Water → (5R)-3-[3-fluoro-4-(3-hydroxyazetidin-1-yl)phenyl]-5-(isoxazol-3-yloxymethyl)oxazolidin-2-one

HRID 1167430Notes

Reaction equation

HRID 1167430 reaction equation
[Si]([O:8][CH:9]1[CH2:12][N:11]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][C@H:22]([CH2:24][O:25][C:26]4[CH:30]=[CH:29][O:28][N:27]=4)[O:21][C:20]3=[O:31])=[CH:15][C:14]=2[F:32])[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[OH:8][CH:9]1[CH2:12][N:11]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][C@H:22]([CH2:24][O:25][C:26]4[CH:30]=[CH:29][O:28][N:27]=4)[O:21][C:20]3=[O:31])=[CH:15][C:14]=2[F:32])[CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 699815973-(4-(3-t-Butyldimethylsilyloxy-1-azetidinyl)-3-fluorophenyl)-5(R)-(isoxazol-3-yl-oxymethyl)oxazolidin-2-one

Product 1

HCID 497421(5R)-3-[3-fluoro-4-(3-hydroxyazetidin-1-yl)phenyl]-5-(isoxazol-3-yloxymethyl)oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(4-(3-t-Butyldimethylsilyloxy-1-azetidinyl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxy methyl)oxazolidin-2-one (230 mg, 0.5 mmol) was dissolved in tetrahydrofuran (10 ml), and cooled under nitrogen to 0°. A solution of tetra-n-butylammonium fluoride (1 M, 1 ml, 1 mmol) was added and the mixture allowed to come to ambient temperature. Water (2 ml) was added, and the mixture evaporated to dryness. The residue was purified by chromatography on a 10 g silica Mega Bond Elut(D column, eluting with a gradient increasing in polarity from 0 to 2.5% MeOH in dichloromethane. Relevant fractions were combined and evaporated, then redissolved in EtOAc and the desired product (96 mg) precipitated by addition of isohexane.

Workup

  1. temperaturecooled under nitrogen to 0°
  2. customto come to ambient temperature
  3. customthe mixture evaporated to dryness
  4. customThe residue was purified by chromatography on a 10 g silica Mega Bond Elut(D column
  5. washeluting with a gradient
  6. temperatureincreasing in polarity from 0 to 2.5% MeOH in dichloromethane
  7. customevaporated
  8. dissolutionredissolved in EtOAc
  9. customthe desired product (96 mg) precipitated by addition of isohexane

Sources & evidence

ORD record
ord-3180515d54ea4cb9aa105bf568403dcb
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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