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

HRID 1460088ノート

反応式

HRID 1460088 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Benzoyl chloride (0.33, 2.3 mmol) was added dropwise to a solution of (±)-4-((αR*)-α-((2S*,5R*)-4-allyl-2,5dimethyl-1-piperazinyl)-3-hydroxybenzyl)-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): δ 0.9 (d, 3H); 1.2 (d, br t, 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); 5.3 (s, 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).

後処理

  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

出典と根拠

ORDレコード
ord-48a627b9fbad4ac7a6ff07399ee1cc4b
出典データセット
uspto-grants-1998_12
特許番号
US05854249

反応ノート

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