Acetone → HCID 67582830, compound

HRID 1416490Notes

Reaction equation

HRID 1416490 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:26]=[C:25]([O:27][CH2:28]/C=C/C)[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CC[O:36]CC1.[CH3:40][C:41]([CH3:43])=[O:42]>C(O)(C)(C)C.O.[Os](=O)(=O)(=O)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:26]=[C:25]([O:27][CH2:28][CH:40]([OH:36])[CH:41]([OH:42])[CH3:43])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 67582976HCID 67582976, compound

Product 1

HCID 67582830HCID 67582830, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A mixture of 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[trans-(2-buten-1-yl)oxy]quinazoline (1.30 g), a solution of osmium tetroxide in t-butanol (osmium tetroxide 106 mg/t-butanol 8.36 g) (312 mg) and 4-methylmorpholine N-oxide (382 mg) in water (2 ml)--acetone (15 ml) is stirred at room temperature for 14 hours. Acetone is distilled off from the reaction mixture under reduced pressure, and the resultant product is diluted with ethyl acetate, and the mixture is washed with 10% aqueous sodium sulfite solution and water. The ethyl acetate solution is dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure, and the residue is purified by medium pressure liquid column chromatography (eluent, chloroform:methanol=100:1, v/v) to give 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(2RS,3RS)-(2,3-dihydroxybutan-1-yl)oxy]quinazoline (1.02 g) as foam.

Workup

  1. distillationAcetone is distilled off from the reaction mixture under reduced pressure
  2. additionthe resultant product is diluted with ethyl acetate
  3. washthe mixture is washed with 10% aqueous sodium sulfite solution and water
  4. dry with materialThe ethyl acetate solution is dried over anhydrous magnesium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customthe residue is purified by medium pressure liquid column chromatography (eluent, chloroform

Sources & evidence

ORD record
ord-847f0a895ddf4f6aafb6b73bfe6d1f00
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

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