17-Hydroxyprogesterone → Hydroxyprogesterone Impurity 14

HRID 2059164

Reaktionsgleichung

Reaktionsgleichung von HRID 2059164
[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]

Komponenten

6

Edukt 3

HCID 623817-HydroxyprogesteroneHCID 24813Phosphorus oxychlorideHCID 517045Sodium Acetate

Produkt 1

HCID 11067843Hydroxyprogesterone Impurity 14Ausbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 10024DiethoxymethaneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-9356e66c12e44ed9ae857b5fded72a1e
Quelldatensatz
uspto-grants-1982_03
Patentnummer
US04322349

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