Benzoyl chloride → (20S)-21-hydroxy-20-methylpregn-4-en-3-one benzoate

HRID 1109010ノート

反応式

HRID 1109010 の反応式
[OH:1][CH2:2][C@@H:3]([CH3:24])[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:11](=[CH:12][C:13](=[O:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.C(N(CC)CC)C.[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl>[C:32]([OH:39])(=[O:1])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[OH:1][CH2:2][C@@H:3]([CH3:24])[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:11](=[CH:12][C:13](=[O:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1

参加物

5

反応物 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 11142115HCID 11142115、化合物

生成物 1

HCID 86745920(20S)-21-hydroxy-20-methylpregn-4-en-3-one benzoate収率 171.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of (20S)-21-hydroxy-20-methylpregn-4-en-3-one (8.0 g, 24.2 mmole) in dichloromethane (200 mL) was cooled in an ice-water bath and treated sequentially with triethylamine (3.69 mL, 26.6 mmole) and benzoyl chloride (3.09 mL, 26.6 mmole) and stirred for 16 hours at room temperature. After the reaction mixture was diluted with dichloromethane (200 mL), it was extracted with ether, dried over magnesium sulfate and filtered and the filtrate was concentrated to a solid which was purified by flash chromatography to give (20S)-21-hydroxy-20-methylpregn-4-en-3-one benzoate (9.4 g, 89.5%) melting at 193°-195° C. after recrystallization from acetone. IR 1716, 1676, 1614 (m), 1284 cm-1 ; MS (CI) 435 (100%, M+1), 313 (70%, M+1--PhCOOH); 1H NMR (CDCl3) δ 0.77 (3H, s, C18 --Me), 1.04 (d, C22 --Me), 1.19 (s, C19 --Me), 4.05 (1H, dd, 1/2 C21 --CH2), 4.34 (1H, dd, 1/2 C21 --CH2), 5.72 (1H, s, C4 --H), 7.45 (2H, t), 7.56 (1H, t), 8.04 (2H, dd).

後処理

  1. extractionwas extracted with ether
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated to a solid which
  5. customwas purified by flash chromatography

出典と根拠

ORDレコード
ord-24f281f282834b82b37b8887c3fa30d2
出典データセット
uspto-grants-1994_06
特許番号
US05318961

反応ノート

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