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

HRID 325279ノート

反応式

HRID 325279 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 11683Megestrol Acetate収率 61%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 24813Phosphorus oxychloride溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7e982a77634d4de386ec7e10a5b70a8e
出典データセット
uspto-grants-1984_04
特許番号
US04440684

反応ノート

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