Acetone → HCID 67582894, compound

HRID 1416469Notes

Reaction equation

HRID 1416469 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][C@H]3C[C@@H](O)C=C3)[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:38]CC1.C[C:43]([CH3:45])=[O:44].[C:46]([OH:50])([CH3:49])([CH3:48])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][C@H:45]3[CH2:49][C@@H:46]([OH:50])[C@H:48]([OH:38])[C@@H:43]3[OH:44])[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 4

HCID 180AcetoneHCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 67582038HCID 67582038, compound

Product 1

HCID 67582894HCID 67582894, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(1S,4R)-(4-hydroxycyclopent-2-en-1-yl)oxy]quinazoline (1.30 g), a solution of osmium tetroxide in t-butanol (osmium tetroxide 252 mg/t-butanol 18.1 g) (532 mg) and 4-methylmorpholine N-oxide (375 mg) in water (3 ml)--acetone (25 ml) is stirred at room temperature for 17 hours. Acetone is distilled off from the reaction mixture under reduced pressure, and to the resultant is added 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, 10:1, v/v) to give 2-[4-(benzyloxycarbonyl) piperazin-1-yl]-4-[(1S,2S,3S,4R)-(2,3,4-trihydroxycyclopentan-1-yl)oxy]quinazoline (1.05 mg) as foam.

Workup

  1. distillationAcetone is distilled off from the reaction mixture under reduced pressure
  2. additionto the resultant is added 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-406e7175fe7640168833f420db5495f4
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

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