 h / 0 °C

1.2: 86 percent / dimethylformamide / 15 h / 20 °C

2.1: 49 percent / NaH / dimethylformamide / 16 h / 20 °C

3.1: HONH₂*HCl; aq. NaOH / methanol / 3 h / -30 °C

3.2: 41 percent / conc. HCl / methanol / 1.5 h / 80 °C

4.1: 95 percent / NEt₃ / CH₂Cl₂ / 20 °C

5.1: 96 percent / NBS / CCl₄ / 72 h / Heating

6.1: NaH / dimethylformamide / 0.33 h / 0 °C

6.2: 50 percent / dimethylformamide / 16 h / 20 °C

With sodium hydroxide; N-Bromosuccinimide; hydroxylamine hydrochloride; sodium hydride; triethylamine; In methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; 2.1: Claisen condensation;

DOI:10.1002/1521-4184(200102)334:2<62::AID-ARDP62>3.0.CO;2-G

upstream raw materials:

dimethyl acetamidomalonate

4-bromomethyl-3-pivaloyloxy-5-(4-methoxyphenyl)isoxazole

methyl 4-methoxybenzoate

methyl 4-hydroxylbenzoate