Sodium Bicarbonate → 11beta-Chloroacetoxy-3alpha-hydroxy-5alpha-pregnan-20-one

HRID 1701458노트

반응식

HRID 1701458 반응식
C(=O)(O)[O-].[Na+].ClCC([O:10][C@@H:11]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C@@H:13]([CH2:14][CH2:15][C@@H:16]3[C@@H:27]2[C@@H:26]([O:32][C:33](=[O:36])[CH2:34][Cl:35])[CH2:25][C@@:24]2([CH3:37])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[C:21](=[O:23])[CH3:22])[CH2:12]1)=O>CO>[Cl:35][CH2:34][C:33]([O:32][C@H:26]1[CH2:25][C@@:24]2([CH3:37])[C@@H:17]([CH2:18][CH2:19][C@@H:20]2[C:21](=[O:23])[CH3:22])[C@H:16]2[C@H:27]1[C@:28]1([CH3:31])[C@@H:13]([CH2:14][CH2:15]2)[CH2:12][C@H:11]([OH:10])[CH2:30][CH2:29]1)=[O:36]

참가 물질

4

반응물 2

HCID 516892Sodium BicarbonateHCID 867368843alpha,11beta-Bischloroacetoxy-5alpha-pregnan-20-one

생성물 1

HCID 8673686911beta-Chloroacetoxy-3alpha-hydroxy-5alpha-pregnan-20-one수율 78.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Saturated sodium bicarbonate solution (200 ml) was added slowly to a stirred refluxing solution of 3α,11β-bischloroacetoxy-5α-pregnan-20-one (89 g) in methanol (1800 ml). After about 3.5 hours the mixture was evaporated to half its volume, water was added and the steroid was extracted with ethyl acetate. The washed and dried extract was evaporated in vacuo, the residue was filtered through a short column of silica in ethyl acetate-petroleum ether (1:1) and crystallised from ethyl acetate-petroleum ether to afford title compound (59 g), m.p. 83°-86°, [α]D +101° (c 1.0).

후처리

  1. customAfter about 3.5 hours the mixture was evaporated to half its volume, water
  2. additionwas added
  3. extractionthe steroid was extracted with ethyl acetate
  4. washThe washed
  5. customdried
  6. extractionextract
  7. customwas evaporated in vacuo
  8. filtrationthe residue was filtered through a short column of silica in ethyl acetate-petroleum ether (1:1)
  9. customcrystallised from ethyl acetate-petroleum ether

출처 및 근거

ORD 기록
ord-a689ca136b554e0e8cbda14410413f79
출처 데이터셋
uspto-grants-1980_03
특허 번호
US04192871

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