Benzhydrylamine → N-diphenylmethyl-3-cyanoandrosta-3,5-diene-17beta-carboxamide

HRID 862278

반응식

HRID 862278 반응식
[C:1]([C:3]1[CH2:20][CH2:19][C@@:18]2([CH3:21])[C:5](=[CH:6][CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:22](O)=[O:23])[CH:4]=1)#[N:2].[C:25]1([CH:31]([NH2:38])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O>C(Cl)Cl>[C:32]1([CH:31]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:38][C:22]([C@H:12]2[CH2:11][CH2:10][C@H:9]3[C@H:8]4[C@H:17]([CH2:16][CH2:15][C@:13]23[CH3:14])[C@:18]2([CH3:21])[C:5]([CH:4]=[C:3]([C:1]#[N:2])[CH2:20][CH2:19]2)=[CH:6][CH2:7]4)=[O:23])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

참가 물질

6

반응물 4

HCID 7036BenzhydrylamineHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 153802543-Cyanoandrosta-3,5-diene-17beta-carboxylic acid

생성물 1

HCID 15380255N-diphenylmethyl-3-cyanoandrosta-3,5-diene-17beta-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

1.0 g of 3-cyanoandrosta-3,5-diene-17β-carboxylic acid [prepared as described in step (b) above], 1.0 ml of diphenylmethylamine and 1.0 ml of triethylamine were dissolved in 10 ml of dry methylene chloride, and 0.75 ml of diethyl cyanophosphate was added to the resulting solution at room temperature. The reaction mixture was stirred at room temperature overnight, after which it was diluted with 100 ml of methylene chloride, and then washed with 1N aqueous hydrochloric acid, with water, with an aqueous solution of sodium hydrogen-carbonate and with a saturated aqueous solution of sodium chloride, in that order. The solution was then dried over anhydrous magnesium sulfate, after which it was concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography through 40 g of silica gel using a gradient elution method, with mixtures of acetone and methylene chloride in ratios ranging from 1:99 to 4:96 by volume as the eluent, to give 0.85 g of the title compound.

후처리

  1. washwashed with 1N aqueous hydrochloric acid, with water, with an aqueous solution of sodium hydrogen-carbonate and with a saturated aqueous solution of sodium chloride, in that order
  2. dry with materialThe solution was then dried over anhydrous magnesium sulfate
  3. concentrationafter which it was concentrated by evaporation under reduced pressure
  4. washa gradient elution method

출처 및 근거

ORD 기록
ord-52ff906006db4e26a0dccd90ca175c9c
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05717088

연결된 노트

불러오는 중…