Water → 17beta-[N-(Diphenylmethyl)carbamoyl]androsta-3,5-diene-3-carboxylic acid

HRID 1735547Notes

Reaction equation

HRID 1735547 reaction equation
O.[OH-].[K+].[C:4]1([CH:10]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[NH:11][C:12]([C@H:14]2[CH2:19][CH2:18][C@H:17]3[C@H:20]4[C@H:30]([CH2:31][CH2:32][C@:15]23[CH3:16])[C@:28]2([CH3:29])[C:23]([CH:24]=[C:25]([C:33]([O:35]C)=[O:34])[CH2:26][CH2:27]2)=[CH:22][CH2:21]4)=[O:13])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[C:4]1([CH:10]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[NH:11][C:12]([C@H:14]2[CH2:19][CH2:18][C@H:17]3[C@H:20]4[C@H:30]([CH2:31][CH2:32][C@:15]23[CH3:16])[C@:28]2([CH3:29])[C:23]([CH:24]=[C:25]([C:33]([OH:35])=[O:34])[CH2:26][CH2:27]2)=[CH:22][CH2:21]4)=[O:13])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 15380280Methyl 17beta-[N-(diphenylmethyl)carbamoyl]androsta-3,5-diene-3-carboxylate

Product 1

HCID 1538025617beta-[N-(Diphenylmethyl)carbamoyl]androsta-3,5-diene-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10 ml of water and 1 g of potassium hydroxide were added to a solution of 25 ml of methanol containing 214 mg of methyl 17β-(N-diphenylmethylcarbamoyl)androsta-3,5-diene-3-carboxylate (prepared as described in Example 27). The reaction mixture was then heated under reflux for 4 hours. At the end of this time, methanol from the reaction mixture was removed by distillation under reduced pressure. The mixture was then made acidic by the addition of 1N aqueous hydrochloric acid and extracted with methylene chloride three times. The combined organic extracts were washed with water and with a saturated aqueous solution of sodium chloride, in that order, dried over anhydrous magnesium sulfate, and concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography using 20 g of silica gel and using a gradient elution method, with mixtures of acetone and methylene chloride in ratios ranging from 2:98 to 50:50 by volume as the eluent, to give 110 mg of the title compound.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureunder reflux for 4 hours
  3. customAt the end of this time, methanol from the reaction mixture was removed by distillation under reduced pressure
  4. additionmade acidic by the addition of 1N aqueous hydrochloric acid
  5. extractionextracted with methylene chloride three times
  6. washThe combined organic extracts were washed with water and with a saturated aqueous solution of sodium chloride, in that order
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated by evaporation under reduced pressure
  9. washa gradient elution method

Sources & evidence

ORD record
ord-8f5fdb9fee03461294b4a66aa545e855
Source dataset
uspto-grants-1996_07
Patent number
US05536714

Reaction notes

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