Trifluoroacetic acid → (3S)-3-(4-Chlorobenzyl)-4-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-4-oxo-butyric acid

HRID 1192346Notes

Reaction equation

HRID 1192346 reaction equation
C([O:5][C:6](=[O:32])[CH2:7][C@H:8]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)[C:9]([N:11]1[C@H:15]([CH3:16])[C@H:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:13][C:12]1=[O:23])=[O:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([CH2:24][C@H:8]([C:9]([N:11]2[C@H:15]([CH3:16])[C@H:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[O:13][C:12]2=[O:23])=[O:10])[CH2:7][C:6]([OH:32])=[O:5])=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67540437(3S)-3-(4-Chlorobenzyl)-4-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-4-oxo-butyric acid tert-butyl ester

Product 1

HCID 67539677(3S)-3-(4-Chlorobenzyl)-4-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-4-oxo-butyric acidYield 101.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3S)-3-(4-Chlorobenzyl)-4-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-4-oxo-butyric acid tert-butyl ester (5.1 g, 11 mmol) in DCM (100 mL) was treated with TFA (50 mL) and stirred at room temperature for 1 hour. The solution was concentrated in vacuo, taken up into toluene and then conc. in vacuo. Placed on high vacuum for 6 hours to give (3S)-3-(4-Chlorobenzyl)-4-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-4-oxo-butyric acid (4.5 g, 100%.) 1H NMR (CDCl3, 400 MHz) δ 7.44-7.37 (3H, m), 7.31-7.21 (6H, m), 5.48 (1H, d, J 6.9 Hz), 4.70-4.63 (1H, m), 4.50-4.42 (1H, m), 3.05 (1H, dd, J 13.3 and 6.2 Hz), 2.89 (1H, dd, J 17.7 and 10.6 Hz), 2.63 (1H, dd, J 13.2 and 9.0 Hz), 2.43 (1H, dd, J 17.6 and 4.4 Hz), 0.86 (3H, d, J 6.6 Hz.)

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. waitPlaced on high vacuum for 6 hours

Sources & evidence

ORD record
ord-15f59b96c56a443dac871f02f0202f01
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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