Acetic Acid → (2R,5S)-2-Methyl-5-(2-oxo-oxazolidin-3-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester, acetate salt

HRID 1475471Notes

Reaction equation

HRID 1475471 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([O:9][C:10]([N:12]1[CH2:17][C@H:16]([CH2:18][N:19]2[CH2:23][CH2:22][O:21][C:20]2=[O:24])[N:15](CC2C=CC=CC=2)[CH2:14][C@H:13]1[CH3:32])=[O:11])([CH3:8])([CH3:7])[CH3:6]>CCO.[Pd]>[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([O:9][C:10]([N:12]1[CH2:17][C@H:16]([CH2:18][N:19]2[CH2:23][CH2:22][O:21][C:20]2=[O:24])[NH:15][CH2:14][C@H:13]1[CH3:32])=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 70980546(2R,5S)-4-Benzyl-2-methyl-5-(2-oxo-oxazolidin-3-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 131732781(2R,5S)-2-Methyl-5-(2-oxo-oxazolidin-3-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester, acetate salt

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Acetic acid (1.5 mL) and Pd/C (400 mg) were added to a solution of (2R,5S)-4-benzyl-2-methyl-5-(2-oxo-oxazolidin-3-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester (450 mg, 1.15 mmol) in EtOH (20 mL) and the resulting mixture was reacted under H2 (1 bar) for 3 h. The catalyst was removed by filtration through a plug of Celite and the solvent was removed in vacuo to give the title compound (530 mg) as a colourless gum. MS: [M+H]+=300.

Workup

  1. customthe resulting mixture was reacted under H2 (1 bar) for 3 h
  2. customThe catalyst was removed by filtration through a plug of Celite
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-32f3241ab7b94ed4b2a8e44184bdab4d
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

Loading…