Acetone → HCID 53783372, compound

HRID 1065706Notes

Reaction equation

HRID 1065706 reaction equation
[CH3:1][CH2:2][C:3]([NH:5][C@H:6]1[C@H:11]([OH:12])[CH2:10][C@H:9]2[C@H:13]3[C@H:22]([CH2:23][CH2:24][C@:7]12[CH3:8])[C:21]1[CH:20]=[CH:19][C:18]([OH:25])=[CH:17][C:16]=1[CH2:15][CH2:14]3)=[O:4].CC(C)=O.O.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>[OH-].[Na+]>[C:31]([O:25][C:18]1[CH:19]=[CH:20][C:21]2[C@@H:22]3[C@H:13]([C@H:9]4[C@@:7]([CH2:24][CH2:23]3)([CH3:8])[C@@H:6]([NH:5][C:3](=[O:4])[CH2:2][CH3:1])[C@H:11]([OH:12])[CH2:10]4)[CH2:14][CH2:15][C:16]=2[CH:17]=1)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962Water2×HCID 7412Benzoyl chloride2×HCID 54437758HCID 54437758, compound

Product 1

HCID 53783372HCID 53783372, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

17β-Methylacetamido-oestra-1,3,5(10)-triene-3,16α-diol (13.1 g) was dissolved in aqueous sodium hydroxide solution (260 ml; 2 N), acetone (260 ml) and water (260 ml). Benzoyl chloride (6.5 ml) was added and the mixture stirred vigorously for 10 min.; a further 6.5 ml of benzoyl chloride was added and the mixture was stirred vigorously for a further 10 min. Water (5 l) was added and the precipitated product was filtered, washed with water and dissolved in dichloromethane. The dichloromethane solution was washed with water, dried (Na2SO4) and evaporated to give a white froth (6.8 g), which was crystallised from dichloromethane-ether-light petroleum to give impure product (6.0 g). Acidification of the aqueous mother liquors provided unreacted starting material (7.8 g), which was treated as above to give a further quantity of impure product (2.3 g). Recrystallisation of the combined products from dichloromethane-ether afforded an isomeric mixture of 17β-methylacetamido-oestra-1,3,5(10)-triene-3,16α-diol 3-benzoates (4.68 g; 27%).

Workup

  1. stirringthe mixture was stirred vigorously for a further 10 min
  2. filtrationthe precipitated product was filtered
  3. washwashed with water
  4. dissolutiondissolved in dichloromethane
  5. washThe dichloromethane solution was washed with water
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customto give a white froth (6.8 g), which
  9. customwas crystallised from dichloromethane-ether-light petroleum

Sources & evidence

ORD record
ord-ba6bf03a68e44338b2512bd583e29928
Source dataset
uspto-grants-1982_05
Patent number
US04330539

Reaction notes

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