Acetone → HCID 69108330, compound

HRID 1921679Notes

Reaction equation

HRID 1921679 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:30])[NH:17][CH:18]3[CH2:23][CH2:22][CH:21]([C:24]4([CH3:29])OCC[O:25]4)[CH2:20][CH2:19]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.CC(C)=O>O>[C:24]([CH:21]1[CH2:20][CH2:19][CH:18]([NH:17][C:16](=[O:30])[O:15][CH2:14][CH:12]2[C:13]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:6]3[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:23][CH2:22]1)(=[O:25])[CH3:29]

Participants

5

Reactant 3

HCID 180AcetoneHCID 6101p-Toluenesulfonic acidHCID 69108703HCID 69108703, compound

Product 1

HCID 69108330HCID 69108330, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

13.10 g (32 mmol) of 9H-fluoren-9-ylmethyl[4-(2-methyl-[1,3]dioxolan-2-yl)cyclohexyl]carbamate (cis/trans mixture) and 1.30 g of p-toluenesulfonic acid are refluxed in 25 mL of water and 500 mL of acetone for 16 hours with stirring. Then the reaction mixture is concentrated by evaporation and the residue is dissolved in ethyl acetate and extracted with water. The organic phase is dried and evaporated to dryness. The residue is extracted with diisopropylether and suction filtered. Yield: 7.77 g (89%) of cis compound; NMR: LH201628.

Workup

  1. concentrationThen the reaction mixture is concentrated by evaporation
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. extractionextracted with water
  4. customThe organic phase is dried
  5. customevaporated to dryness
  6. extractionThe residue is extracted with diisopropylether and suction
  7. filtrationfiltered

Sources & evidence

ORD record
ord-1f4bd5d1190847569076feb6a4632be3
Source dataset
uspto-grants-2012_05
Patent number
US08173699B2

Reaction notes

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