Acetic Acid → HCID 131719942, compound

HRID 977222Notes

Reaction equation

HRID 977222 reaction equation
[ClH:1].Cl.[NH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH:14]([C:16]([N:18]3[CH2:23][CH2:22][N:21]([CH2:24][C:25]([O:27]CC4C=CC=CC=4)=[O:26])[CH2:20][CH2:19]3)=[O:17])[O:13][C:12]2=[O:35])=[CH:7][CH:6]=1.O.C(O)(=O)C>CO.[Pd].C>[ClH:1].[ClH:1].[NH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH:14]([C:16]([N:18]3[CH2:19][CH2:20][N:21]([CH2:24][C:25]([OH:27])=[O:26])[CH2:22][CH2:23]3)=[O:17])[O:13][C:12]2=[O:35])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 131719941HCID 131719941, compound

Product 1

HCID 131719942HCID 131719942, compound

Reagents, catalysts & solvents 2

HCID 14818447PalladiumcarbonCatalystHCID 887MethanolSolvent

Procedure

0.6 g of benzyl 2-{1-[3-(4-aminomethylphenyl)-2-oxo-5-oxazolidinylcarbonyl]-4-piperazinyl}acetate, dihydrochloride, is hydrogenated over Pd/charcoal, in a mixture of 30 ml of methanol, 5 ml of water and 5 ml of glacial acetic acid. The reaction mixture is filtered and the filtrate is concentrated in vacuo. Trituration of the crude product with ethyl acetate gives 2-{1-[3-(4-aminomethylphenyl)-2-oxo-5-oxazolidinylcarbonyl]-4-piperazinyl}acetic acid, dihydrochloride, m.p. 91° (decomposition).

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-f59cd6a78abf4da99415f625138088d4
Source dataset
uspto-grants-1997_03
Patent number
US05614535

Reaction notes

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