Pyridine → N-(t-butyloxycarbonyl)-4-(n-hexadecylamino)benzoyl-imidazole

反応式

[CH2:1]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].O1CCOCC1.[C:33]([O:37][C:38]([N:40]=[N+]=[N-])=[O:39])([CH3:36])([CH3:35])[CH3:34].[N:43]1[CH:48]=CC=[CH:45][CH:44]=1>>[C:33]([O:37][C:38]([N:40]1[CH:45]=[CH:44][N:43]=[C:48]1[C:22](=[O:24])[C:21]1[CH:20]=[CH:19][C:18]([NH:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:26][CH:25]=1)=[O:39])([CH3:36])([CH3:35])[CH3:34]

参加物

反応物 4

HCID 1049Pyridine

HCID 312751,4-Dioxane

HCID 472634-(Hexadecylamino)benzoic acid

HCID 61256Carbonazidic acid, 1,1-dimethylethyl ester

生成物 1

HCID 20437338N-(t-butyloxycarbonyl)-4-(n-hexadecylamino)benzoyl-imidazole

実験手順

A solution of 10 g. of 4-(n-hexadecylamino)benzoic acid in 100 ml. dioxane is treated with 4.0 g. of t-butylazidoformate and 10 ml. pyridine. After stirring at room temperature for 18 hours, the protected amido-acid is precipitated from solution by addition of 150 ml, of water. The product is collected and thoroughly dried. The crude product is dissolved in 200 ml. of a mixture consisting of methylene chloride/dimethoxy ethane/pyridine (1:4:1), and to this is added 5.4 g. of 1,1'-carbonyldimidazole. The solution is stirred overnight at room temperature and the solvents are evaporated to yield the title compound as a thick, orange oil.