Hydrochloric Acid → 3-(3-Fluoro4-(piperazin-1-yl)phenyl)-5(R)-hydroxymethyloxazolidin-2-one hydrochloride

HRID 1167420Notes

Reaction equation

HRID 1167420 reaction equation
[OH:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)=[C:11]([F:28])[CH:10]=2)[CH2:4]1.[ClH:29]>C(O)C>[ClH:29].[OH:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]3)=[C:11]([F:28])[CH:10]=2)[CH2:4]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 16203632(r)-Tert-butyl 4-(2-fluoro-4-(5-(hydroxymethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate

Product 1

HCID 213565653-(3-Fluoro4-(piperazin-1-yl)phenyl)-5(R)-hydroxymethyloxazolidin-2-one hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

5(R)-hydroxymethyl-3-(3-fluoro-4-(4-t-butoxycarbonylpiperazin-1-yl)phenyl)oxazolidin-2-one (International Patent Application Publication WO 93/23384. 43.1 g, 0.11 M) was suspended by stirring in ethanol (1000 ml) under nitrogen. An ethanol solution of hydrogen chloride (3.8 M, 400 ml) was added slowly, and the mixture was stirred at ambient temperature for 18 hours. The resulting precipitate was filtered, washed with diethyl ether (3×250 ml), and dried, to give 5(R)-hydroxymethyl-3-(3-fluoro-4-(piperazin-1-yl)phenyl)oxazolidin-2-one hydrochloride. A further crop was obtained by evaporation of the mother liquors to give a total yield of 38.7 g.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with diethyl ether (3×250 ml)
  3. customdried

Sources & evidence

ORD record
ord-f9460f7b562d451691e56d690de01e04
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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