Acetone → HCID 67581915, compound

HRID 1416483Notes

Reaction equation

HRID 1416483 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]CC=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:35]CC1.[CH3:39][C:40]([CH3:42])=[O:41]>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][CH2:39][CH:40]([OH:41])[CH2:42][OH:35])[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 67582908HCID 67582908, compound

Product 1

HCID 67581915HCID 67581915, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A mixture of 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(2-propen-1-yl)oxy]quinazoline (1.00 g), a solution of osmium tetroxide in t-butanol (osmium tetroxide 106 mg/t-butanol 8.36 g) (248 mg) and 4-methylmorpholine N-oxide (305 mg) in water (9 ml)--acetone (28 ml) is stirred at room temperature for 21 hours. Acetone is distilled off from the reaction mixture under reduced pressure, and the resultant 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=50:1, v/v) to give 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(RS)-(2,3-dihydroxypropyl)oxy]quinazoline (1.03 g) as crystals.

Workup

  1. distillationAcetone is distilled off from the reaction mixture under reduced pressure
  2. additionthe resultant 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-73b0112feba74baf822230c969fed5f3
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

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