Pyridine → 4-Methyl-20-(10-undecenoyloxy)-5alpha-4-azapregnan-3-one

HRID 975845노트

반응식

HRID 975845 반응식
[OH:1][CH:2]([C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([N:12]([CH3:24])[C:13](=[O:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1)[CH3:3].N1C=CC=CC=1.[C:31](Cl)(=[O:42])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH:40]=[CH2:41]>C(Cl)Cl>[CH3:24][N:12]1[C:13](=[O:23])[CH2:14][CH2:15][C@@:16]2([CH3:17])[C@H:11]1[CH2:10][CH2:9][C@@H:8]1[C@@H:18]2[CH2:19][CH2:20][C@@:21]2([CH3:22])[C@H:7]1[CH2:6][CH2:5][C@@H:4]2[CH:2]([O:1][C:31](=[O:42])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH:40]=[CH2:41])[CH3:3]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 3804210-Undecenoyl chlorideHCID 2286256620-Hydroxy-4-methyl-5a-4-azapregnan-3-one

생성물 1

HCID 228706344-Methyl-20-(10-undecenoyloxy)-5alpha-4-azapregnan-3-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 20-hydroxy-4-methyl-5α-4-azapregnan-3-one (0.167 g, 0.5 mM) and pyridine (0.1 mL) in anhydrous methylene chloride (4.5 mL) at ice-bath temperatures was added 10-undecenoyl chloride (0.13 mL, 0.6 mM) dropwise. After 10 minutes, the reaction mixture was allowed to warm to room temperature and stir overnight. After diluting further with methylene chloride the mixture was washed with dilute hydrochloric acid, water, and brine, and dried (Na2SO4). The residue obtained from concentration of the filtered solution was flash chromatographed on silica gel using ethyl acetate as eluant to give the title compound as a glaze. MS M+ calculated for C32H53NO3, mw=499.78; observed m/e 499.

후처리

  1. washwas washed with dilute hydrochloric acid, water, and brine
  2. dry with materialdried (Na2SO4)
  3. customThe residue obtained from concentration of the filtered solution
  4. customchromatographed on silica gel

출처 및 근거

ORD 기록
ord-13ffd772ea8b47a4bc11fe96f0b584fc
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05610162

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