(S)-4-Benzyl-2-oxazolidinone → (4S)-4-benzyl-3-(5,5,5-trifluoropentanoyl)-1,3-oxazolidin-2-one

HRID 68350

Reaction equation

HRID 68350 reaction equation
[F:1][C:2]([F:10])([F:9])[CH2:3][CH2:4][CH2:5][C:6]([OH:8])=O.[CH2:11]([C@H:18]1[CH2:22][O:21][C:20](=[O:23])[NH:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([C@H:18]1[CH2:22][O:21][C:20](=[O:23])[N:19]1[C:6](=[O:8])[CH2:5][CH2:4][CH2:3][C:2]([F:1])([F:10])[F:9])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 27824465,5,5-trifluoropentanoic Acid

Product 1

HCID 68314831(4S)-4-benzyl-3-(5,5,5-trifluoropentanoyl)-1,3-oxazolidin-2-one

Procedure

Preparation 1N was prepared from 5,5,5-trifluoropentanoic acid (3.35 g, 21.46 mmol) and (4S)-4-benzyl-1,3-oxazolidin-2-one (3.80 g, 21.46 mmol) by the general methods shown for Preparation 1B. Preparation 1N (5.67 g, 84%) was obtained as a colorless viscous oil: 1H NMR (400 MHz, CDCl3) δ ppm 7.32-7.39 (2H, m), 7.30 (1H, d, J=7.05 Hz), 7.18-7.25 (2H, m), 4.64-4.74 (1H, m), 4.17-4.27 (2H, m), 3.31 (1H, dd, J=13.35, 3.27 Hz), 3.00-3.11 (2H, m), 2.79 (1H, dd, J=13.35, 9.57 Hz), 2.16-2.28 (2H, m), 1.93-2.04 (2H, m).

Workup

  1. customPreparation 1N
  2. customPreparation 1N (5.67 g, 84%)
  3. customwas obtained as a colorless viscous oil

Sources & evidence

ORD record
ord-ff3671e002d644b896c69a79e2748a9d
Source dataset
uspto-grants-2014_09
Patent number
US08822454B2

Linked notes

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