Diethyl Ether → N-[[(5S)-3-[3-fluoro-4-(hydroxycarbamoyl)phenyl]-2-oxo-oxazolidin-5-yl]methyl]acetamide

HRID 1979281Notes

Reaction equation

HRID 1979281 reaction equation
[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18](OC3C(F)=C(F)C(F)=C(F)C=3F)=[O:19])=[C:14]([F:32])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2].C[Si](C)(C)[O:35][NH2:36].C(OCC)C>O1CCCC1>[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([NH:36][OH:35])=[O:19])=[C:14]([F:32])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2734666O-(Trimethylsilyl)hydroxylamineHCID 229661965-(S)-acetamidomethyl-3-[4'-(pentafluorophenoxy)carbonyl-3'-fluorophenyl]oxazolidine-2-one

Product 1

HCID 485749N-[[(5S)-3-[3-fluoro-4-(hydroxycarbamoyl)phenyl]-2-oxo-oxazolidin-5-yl]methyl]acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared according to Method D of the General Procedures for Preparation of 5-(S)-(N-Acylaminomethyl)-3-[4′-(4″-(un)substituted amino)carbonyl-3′-fluorophenyl]oxazolidine-2-ones from 5-(S)-acetamidomethyl-3-[4′-(pentafluorophenyl)oxycarbonyl-3′-fluorophenyl]-oxazolidine-2-one (0.046 g, 0.1 mmol) and O-trimethylsilylhydroxylamine (0.052 mL, ca. 0.5 mmol) in tetrahydrofuran (1 mL). The synthesis was performed for 2 h at r.t. Diethyl ether (4 mL) was added, the precipitated product washed with diethyl ether, tetrahydrofuran (2×0.5 mL), excess ether, and dried in vacuo. MS: 312 [M+H]+. Rt 2.8 min. 1H NMR.

Workup

  1. customPrepared
  2. washthe precipitated product washed with diethyl ether, tetrahydrofuran (2×0.5 mL), excess ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-4aaeb903c57949bdb4de1d637c007882
Source dataset
uspto-grants-2001_05
Patent number
US06239152B1

Reaction notes

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