Acetic Anhydride → HCID 10861689, 화합물

HRID 1736640노트

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HRID 1736640 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 10861689HCID 10861689, 화합물

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cbda5530e5684dab9325387110561b95
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05541322

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