Hydrochloric Acid → (S)-4-(4-Aminobenzyl)-1,3-oxazolidin-2-one hydrochloride

HRID 128962Notes

Reaction equation

HRID 128962 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][C@H:9]2[CH2:13][O:12][C:11](=[O:14])[NH:10]2)=[CH:6][CH:5]=1)([O-])=O.O.[ClH:18].[H][H]>[Pd].C(O)C.C(OCC)(=O)C>[ClH:18].[NH2:1][C:4]1[CH:16]=[CH:15][C:7]([CH2:8][C@H:9]2[CH2:13][O:12][C:11](=[O:14])[NH:10]2)=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10353477(S)-4-(4-Nitrobenzyl)oxazolidin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 11543152(S)-4-(4-Aminobenzyl)-1,3-oxazolidin-2-one hydrochloride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of the product from step (c) (0.79 g) and 10% palladium on carbon (0.26 g) in a mixture of ethanol (15 ml), water (11 ml), ethyl acetate (2.0 ml) and aqu. 2N HCl (2.3 ml) was stirred under 1 atmos. pressure of hydrogen until uptake ceased. The mixture was filtered through Hyflo and the filtrate evaporated in vacuo to give the desired product as a pale yellow foam (0.79 g).

Workup

  1. filtrationThe mixture was filtered through Hyflo
  2. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-d5570394e05c4562abb098acd9184903
Source dataset
uspto-grants-1995_11
Patent number
US05466699

Reaction notes

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