Methanol, 1-methoxy-, 1-acetate → Megestrol Acetate

HRID 325279노트

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HRID 325279 반응식
[C:1]([O-])(=O)C.[Na+].C(OCOC)(=O)C.[C:13]([O:16][C@:17]1([C@:37]2([CH3:38])[C@H:23]([C@H:24]3[C@H:34]([CH2:35][CH2:36]2)[C@:32]2([CH3:33])[C:27](=[CH:28][C:29](=[O:39])[CH2:30][CH2:31]2)[CH2:26][CH2:25]3)[CH2:22][CH2:21]1)[C:18](=[O:20])[CH3:19])(=[O:15])[CH3:14]>C(Cl)(Cl)Cl.P(Cl)(Cl)(Cl)=O>[C:13]([O:16][C@:17]1([C@:37]2([CH3:38])[C@H:23]([C@H:24]3[C@H:34]([CH2:35][CH2:36]2)[C@:32]2([CH3:33])[C:27](=[CH:28][C:29](=[O:39])[CH2:30][CH2:31]2)[C:26]([CH3:1])=[CH:25]3)[CH2:22][CH2:21]1)[C:18](=[O:20])[CH3:19])(=[O:15])[CH3:14]

참가 물질

6

반응물 3

HCID 78087Methanol, 1-methoxy-, 1-acetateHCID 517045Sodium AcetateHCID 10156152Hydroxyprogesterone acetate

생성물 1

HCID 11683Megestrol Acetate수율 61%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 24813Phosphorus oxychloride용매

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온도
70 °C

실험 절차

A suspension of 0.5 g of sodium acetate in 60 ml of anhydrous chloroform and 2 ml of distilled phosphorus oxychloride is refluxed under agitation for 30 minutes at a bath temperature of 70° C. After adding 15 ml of methoxymethyl acetate and 2.0 g of 17α-acetoxy-4-pregnene-3,20-dione, the reaction solution is further stirred for 5 hours at 70° C. Subsequently such an amount of a saturated soda solution is added dropwise at room temperature that the aqueous phase remains alkaline. The organic phase is separated, washed with water, and dried over sodium sulfate. After concentration, the crude product is purified on 100 g of silica gel with a hexane-ethyl acetate gradient (0-50% ethyl acetate), thus isolating 1.26 g of 17α-acetoxy-6-methyl-4,6-pregnadiene-3,20-dione, mp 217°-219° C.

후처리

  1. additionSubsequently such an amount of a saturated soda solution is added dropwise at room temperature that the aqueous phase
  2. customThe organic phase is separated
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationAfter concentration
  6. customthe crude product is purified on 100 g of silica gel with a hexane-ethyl acetate gradient (0-50% ethyl acetate)

출처 및 근거

ORD 기록
ord-7e982a77634d4de386ec7e10a5b70a8e
출처 데이터셋
uspto-grants-1984_04
특허 번호
US04440684

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