Phenylmethyl (4R)-4-methyl-2,5-dioxo-3-oxazolidinecarboxylate

Base Information

• Chemical Name: Phenylmethyl (4R)-4-methyl-2,5-dioxo-3-oxazolidinecarboxylate
• CAS No.: 129288-48-8
• Molecular Formula: C₁₂H₁₁NO₅
• Molecular Weight: 249.223
• DSSTox Substance ID: DTXSID601183118
• Mol file: 129288-48-8.mol

Synonyms:129288-48-8;DTXSID601183118;Phenylmethyl (4R)-4-methyl-2,5-dioxo-3-oxazolidinecarboxylate

Chemical Property of Phenylmethyl (4R)-4-methyl-2,5-dioxo-3-oxazolidinecarboxylate

Chemical Property:

• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 249.06372245
• Heavy Atom Count: 18
• Complexity: 362

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(=O)OC(=O)N1C(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C[C@@H]1C(=O)OC(=O)N1C(=O)OCC2=CC=CC=C2

Technology Process of Phenylmethyl (4R)-4-methyl-2,5-dioxo-3-oxazolidinecarboxylate

There total 1 articles about Phenylmethyl (4R)-4-methyl-2,5-dioxo-3-oxazolidinecarboxylate 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:

benzyl chloroformate (501-53-1,94274-21-2) + (4R)-4-methyl-1,3-oxazolidine-2,5-dione (1192-73-0,2224-52-4,4829-14-5,30291-41-9,45530-11-8,45530-21-0) → (R)-benzyl 4-methyl-2,5-dioxooxazolidine-3-carboxylate (129288-48-8,125814-23-5)

Guidance literature:

With 4-methyl-morpholine; In tetrahydrofuran; at 2 - 5 ℃; for 2h; Yield given;

DOI:10.1021/ja00176a063

Reference yield:

methyl (R)-2-amino-5-[(tert-butoxycarbonyl)amino]pentanoate (51186-41-5) + (R)-benzyl 4-methyl-2,5-dioxooxazolidine-3-carboxylate (129288-48-8,125814-23-5) → (5R,8R)-methyl 5,15,15-trimethyl-3,6,13-trioxo-1-phenyl-2,14-dioxa-4,7,12-triazahexadecane-8-carboxylate

Guidance literature:

methyl (R)-2-amino-5-[(tert-butoxycarbonyl)amino]pentanoate; (R)-benzyl 4-methyl-2,5-dioxooxazolidine-3-carboxylate; In tetrahydrofuran; at 0 - 26 ℃; for 2h; Inert atmosphere;

With silicycle amine; In tetrahydrofuran; at 16 - 26 ℃; for 16h;

Reference yield:

(R)-benzyl 4-methyl-2,5-dioxooxazolidine-3-carboxylate (129288-48-8,125814-23-5) → Z-Trp-D-Ala-Ser(OtBu)-OMe

Guidance literature:

Multi-step reaction with 2 steps

1: NMM / tetrahydrofuran

2: 85 percent / H₂ / 10percent Pd-C / tetrahydrofuran / 2.5 h

With 4-methyl-morpholine; hydrogen; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1016/0040-4039(94)02391-N

upstream raw materials:

benzyl chloroformate

(4R)-4-methyl-1,3-oxazolidine-2,5-dione