Methanol → HCID 68090242, compound

HRID 2362377Notes

Reaction equation

HRID 2362377 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:12]([C:13]([OH:15])=[O:14])[O:11][C:10](=[O:16])[NH:9]2)[CH:5]=[CH:6][CH:7]=1.CO.[CH3:19][Si](C=[N+]=[N-])(C)C>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:12]([C:13]([O:15][CH3:19])=[O:14])[O:11][C:10](=[O:16])[NH:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 69081623HCID 69081623, compound

Product 1

HCID 68090242HCID 68090242, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4R,5S)-4-(3-bromophenyl)-2-oxooxazolidine-5-carboxylic acid (20 mg, 0.070 mmol) in tetrahydrofuran (2 mL)/methanol (0.500 mL) was added trimethylsilyldiazomethane (0.063 mL, 0.126 mmol) dropwise at 0° C. After 3 h, the reaction was allowed to warm to ambient temperature and stirred for an additional 15 h, at which time it was concentrated in vacuo to provide (4R,5S)-methyl 4-(3-bromophenyl)-2-oxooxazolidine-5-carboxylate (18.2 mg, 0.058 mmol, 82% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 3.78 (s, 3H) 4.98 (d, J=4.88 Hz, 1H) 5.01-5.04 (m, 1H) 7.37-7.45 (m, 2H) 7.56 (s, 1H) 7.57-7.61 (m, 1H) 8.60 (s, 1H). Mass spec.: 301.77 (MH)+.

Workup

  1. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-e57b3471c91944e8a497b0bfbc9ff375
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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