17-Hydroxyprogesterone → Hydroxyprogesterone Impurity 14

HRID 2059164

반응식

HRID 2059164 반응식
[C:1]([O-])(=O)C.[Na+].P(Cl)(Cl)(Cl)=O.[CH3:11][C:12]([C@:14]1([OH:34])[C@@:18]2([CH3:33])[CH2:19][CH2:20][C@@H:21]3[C@:31]4([CH3:32])[C:25](=[CH:26][C:27]([CH2:29][CH2:30]4)=[O:28])[CH2:24][CH2:23][C@H:22]3[C@@H:17]2[CH2:16][CH2:15]1)=[O:13]>C(Cl)(Cl)Cl.C(OCOCC)C>[OH:34][C@:14]1([C@:18]2([CH3:33])[C@H:17]([C@H:22]3[C@H:21]([CH2:20][CH2:19]2)[C@:31]2([CH3:32])[C:25](=[CH:26][C:27](=[O:28])[CH2:29][CH2:30]2)[C:24](=[CH2:1])[CH2:23]3)[CH2:16][CH2:15]1)[C:12](=[O:13])[CH3:11]

참가 물질

6

반응물 3

HCID 623817-HydroxyprogesteroneHCID 24813Phosphorus oxychlorideHCID 517045Sodium Acetate

생성물 1

HCID 11067843Hydroxyprogesterone Impurity 14수율 81.2%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 10024Diethoxymethane용매

반응 조건

온도
65 °C

실험 절차

A suspension of 1.0 g of sodium acetate in 30 ml of chloroform, 30 ml of formaldehyde diethylacetal, and 3.8 ml of phosphorus oxychloride is agitated in a two-necked flask for 1 hour at a bath temperature of 65° C. and then combined with 1.0 g of 17α-hydroxyprogesterone. The mixture is stirred for 1.5 hours at 65° C., cooled to room temperature, and under vigorous agitation a saturated soda solution is added dropwise until alkaline reaction occurs. The organic phase is separated, washed neutral with water, dried over sodium sulfate, and concentrated under vacuum. The crude product is purified on 220 g of silica gel with a methylene chloride/acetone gradient (0-12% acetone), thus obtaining 842 mg of 17α-hydroxy-6-methylene-4-pregnene-3,20-dione, mp 218°-220° C.

후처리

  1. stirringThe mixture is stirred for 1.5 hours at 65° C.
  2. temperaturecooled to room temperature
  3. additionunder vigorous agitation a saturated soda solution is added dropwise until alkaline reaction
  4. customThe organic phase is separated
  5. washwashed neutral with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe crude product is purified on 220 g of silica gel with a methylene chloride/acetone gradient (0-12% acetone)

출처 및 근거

ORD 기록
ord-9356e66c12e44ed9ae857b5fded72a1e
출처 데이터셋
uspto-grants-1982_03
특허 번호
US04322349

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