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

HRID 1938927ノート

反応式

HRID 1938927 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ee2a1fe259b84452b59a60094225b6d6
出典データセット
uspto-grants-1997_12
特許番号
US05693809

反応ノート

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