Sodium Iodide → 17beta-Acetoxymethoxycarbonyl-3alpha-hydroxy-5alpha-androstan-11-one

HRID 267618

Reaktionsgleichung

Reaktionsgleichung von HRID 267618
[OH:1][C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[C:15](=[O:21])[CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:22]([OH:24])=[O:23])[CH2:3]1.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[I-].[Na+].C(=O)(O)[O-].[K+].[C:50]([O:53][CH2:54]Cl)(=[O:52])[CH3:51]>CC(C)=O>[C:50]([O:53][CH2:54][O:23][C:22]([C@H:11]1[CH2:10][CH2:9][C@H:8]2[C@H:7]3[C@H:16]([C:15](=[O:21])[CH2:14][C@:12]12[CH3:13])[C@:17]1([CH3:20])[C@H:4]([CH2:3][C@H:2]([OH:1])[CH2:19][CH2:18]1)[CH2:5][CH2:6]3)=[O:24])(=[O:52])[CH3:51]

Komponenten

7

Edukt 5

HCID 5238Sodium IodideHCID 69366Chloromethyl acetateHCID 516893Potassium BicarbonateHCID 2723671Tetrabutylammonium HydroxideHCID 227882653alpha-Hydroxy-5alpha-androstan-11-one 17beta-carboxylic acid

Produkt 1

HCID 8673313517beta-Acetoxymethoxycarbonyl-3alpha-hydroxy-5alpha-androstan-11-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

3α-Hydroxy-11-oxo-5α-androstane-17β-carboxylic acid (1g.) was warmed with tetra-butyl ammonium hydroxide (1.94g. Of 40% solution) and acetone (10 ml.) to effect solution. The solution was refluxed with sodium iodide (100 mg.). potassium bicarbonate (150 mg.) and chloromethyl acetate (0.6 ml.) for 2 hours. The mixture was evaporated to small volume, diluted with ethyl acetate, washed with water, dried (Na2SO4) and evaporated to a residue. Purification by preparative t.l.c. gave title compound (less polar band) (318 mg.) as white foam; [α]D + 52°.

Aufarbeitung

  1. customThe mixture was evaporated to small volume
  2. additiondiluted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated to a residue
  6. customPurification by preparative t.l.c

Quellen und Nachweise

ORD-Eintrag
ord-24d9ffb035cb42a5b24446cbd0a21627
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03943124

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