tert-butyl (4R,5S)-4-(4-methoxyphenyl)-2-oxo-1,3-oxazolidine-5-carboxylate

Base Information

• Chemical Name: tert-butyl (4R,5S)-4-(4-methoxyphenyl)-2-oxo-1,3-oxazolidine-5-carboxylate
• CAS No.: 714951-44-7
• Molecular Formula: C₁₅H₁₉NO₅
• Molecular Weight: 293.32
• Mol file: 714951-44-7.mol

Synonyms:tert-butyl (4R,5S)-4-(4-methoxyphenyl)-2-oxo-1,3-oxazolidine-5-carboxylate

Chemical Property of tert-butyl (4R,5S)-4-(4-methoxyphenyl)-2-oxo-1,3-oxazolidine-5-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (4R,5S)-4-(4-methoxyphenyl)-2-oxo-1,3-oxazolidine-5-carboxylate

There total 6 articles about tert-butyl (4R,5S)-4-(4-methoxyphenyl)-2-oxo-1,3-oxazolidine-5-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: 77.0%

tert-butyl (2R,3R)-3-[(tert-butoxycarbonyl)amino]-2-(mesyloxy)-3-(4-methoxyphenyl)propanoate (714951-43-6) → tert-butyl (4R,5S)-4-(4-methoxyphenyl)-2-oxo-1,3-oxazolidine-5-carboxylate (714951-44-7)

Guidance literature:

In N,N-dimethyl-formamide; for 42h;

DOI:10.1039/b402437k

Reference yield: 62.0%

(4R,5S)-tert-butyl 3,4-bis(4-methoxyphenyl)-2-oxooxazolidine-5-carboxylate (1254709-10-8) → tert-butyl (4R,5S)-4-(4-methoxyphenyl)-2-oxo-1,3-oxazolidine-5-carboxylate (714951-44-7)

Guidance literature:

With ammonium cerium (IV) nitrate; In water; acetonitrile; at 0 ℃; Inert atmosphere;

DOI:10.1021/jo101559p

Reference yield:

tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(4'-methoxyphenyl)propanoate (714951-38-9) → tert-butyl (4R,5S)-4-(4-methoxyphenyl)-2-oxo-1,3-oxazolidine-5-carboxylate (714951-44-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / H₂ / Pearlman's catalyst / methanol / 24 h / 3800 Torr

2: 90 percent / NaHCO₃ / methanol / 12 h / 20 °C / sonication

3: 90 percent / Et₃N / CH₂Cl₂ / 24 h / 20 °C

4: 77 percent / dimethylformamide / 42 h

With hydrogen; sodium hydrogencarbonate; triethylamine; palladium dihydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b402437k

upstream raw materials:

tert-butyl (2R,3R)-3-[(tert-butoxycarbonyl)amino]-2-(mesyloxy)-3-(4-methoxyphenyl)propanoate

tert-butyl (E)-3-(4-methoxyphenyl)prop-2-enoate

tert-butyl (2R,3R)-3-amino-2-hydroxy-3-(4-methoxyphenyl)propanoate

tert-butyl (2R,3R)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-(4-methoxyphenyl)propanoate

Downstream raw materials:

(4R,5S)-5-(hydroxymethyl)-4-(4-methoxyphenyl)-1,3-oxazolidin-2-one