Acetone → HCID 59616915, compound

HRID 1471018Notes

Reaction equation

HRID 1471018 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][S:12][CH2:11][CH:10]([C:14]3[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=3)[N:9]2[C:21]2[CH:26]=[CH:25][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.CC(C)=[O:33].C1COCC1.[OH2:40]>[Os](=O)(=O)(=O)=O>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([CH:10]2[CH2:11][S:12](=[O:33])(=[O:40])[CH2:13][CH:8]([C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=3)[N:9]2[C:21]2[CH:26]=[CH:25][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][CH:22]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962Water2×HCID 8028TetrahydrofuranHCID 67236743HCID 67236743, compound

Product 1

HCID 59616915HCID 59616915, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

A solution of Example 159D (850 mg, 1.56 mmol) in mixture of acetone (15 mL), water (5 mL) and THF (5 mL) was added a solution of osmium tetroxide (2.5% in tert-butanol, 0.587 mL, 0.047 mmol) and the mixture was stirred at room temperature for 1.5 hr. The solution was then diluted with water and extracted with EtOAc, the organic extract dried, filtered and concentrated to afford 900 mg (100%) of the title compound. MS (ESI) m/z 578 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. extractionthe organic extract
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-231fb2323fea4208ad66d38d7d723320
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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