Estradiol → Estradiol-dinicate

HRID 260199

反応式

HRID 260199 の反応式
[CH3:1][C@@:2]12[C@@H:18]([OH:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.Cl.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=1>N1C=CC=CC=1>[C:22]([O:20][C:9]1[CH:8]=[CH:7][C:6]2[C@@H:5]3[C@H:14]([C@H:15]4[C@@:2]([CH2:3][CH2:4]3)([CH3:1])[C@@H:18]([O:19][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=3)[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=1

参加物

4

反応物 2

HCID 5757EstradiolHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)

生成物 1

HCID 13731090Estradiol-dinicate収率 90%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Estradiol (2 g, 0.0073 mol) was added to nicotinoyl chloride hydrochloride (5.3 g, 0.029 mol) in dry pyridine (30 ml) at 0° C. The mixture was refluxed for 1 hour and then poured over 100 ml of ice water, filtered and dried over P2O5 under vacuum. Yield 90% (3.18 g), m.p. 148°-150° C. NMR (CDCl3) δ 9.2-9.0 (br s, 2H, C2 pyridinium protons), 8.7-8.3 (m, 2H, C6 pyridinium protons), 8.4-8.0 (m, 2H, C4 pyridinium protons), 7.5-7.1 (m, 3H, C5 pyridinium protons+C1 estradiol proton), 6.9-6.7 (m, 2H, C2,4 estradiol protons), 5.0-4.7 (m, 1H, C17α estradiol proton), 3.2-1.3 (estradiol skeletal protons, 15), 1.0-0.9 (s, 3 H, C18 estradiol protons). IR (KBr) 1750, 1725 cm-1 (2 C=O stretching). Anal. calculated for C30H31N2O4 : C, 74.50; H, 6.47; N, 5.79. Found: C, 74.40; H, 6.32; N, 5.75. The product has the formula: ##STR1471##

後処理

  1. temperatureThe mixture was refluxed for 1 hour
  2. filtrationfiltered
  3. dry with materialdried over P2O5 under vacuum

出典と根拠

ORDレコード
ord-8313516923294c0a8ce5b7262fb265fa
出典データセット
uspto-grants-1996_06
特許番号
US05525727

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