Water → HCID 67924622, compound

HRID 2248843Notes

Reaction equation

HRID 2248843 reaction equation
C([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][CH2:14][C:15]3[C@@:16]4([C:37]#[N:38])[C@:28]([CH3:36])([CH2:29][CH2:30][C:31]=32)[C@@H:19]([C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:18][CH2:17]4)[C:11]1([CH3:40])[CH3:39])(=O)C1C=CC=CC=1.O>[OH-].[K+]>[C:37]([C@:16]12[C:15]3[CH2:14][CH2:13][C@@H:12]4[C@:32]([CH3:35])([CH2:33][CH2:34][C@H:10]([OH:9])[C:11]4([CH3:40])[CH3:39])[C:31]=3[CH2:30][CH2:29][C@:28]1([CH3:36])[C@@H:19]([C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:18][CH2:17]2)#[N:38]

Participants

4

Reactant 2

HCID 962WaterHCID 67924635HCID 67924635, compound2×

Product 1

HCID 67924622HCID 67924622, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

3β-benzoyloxy-14α-cyano-4,4-dimethyl-5α-cholest-8-ene (Compound 16a) (45.3 mg, 83.4 μmol) was dissolved in 1 N ethanolic potassium hydroxide (30 mL) containing 5% water at room temperature. The mixture was stirred for 30 min at 50°, poured into ice water (200 mL) and extracted with dichloromethane (3×200 mL). The combined extracts were dried over anhydrous magnesium sulfate and solvent removed by evaporation under reduced pressure. The residue was subjected to MPLC (80 psi, 50 cm×1.2 cm), using 8% ethyl acetate in toluene as the eluting solvent, to afford 33.0 mg (90%) of Compound 17a.

Workup

  1. extractionextracted with dichloromethane (3×200 mL)
  2. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate and solvent
  3. customremoved by evaporation under reduced pressure

Sources & evidence

ORD record
ord-78c1625421ff45af90eb0480cab444b9
Source dataset
uspto-grants-1991_08
Patent number
US05041432

Reaction notes

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