Hydrochloric Acid → HCID 22842945, compound

HRID 2372624Notes

Reaction equation

HRID 2372624 reaction equation
C1O[C:4]2([CH2:21][CH2:20][C@@:19]3([CH3:22])[C:6](=[CH:7][CH2:8][C@@H:9]4[C:18]3=[CH:17][CH2:16][C@@:14]3([CH3:15])[C@H:10]4[CH2:11][C@@H:12]([CH3:35])[C@@H:13]3[C:23](=[O:34])[CH2:24][CH2:25][CH2:26][O:27]C3CCOCC3)[CH2:5]2)[O:3]C1.Cl.C(=O)(O)[O-].[K+]>CC(C)=O>[CH3:35][C@@H:12]1[CH2:11][C@H:10]2[C@H:9]3[C:18](=[CH:17][CH2:16][C@:14]2([CH3:15])[C@H:13]1[C:23](=[O:34])[CH2:24][CH2:25][CH2:26][OH:27])[C@:19]1([CH3:22])[C:6](=[CH:5][C:4](=[O:3])[CH2:21][CH2:20]1)[CH2:7][CH2:8]3

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516893Potassium BicarbonateHCID 86745583HCID 86745583, compound

Product 1

HCID 22842945HCID 22842945, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

16α-Methyl-17β-(1-oxo-[4-tetrahydropyranyloxy]butyl)-androsta-5,9(11)-dien-3-one 3-ethylene ketal, step (D), is dissolved in acetone (90 ml) and hydrochloric acid (1 N, 10 ml) and allowed to stand at 20°-25° for several hours. Following addition of potassium bicarbonate (1 N, 25 ml), the mixture is concentrated and extracted with ethyl acetate. The concentrate is chromatographed on silica gel eluting with acetone/methylene chloride. The appropriate fractions are pooled and concentrated to give 16α-methyl-17β-(1-oxo-[4-hydroxy]butyl)androsta-4,9(11)-dien-3-one.

Workup

  1. waitto stand at 20°-25° for several hours
  2. concentrationthe mixture is concentrated
  3. extractionextracted with ethyl acetate
  4. customThe concentrate is chromatographed on silica gel eluting with acetone/methylene chloride
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7f2bf6ce0ccb4360a952a247ce1060e3
Source dataset
uspto-grants-1992_03
Patent number
US05099019

Reaction notes

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