3-(4-(4-(2-Phenyl-1,3-dioxan-5-ylcarbonyl)piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one → 3-(4-(4-(3-Hydroxy-2-hydroxymethylpropanoyl)piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one

HRID 1167436Notes

Reaction equation

HRID 1167436 reaction equation
C1(C2[O:12][CH2:11][CH:10]([C:13]([N:15]3[CH2:20][CH2:19][N:18]([C:21]4[CH:26]=[CH:25][C:24]([N:27]5[CH2:31][C@H:30]([CH2:32][O:33][C:34]6[CH:38]=[CH:37][O:36][N:35]=6)[O:29][C:28]5=[O:39])=[CH:23][C:22]=4[F:40])[CH2:17][CH2:16]3)=[O:14])[CH2:9][O:8]2)C=CC=CC=1>C(O)(=O)C.O>[OH:8][CH2:9][CH:10]([CH2:11][OH:12])[C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:31][C@H:30]([CH2:32][O:33][C:34]4[CH:38]=[CH:37][O:36][N:35]=4)[O:29][C:28]3=[O:39])=[CH:23][C:22]=2[F:40])[CH2:17][CH2:16]1)=[O:14]

Participants

4

Reactant 1

HCID 543077073-(4-(4-(2-Phenyl-1,3-dioxan-5-ylcarbonyl)piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one

Product 1

HCID 699804393-(4-(4-(3-Hydroxy-2-hydroxymethylpropanoyl)piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-oneYield 62.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

3-(4-(4-(2-Phenyl-1,3-dioxan-5-ylcarbonyl)piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one (450 mg, 0.82 mmol) was dissolved in a mixture of acetic acid and water (4:1, 10 ml) and stirred at ambient temperature for 18 hours. After evaporation to dryness, the residue was azeotroped with toluene (15 ml), and the residual gum purified by chromatography on a 20 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 5 to 10% MeOH in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (237 mg).

Workup

  1. customAfter evaporation to dryness
  2. customthe residue was azeotroped with toluene (15 ml)
  3. customthe residual gum purified by chromatography on a 20 g silica Mega Bond Elut® column
  4. washeluting with a gradient
  5. temperatureincreasing in polarity from 5 to 10% MeOH in dichloromethane
  6. customevaporated

Sources & evidence

ORD record
ord-f9fe235db3d44b55ba312612fd5889fc
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

Loading…