17-Hydroxyprogesterone → Hydroxyprogesterone Impurity 14

HRID 2059164

反応式

HRID 2059164 の反応式
[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]

参加物

6

反応物 3

HCID 623817-HydroxyprogesteroneHCID 24813Phosphorus oxychlorideHCID 517045Sodium Acetate

生成物 1

HCID 11067843Hydroxyprogesterone Impurity 14収率 81.2%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 10024Diethoxymethane溶媒

反応条件

温度
65 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9356e66c12e44ed9ae857b5fded72a1e
出典データセット
uspto-grants-1982_03
特許番号
US04322349

関連ノート

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