Acetone → HCID 67582985, compound

HRID 1416474Notes

Reaction equation

HRID 1416474 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 67582094HCID 67582094, compound

Product 1

HCID 67582985HCID 67582985, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(1R,4S)-(4-hydroxycyclopent-2-en-1-yl)oxy]quinazoline (1.00 g), a solution of osmium tetroxide in t-butanol (osmium tetroxide 252 mg/t-butanol 18.1 g) (409 mg) and 4-methylmorpholine N-oxide (281 mg) in water (2 ml)--acetone (20 ml) is stirred at room temperature for 8 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-[(1R,2R,3R,4S)-(2,3,4-trihydroxycyclopentan-1-yl)oxy]quinazoline (954 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-23039b36f40446449f2901be6b8695f8
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

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