Benzoyl chloride → (+/-)-3-((alphaR*)-alpha-((2S*,5R*)-4-allyl-2,5-dimethyl-1-piperazinyl)-4-(diethylcarbamoyl)benzyl)phenyl benzoate

HRID 2258322노트

반응식

HRID 2258322 반응식
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([N:13]1[C@H:18]([CH3:19])[CH2:17][N:16]([C@H:20]([C:28]2[CH:40]=[CH:39][C:31]([C:32]([N:34]([CH2:37][CH3:38])[CH2:35][CH3:36])=[O:33])=[CH:30][CH:29]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=2)[C@@H:15]([CH3:41])[CH2:14]1)[CH:11]=[CH2:12].C(N(CC)CC)C>ClCCl>[C:1]([O:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C@H:20]([N:16]2[CH2:17][C@@H:18]([CH3:19])[N:13]([CH2:10][CH:11]=[CH2:12])[CH2:14][C@@H:15]2[CH3:41])[C:28]2[CH:29]=[CH:30][C:31]([C:32](=[O:33])[N:34]([CH2:35][CH3:36])[CH2:37][CH3:38])=[CH:39][CH:40]=2)[CH:22]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 119029rel-4-((R)-((2S,5R)-2,5-Dimethyl-4-(2-propen-1-yl)-1-piperazinyl)(3-hydroxyphenyl)methyl)-N,N-diethylbenzamide

생성물 1

HCID 57311869(+/-)-3-((alphaR*)-alpha-((2S*,5R*)-4-allyl-2,5-dimethyl-1-piperazinyl)-4-(diethylcarbamoyl)benzyl)phenyl benzoate수율 81.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Benzoyl chloride (0.33 2.3 mmol) was added dropwise to a solution of (±)-4-((αR*)-α-((2S*,5R*)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxy -benzyl)-N,N-diethylbenzamide (0.92 g, 2.1 mmol) (Example 6) and triethylamine (0.60 mL, 4.2 mmol) in 20 mL dichloromethane. The reaction mixture was stirred for 1 hour and then was washed twice with 20 mL of water, dried over sodium sulfate, and concentrated to dryness. The residue was purified by chromatography on silica gel with dichloromethane:ethanol to give 0.92 g (74%) of (±)-3-((αR*)-α-((2S*,5R*)-4-allyl-2,5-dimethyl-1-piperazinyl)-4-(diethylcarbamoyl)benzyl)phenyl benzoate. NMR (300 MHz, CDCl3): δ0.9 (d, 3H); 1.2 (d, brt, 9H); 1.9 (t, J=11 Hz, 1H); 2.1 (dd, 1H); 2.5 (br m, 1H); 2.6 (m, 2H); 2.8 (m, 2H); 3.2-3.6 (br m, 5H); 5.2 (2d, 2H); 5 1H); 5.8 (m, 1H); 7-7.2 (2d, s, 3H); 7.3 (m, 3H); 7.5 (m, 4H); 7.6 (t, 1H), 8.2 (d, 2H).

후처리

  1. washwas washed twice with 20 mL of water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by chromatography on silica gel with dichloromethane

출처 및 근거

ORD 기록
ord-81a2f42d4f504e29b0450253a6e0142c
출처 데이터셋
uspto-grants-1997_08
특허 번호
US05658908

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