Triethylamine → 3,3-Dimethyl-1-[2-(6-phenylhexanoyl)-perhydropyridazinyl]pentane-1,2-dione

HRID 851946노트

반응식

HRID 851946 반응식
C(N([CH2:6][CH3:7])CC)C.ClC([O:11][CH2:12][CH:13]([CH3:15])C)=O.[CH3:16][C:17]([CH3:30])([CH2:28][CH3:29])[C:18](=[O:27])[C:19]([CH:21]1[CH2:26][CH2:25][CH2:24][NH:23][NH:22]1)=[O:20]>C(Cl)Cl>[CH3:16][C:17]([CH3:30])([CH2:28][CH3:29])[C:18](=[O:27])[C:19]([CH:21]1[CH2:26][CH2:25][CH2:24][NH:23][N:22]1[C:12](=[O:11])[CH2:13][CH2:15][CH2:24][CH2:25][CH2:26][C:7]1[CH:6]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:20]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 694178043,3-Dimethyl-1-perhydropyridazinylpentane-1,2-dione

생성물 1

HCID 184700683,3-Dimethyl-1-[2-(6-phenylhexanoyl)-perhydropyridazinyl]pentane-1,2-dione수율 103.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 5-phenylvalaric acid (0.2 g, 1.1 mmol) in 3 ml CH2Cl2 was added triethylamine (0.15 ml, 1.1 mmol), followed by isobutyl chloroformate (0.15 g, 1.1 mmol) at 0° C. After stirring for 5 minutes, a solution of 3,3-dimethyl-1-perhydropyridazinylpentane-1,2-dione (0.212 g, 1 mmol) in 1 ml CH2Cl2was added. The reaction was gradually warmed up to room temperature. The crude material was subject to silica gel purification to yield final product as clear oil (0.20 g, 55%). Rf=0.58 (33% EtOAc/hexane). 1H NMR (CDCl3, 400 MHz): δ 0.89 (t, 3H, J=7.5); 1.24 (s, 6H); 1.37 (m, 2H); 1.68 (m, 6H); 1.74 (m, 4H); 2.23 (m, 2H); 2.62 (t, 2H, J=7.60); 2.80 (m, 2H); 4.53 (m, 2H); 7.21 (m, 5H). Anal. Calcd. for C23H34N2O3: C, 71.47; H, 8.87; N, 7.25. Found: C, 71.54; H, 8.80; N, 7.32.

후처리

  1. customThe crude material was subject to silica gel purification

출처 및 근거

ORD 기록
ord-13f2ff5661914471aa18f77dbfb39d14
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253169B2

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