반응식
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH2:16]([C:20]1[N:21]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:35])[C:22]([CH2:25][CH2:26]O)=[CH:23][N:24]=1)[CH2:17][CH2:18][CH3:19].C(N(C(C)C)CC)(C)C.[CH3:45][O:46][C:47](=[O:57])[C@H:48]([CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[NH2:49]>C(Cl)Cl>[CH3:45][O:46][C:47](=[O:57])[C@H:48]([CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[NH:49][CH2:26][CH2:25][C:22]1[N:21]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:35])[C:20]([CH2:16][CH2:17][CH2:18][CH3:19])=[N:24][CH:23]=1참가 물질
반응물 4
생성물 1
시약·촉매·용매 1
반응 조건
- 온도
- -78 °C
실험 절차
A solution of trifluoromethanesulfonic anhydride (0.954 g, 3.38 mmol) in methylene chloride (5 ml) was cooled to -78° C. under nitrogen, and a solution of 2-n-butyl-1-(2-chlorophenyl)methyl-5-(2-hydroxyethyl)-1H-imidazole (0.9 g, 3.07 mmol), diisopropylethylamine (0.44 g. 3.38 mmol) and methylene chloride (10 ml) was added dropwise. The mixture was stirred at -78° C. for an additional 15 minutes, then a solution of the free base of phenylalanine methyl ester (prepared from 1.33 q (6.15 mmol) of the hydrochloride salt) in methylene chloride (10 ml) was added. This mixture was stirred for 2 hours at -78° C. and an additional 18 hours at ambient temperature. The reaction mixture was washed with water, dried and concentrated and the crude product was flash chromatographed with 5% methanol in ethyl acetate to yield 0.9 g (65%) of N-[2-{1-[(2 chlorophenyl)methyl]-2-n-butyl-1H-imidazol-5-yl}ethyl ]phenylalanine methyl ester.
후처리
- stirringThis mixture was stirred for 2 hours at -78° C. and an additional 18 hours at ambient temperature
- washThe reaction mixture was washed with water
- customdried
- concentrationconcentrated
- customchromatographed with 5% methanol in ethyl acetate
출처 및 근거
- ORD 기록
- ord-50dfb916fc1b4933aac44bd6fca31f18
- 출처 데이터셋
- uspto-grants-1993_09
- 특허 번호
- US05248689
연결된 노트
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