Acetic Anhydride → HCID 10861689、化合物

HRID 1736640ノート

反応式

HRID 1736640 の反応式
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14]([CH2:15][C@@H:16]([OH:24])[CH2:17][CH2:18]1)=[CH:13][CH2:12]3)([O:3][CH3:4])=[O:2].[C:25](OC(=O)C)(=[O:27])[CH3:26]>N1C=CC=CC=1>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14]([CH2:15][C@@H:16]([O:24][C:25](=[O:27])[CH3:26])[CH2:17][CH2:18]1)=[CH:13][CH2:12]3)([O:3][CH3:4])=[O:2]

参加物

4

反応物 2

HCID 7918Acetic AnhydrideHCID 25186817beta-Carbomethoxyandrost-5-en-3beta-ol

生成物 1

HCID 10861689HCID 10861689、化合物

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a mechanically stirred solution of 17β-carbomethoxy-3β-hydroxy-5-androstene (100 g, 0.30 mol), prepared as described in Rasmusson et al., Journal of Medicinal Chemistry 1984, 27, 1690, incorporated herein by reference, in pyridine (750 mL) in a 2 L 4-necked round bottom flask equipped with an addition funnel at ambient temperature is added acetic anhydride (130 mL, 1.38 mol). The resulting dark solution is stirred at ambient temperature for 18 h, transferred to an addition funnel, and added drop wise to 3 L of ice-water. The resulting precipitate is collected by filtration, washed with 2×1 L H2O, and dried under vacuum to afford 17β-carbomethoxy-3β-acetoxy-5-androstene; 1H NMR (400 MHz, CDCl3) δ5.36 (br d, J=5.1 Hz, 1H), 4.59 (m, 1H), 3.67 (s, 3H), 2.37-2.29 (m, 3H), 2.20-2.08 (m, 1H), 2.03 (s, 3H), 2.02-1.97 (m, 2H), 1.90-1.38 (m, 10H), 1.34-1.21 (m, 2H), 1.18-1.05 m, 2H), 1.02 (s, 3H), 1.00-0.96 (m, 1H), 0.66 (s, 3H).

後処理

  1. customequipped with an addition funnel at ambient temperature
  2. customtransferred to an addition funnel
  3. filtrationThe resulting precipitate is collected by filtration
  4. washwashed with 2×1 L H2O
  5. customdried under vacuum

出典と根拠

ORDレコード
ord-cbda5530e5684dab9325387110561b95
出典データセット
uspto-grants-1996_07
特許番号
US05541322

反応ノート

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