Water → HCID 22795163, Verbindung

HRID 1973737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1973737
Cl[CH2:2][CH2:3][C:4](=[O:26])[C@@H:5]1[C@:22]2([CH3:23])[C@H:8]([C@H:9]3[C@H:19]([C:20](=[O:24])[CH2:21]2)[C@:17]2([CH3:18])[C@H:12]([CH2:13][C@H:14]([OH:25])[CH2:15][CH2:16]2)[CH2:11][CH2:10]3)[CH2:7][CH2:6]1.[C:27]1(=[O:37])[NH:31][C:30](=[O:32])[C:29]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]12.[K].O>CC(C)=O>[OH:25][C@@H:14]1[CH2:15][CH2:16][C@@:17]2([CH3:18])[C@@H:12]([CH2:11][CH2:10][C@@H:9]3[C@@H:19]2[C:20](=[O:24])[CH2:21][C@@:22]2([CH3:23])[C@H:8]3[CH2:7][CH2:6][C@@H:5]2[C:4](=[O:26])[CH2:3][CH2:2][N:31]2[C:27](=[O:37])[C:28]3=[CH:36][CH:35]=[CH:34][CH:33]=[C:29]3[C:30]2=[O:32])[CH2:13]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 24194345Phthalimide potassium saltHCID 8673430721-Chloromethyl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

Produkt 1

HCID 22795163HCID 22795163, VerbindungAusbeute 63,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

21-Chloromethyl-3α-hydroxy-5α-pregnane-11,20-dione (600 mg) in acetone was treated at reflux with potassium phthalimide (600 mg) for 10 hours, poured into water and the oily precipitate extracted into ether. The extracts were washed with water, dried over anhydrous sodium sulphate and evaporated to a white foam (700 mg). Purification by preparative t.l.c. in ethyl acetate/petrol (1:1) gave a foam which on trituration with ether gave title compound (490 mg) as a white solid m.p. 187°-189° [α]D + 58.8° (c = 0.97).

Aufarbeitung

  1. extractionthe oily precipitate extracted into ether
  2. washThe extracts were washed with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated to a white foam (700 mg)
  5. customPurification by preparative t.l.c
  6. customin ethyl acetate/petrol (1:1) gave a foam which on trituration with ether

Quellen und Nachweise

ORD-Eintrag
ord-ce8a375cde5e4420abea5eb96e3232ff
Quelldatensatz
uspto-grants-1976_12
Patentnummer
US03998829

Notizen zur Reaktion

Wird geladen…