Hydrochloric Acid → HCID 22842945, compound

HRID 326493Notes

Reaction equation

HRID 326493 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 (1N, 10 ml) and allowed to stand at 20°-25° for several hours. Following addition of potassium bicarbonate (1N, 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-8541a15f9bc44fadb649e7bddae79731
Source dataset
uspto-grants-1993_12
Patent number
US05268477

Reaction notes

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