Trifluoroacetic acid → (S)-N-[[3-[3,5-difluoro-4-[4-[2-(1-piperidinyl)ethyl]-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 1078526Notes

Reaction equation

HRID 1078526 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:22]2[CH2:26][CH:25]([CH2:27][NH:28][C:29](=[O:31])[CH3:30])[O:24][C:23]2=[O:32])[CH:5]=[C:6]([F:21])[C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14](OC(C)(C)C)=O)[CH2:10][CH2:9]1.F[C:34](F)(F)[C:35](O)=O>C(Cl)Cl>[F:21][C:6]1[CH:5]=[C:4]([N:22]2[CH2:26][C@H:25]([CH2:27][NH:28][C:29](=[O:31])[CH3:30])[O:24][C:23]2=[O:32])[CH:3]=[C:2]([F:1])[C:7]=1[N:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:9][N:8]2[CH2:35][CH2:34][CH2:3][CH2:2][CH2:7]2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21462594N-[[3-[3,5-difluoro-4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Product 1

HCID 54560046(S)-N-[[3-[3,5-difluoro-4-[4-[2-(1-piperidinyl)ethyl]-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamideYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The N-[[3-[3,5-difluoro-4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (1.00 g, 2.20 mmol) was dissolved in CH2Cl2 (6 mL) and cooled to 0° C. with an ice bath. Trifluoroacetic acid (20 mL) was added, the cooling bath removed, and the reaction mixture allowed to warm to ambient temperature over 1 h. The reaction mixture was then concentrated in vacuo and the residue dissolved in H2O (15 mL). The resultant solution was added to Bio Rad AG-1-X8 ion exchange resin (12 mL; OH- form, washed with H2O until neutral), additional H2O (5 mL) was added, and the mixture stirred for 10 min. The mixture was then filtered and the resin washed with additional H2O (3×5 mL). The aqueous filtrate was lyophilized to give 0.559 g (72%) of the title compound as a white solid with mp 108°-112° C. (dec).

Workup

  1. customthe cooling bath removed
  2. temperatureto warm to ambient temperature over 1 h
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. dissolutionthe residue dissolved in H2O (15 mL)
  5. additionThe resultant solution was added to Bio Rad AG-1-X8 ion exchange resin (12 mL; OH- form, washed with H2O until neutral), additional H2O (5 mL)
  6. additionwas added
  7. filtrationThe mixture was then filtered
  8. washthe resin washed with additional H2O (3×5 mL)

Sources & evidence

ORD record
ord-922441124d684df8ad71a9a84055357f
Source dataset
uspto-grants-1996_08
Patent number
US05547950

Reaction notes

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