Trifluoroacetic acid → N-[(5S)-3-{3-Fluoro-4[4-(2-piperazin-1-yl-acetyl)-piperazin-1-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl]-acetamide

HRID 1163344Notes

Reaction equation

HRID 1163344 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:33][C@H:32]([CH2:34][NH:35][C:36](=[O:38])[CH3:37])[O:31][C:30]4=[O:39])=[CH:25][C:24]=3[F:40])[CH2:19][CH2:18]2)=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[F:40][C:24]1[CH:25]=[C:26]([N:29]2[CH2:33][C@H:32]([CH2:34][NH:35][C:36](=[O:38])[CH3:37])[O:31][C:30]2=[O:39])[CH:27]=[CH:28][C:23]=1[N:20]1[CH2:19][CH2:18][N:17]([C:15](=[O:16])[CH2:14][N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 672739974-[2-(4-{4-[(5S)-5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-piperazin-1-yl)-2-oxo-ethyl]-piperazine-1-carboxylic Acid Tert-Butyl Ester

Product 1

HCID 67274298N-[(5S)-3-{3-Fluoro-4[4-(2-piperazin-1-yl-acetyl)-piperazin-1-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl]-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.490 g of 4-[2-(4-{4-[(5S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-piperazin-1-yl)-2-oxo-ethyl]-piperazine-1-carboxylic acid tert-butyl ester (0.87 mmol) in 2 ml dichloromethane was treated with 2 ml of TFA. The reaction was monitored by TLC. The solvent was evaporated and the residue dissolved in water. The water layer was neutralized with ammonium hydroxide and freeze-dried.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in water
  3. customfreeze-dried

Sources & evidence

ORD record
ord-034600d25b7e438a81d39a0784eaaee7
Source dataset
uspto-grants-2010_10
Patent number
US07820823B2

Reaction notes

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