Water → HCID 10451895, compound

HRID 1452584Notes

Reaction equation

HRID 1452584 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:11]=[CH:12][N:13]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:25][C@H:24]([CH2:26][N:27]4[CH:31]=[C:30]([CH3:32])[N:29]=[N:28]4)[O:23][C:22]3=[O:33])=[CH:17][C:16]=2[F:34])[CH:14]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[F:34][C:16]1[CH:17]=[C:18]([N:21]2[CH2:25][C@H:24]([CH2:26][N:27]3[CH:31]=[C:30]([CH3:32])[N:29]=[N:28]3)[O:23][C:22]2=[O:33])[CH:19]=[CH:20][C:15]=1[N:13]1[CH:14]=[C:10]([CH2:9][OH:8])[N:11]=[CH:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 57526992HCID 57526992, compound2×

Product 1

HCID 10451895HCID 10451895, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(5R)-3-{4-[4-(tert-Butyl(dimethyl)silyloxymethyl)-1H-imidazol-1-yl]-3-fluorophenyl}-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one (Intermediate 31) (1.4 g, 2.88 mmol) was dissolved in tetrahydrofuran (15 ml), and tetrabutylammonium fluoride (3.2 ml, 1.0 M solution in THF) was added. The solution was stirred for 2 hours at room temperature and water (50 ml) was added. The precipitate was collected by filtration and purified by chromatography on silica gel with 3-6% methanol in dichloromethane to give the title compound (0.36 g).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. custompurified by chromatography on silica gel with 3-6% methanol in dichloromethane

Sources & evidence

ORD record
ord-1f9fdffc55c740c78c0aacd8950513f6
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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