Acetic Acid → Desogestrel

HRID 1446149

반응식

HRID 1446149 반응식
[CH2:1]([C@:3]12[CH2:11][C:10](=[CH2:12])[C@@H:9]3[C@@H:13]4[C:18]([CH2:19][CH2:20][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][CH2:4]2)=[CH:17][CH2:16][CH2:15][CH2:14]4)[CH3:2].[C-]#[C-].[Li+].[Li+].[CH2:25](N)[CH2:26]N.C(O)(=[O:31])C>CS(C)=O.O>[CH3:2][CH2:1][C@@:3]12[C@:4]([OH:31])([C:25]#[CH:26])[CH2:5][CH2:6][C@H:7]1[C@@H:8]1[CH2:20][CH2:19][C:18]3[C@@H:13]([C@H:9]1[C:10](=[CH2:12])[CH2:11]2)[CH2:14][CH2:15][CH2:16][CH:17]=3

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 3301EthylenediamineHCID 86601160HCID 86601160, 화합물2회HCID 178462446HCID 178462446, 화합물

생성물 1

HCID 40973Desogestrel수율 89%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

100 g (0.35 moles) of 13-ethyl-11-methylen-gon-4-ene (compound XVIII) were dissolved in anhydrous dimethylsulfoxide (3 liters) under stirring at room temperature. 430 g of lithium acetylide complexed with ethylendiamine were added to the so obtained solution and the stirring at room temperature was carried on for 21 hours. After this period the reaction was spilled in water cooled at a temperature of 2° C. (3 liters) then a 10% aqueous solution of acetic acid was added (7 liters) and the aqueous phase was extracted with dichloromethane (3×2 liters). The organic extracts were subsequently washed with a saturated solution of sodium bicarbonate (2 liters) and then with a saturated solution of sodium chloride. The organic phase was then dehydrated on sodium sulfate, filtered and evaporated to dryness to give 96.24 g (0.31 moles; yields 89%) of Desogestrel.

후처리

  1. additionwere added to the so obtained solution
  2. customstirring at room temperature
  3. customwas carried on for 21 hours
  4. temperaturecooled at a temperature of 2° C. (3 liters)
  5. extractionthe aqueous phase was extracted with dichloromethane (3×2 liters)
  6. washThe organic extracts were subsequently washed with a saturated solution of sodium bicarbonate (2 liters)
  7. filtrationfiltered
  8. customevaporated to dryness

출처 및 근거

ORD 기록
ord-e0d36b3652984a508820e022f412fb9d
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07667056B2

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