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

HRID 962673ノート

反応式

HRID 962673 の反応式
[C:1]1([CH:7]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[NH:8][C:9]([C@H:11]2[CH2:16][CH2:15][C@H:14]3[C@H:17]4[C@H:27]([CH2:28][CH2:29][C@:12]23[CH3:13])[C@:25]2([CH3:26])[C:20]([CH:21]=[C:22]([C:30]#N)[CH2:23][CH2:24]2)=[CH:19][CH2:18]4)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:38].[K+].Cl.[OH2:41]>C(O)CO>[C:32]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH:8][C:9]([C@H:11]2[CH2:16][CH2:15][C@H:14]3[C@H:17]4[C@H:27]([CH2:28][CH2:29][C@:12]23[CH3:13])[C@:25]2([CH3:26])[C:20]([CH:21]=[C:22]([C:30]([OH:41])=[O:38])[CH2:23][CH2:24]2)=[CH:19][CH2:18]4)=[O:10])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 15380255N-diphenylmethyl-3-cyanoandrosta-3,5-diene-17beta-carboxamide

生成物 1

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

試薬・触媒・溶媒 1

HCID 174Ethylene Glycol溶媒

実験手順

0.8 g of N-diphenylmethyl-3-cyanoandrosta-3,5-diene-17β-carboxamide [prepared as described in step (c) above] and 6.0 g of potassium hydroxide were dissolved in a mixture of 14 ml of water and 20 ml of ethylene glycol, and then the mixture was heated under reflux for 16 hours. At the end of this time, the reaction mixture was cooled to room temperature and made acidic by the addition of dilute aqueous hydrochloric acid. The mixture was then extracted three times with methylene chloride. The combined organic extracts were washed with water and with a saturated aqueous solution of sodium chloride, in that order and dried over anhydrous magnesium sulfate. The mixture was then concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography through 35 g of silica gel using a gradient elution method, with mixtures of acetone and methylene chloride in ratios ranging from 2:98 to 12:88 by volume as the eluent, to give 650 mg of the title compound.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 hours
  3. extractionThe mixture was then extracted three times with methylene chloride
  4. washThe combined organic extracts were washed with water and with a saturated aqueous solution of sodium chloride, in that order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe mixture was then concentrated by evaporation under reduced pressure
  7. washa gradient elution method

出典と根拠

ORDレコード
ord-5e2fb3b70ace4b169a3cf11810ef6397
出典データセット
uspto-grants-1998_06
特許番号
US05760025

反応ノート

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