3-Oxazolidinecarboxylic acid, 4-[(1E)-3-methoxy-3-oxo-1-propenyl]-4-methyl-5-oxo-2-phenyl-, phenylmethyl ester, (2R,4S)-

Base Information

• Chemical Name: 3-Oxazolidinecarboxylic acid, 4-[(1E)-3-methoxy-3-oxo-1-propenyl]-4-methyl-5-oxo-2-phenyl-, phenylmethyl ester, (2R,4S)-
• CAS No.: 537040-12-3
• Molecular Formula: C22H21NO6
• Molecular Weight: 395.412
• Mol file: 537040-12-3.mol

Synonyms:

Chemical Property of 3-Oxazolidinecarboxylic acid, 4-[(1E)-3-methoxy-3-oxo-1-propenyl]-4-methyl-5-oxo-2-phenyl-, phenylmethyl ester, (2R,4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Oxazolidinecarboxylic acid, 4-[(1E)-3-methoxy-3-oxo-1-propenyl]-4-methyl-5-oxo-2-phenyl-, phenylmethyl ester, (2R,4S)-

There total 1 articles about 3-Oxazolidinecarboxylic acid, 4-[(1E)-3-methoxy-3-oxo-1-propenyl]-4-methyl-5-oxo-2-phenyl-, phenylmethyl ester, (2R,4S)- 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: 62.0%

methyl (2E)-3-bromoacrylate (6213-87-2) + (2R,4R)-3-<(Benzyloxy)carbonyl>-4-methyl-2-phenyl-1,3-oxazolidin-5-one (135923-86-3,135923-87-4,143564-89-0) → (2R,4S)-2-phenyl-3-(carbobenzyloxy)-4-methyl-4-[(3-methoxy)carbonyl-(1E)-propenyl]oxazolidin-5-one (537040-12-3)

Guidance literature:

(2R,4R)-3-<(Benzyloxy)carbonyl>-4-methyl-2-phenyl-1,3-oxazolidin-5-one; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 0.75h;

methyl (2E)-3-bromoacrylate; In tetrahydrofuran; at -78 ℃; for 0.75h;

DOI:10.1016/S0957-4166(03)00049-1

Reference yield: 67.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (2R,4S)-2-phenyl-3-(carbobenzyloxy)-4-methyl-4-[(3-methoxy)carbonyl-(1E)-propenyl]oxazolidin-5-one (537040-12-3) → (2R,4S)-4-((R)-2-Methoxycarbonyl-cyclopropyl)-4-methyl-5-oxo-2-phenyl-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:

palladium diacetate; In diethyl ether; at 20 ℃;

DOI:10.1016/S0957-4166(03)00049-1

Reference yield:

(2R,4S)-2-phenyl-3-(carbobenzyloxy)-4-methyl-4-[(3-methoxy)carbonyl-(1E)-propenyl]oxazolidin-5-one (537040-12-3) → (2S,3S,4S)-N-carbobenzyloxy-2-methyl-2-(carboxycyclopropyl)glycine (537040-14-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / Pd(OAc)2 / diethyl ether / 20 °C

2: 100 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 25 °C

With lithium hydroxide; palladium diacetate; In tetrahydrofuran; diethyl ether; water;

DOI:10.1016/S0957-4166(03)00049-1

upstream raw materials:

methyl (2E)-3-bromoacrylate

(2R,4R)-3-<(Benzyloxy)carbonyl>-4-methyl-2-phenyl-1,3-oxazolidin-5-one

Downstream raw materials:

(2S,3S,4S)-2-methyl-2-(carboxycyclopropyl)glycine

(2S,3S,4S)-N-carbobenzyloxy-2-methyl-2-(carboxycyclopropyl)glycine