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

HRID 1109010노트

반응식

HRID 1109010 반응식
[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

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 11142115HCID 11142115, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-24f281f282834b82b37b8887c3fa30d2
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05318961

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