Water → (5R)-3-{4'-[5-(Hydroxymethyl)-4,5-dihydroisoxazol-3-yl]-1,1'-biphenyl-4-yl}-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

HRID 747238Notes

Reaction equation

HRID 747238 reaction equation
[Si]([O:8][CH2:9][CH:10]1[O:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([N:27]4[CH2:31][C@H:30]([CH2:32][N:33]5[CH:37]=[C:36]([CH3:38])[N:35]=[N:34]5)[O:29][C:28]4=[O:39])=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)[CH2:11]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1.C(OCC)(=O)C>[OH:8][CH2:9][CH:10]1[O:14][N:13]=[C:12]([C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:22]=[CH:23][C:24]([N:27]4[CH2:31][C@H:30]([CH2:32][N:33]5[CH:37]=[C:36]([CH3:38])[N:35]=[N:34]5)[O:29][C:28]4=[O:39])=[CH:25][CH:26]=3)=[CH:19][CH:20]=2)[CH2:11]1

Participants

6

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 59749445(5R)-3-{4'-[5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,5-dihydroisoxazol-3-yl]-1,1'-biphenyl-4-yl}-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

Product 1

HCID 59749516(5R)-3-{4'-[5-(Hydroxymethyl)-4,5-dihydroisoxazol-3-yl]-1,1'-biphenyl-4-yl}-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-oneYield 15.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

(5R)-3-{4′-[5-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-4,5-dihydroisoxazol-3-yl]-1,1′-biphenyl-4-yl}-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one (0.2 g, 0.37 mmol) was dissolved in THF (5 ml) at 25° C. Tetrabutylammoniumfluoride.3H2O (0.11 g, 0.40 mmol) was added as a solid and the reaction was stirred at 25° C. for 1.5 hours. The mixture was then diluted with ethyl acetate (50 ml) and poured into water. The layers were separated and the aqueous layer was extracted three times with ethyl acetate (3×50 ml). The organic layers were combined, dried over sodium sulfate and concentrated in vacuo. The resulting yellow oil was purified by silica flash chromatography with 5-10% methanol in dichloromethane as eluent, giving 0.025 g desired product.

Workup

  1. addition3H2O (0.11 g, 0.40 mmol) was added as a solid
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted three times with ethyl acetate (3×50 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting yellow oil was purified by silica flash chromatography with 5-10% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-45c5a3ab4d7b40c3aedf99360d563a42
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

Loading…