(R)-4-((S)-1-fluoroethyl)-3-(4-methoxybenzyl)oxazolidin-2-one → (R)-4-((S)-1-Fluoroethyl)oxazolidin-2-one

HRID 57507Notes

Reaction equation

HRID 57507 reaction equation
[F:1][C@H:2]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1CC1C=CC(OC)=CC=1)[CH3:3]>C(O)(C(F)(F)F)=O>[F:1][C@H:2]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[NH:5]1)[CH3:3]

Participants

3

Reactant 1

HCID 90423361(R)-4-((S)-1-fluoroethyl)-3-(4-methoxybenzyl)oxazolidin-2-one

Product 1

HCID 90422887(R)-4-((S)-1-Fluoroethyl)oxazolidin-2-oneYield 87.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (R)-4-((S)-1-fluoroethyl)-3-(4-methoxybenzyl)oxazolidin-2-one (1.98 g 7.8 mmol) in 40 mL TFA was heated at 65° C. for 16 h. The reaction mixture was concentrated to remove TFA. Flash column chromatography (EtOAc/CH2Cl2, 0 to 100%) gave 0.91 g (R)-4-((S)-1-fluoroethyl)-oxazolidin-2-one as a pale brown solid. TLC (1:2 heptane:EtOAc) Rf=0.25. 1H NMR (400 MHz, CDCl3) δ 5.60 (br s, 1H), 4.72-4.54 (m, 1H), 4.51 (td, J=8.9, 0.9 Hz, 1H), 4.32 (dd, J=9.2, 4.8 Hz, 1H), 4.02-3.88 (m, 1H), 1.38 (dd, J=24.0, 6.3 Hz, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove TFA

Sources & evidence

ORD record
ord-a68cf88ff56d486888961dac6dc4077a
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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