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

HRID 1167485Notes

Reaction equation

HRID 1167485 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:21]2[CH2:25][C@H:24]([CH2:26][OH:27])[O:23][C:22]2=[O:28])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]1.[ClH:29]>C(O)C>[ClH:29].[F:1][C:2]1[CH:3]=[C:4]([N:21]2[CH2:25][C@H:24]([CH2:26][OH:27])[O:23][C:22]2=[O:28])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]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

3-(3-Fluoro-4-(4-t-butoxycarbonylpiperazin-1-yl)phenyl)-5(R)-hydroxymethyloxazolidin-2-one (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, to give a solution. 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 the title product. A further crop was obtained by evaporation of the mother liquors. Total vield: 38.7 g.

Workup

  1. customto give a solution
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with diethyl ether (3×250 ml)
  4. customdried

Sources & evidence

ORD record
ord-97e62611288f4313ba6a44c24147f63a
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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