Tert-butyl 2-(butylamino)acetate → N2 (6,7-dimethoxy-2-naphthylsulfonly)-L-arginyl-N-butylglycine tert-butyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:13])[CH2:7][NH:8][CH2:9][CH2:10][CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[N:14]#[N:15].[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[O:28][CH3:29])[CH:24]=[C:23]([S:30]([NH:33][C@H:34]([C:42](Cl)=[O:43])[CH2:35][CH2:36][CH2:37][NH:38][C:39](=[NH:41])[NH2:40])(=[O:32])=[O:31])[CH:22]=[CH:21]2>C(Cl)(Cl)Cl>[N:14]#[N:15].[C:1]([O:5][C:6](=[O:13])[CH2:7][N:8]([C:42](=[O:43])[C@H:34]([CH2:35][CH2:36][CH2:37][NH:38][C:39](=[NH:40])[NH2:41])[NH:33][S:30]([C:23]1[CH:22]=[CH:21][C:20]2[C:25](=[CH:26][C:27]([O:28][CH3:29])=[C:18]([O:17][CH3:16])[CH:19]=2)[CH:24]=1)(=[O:32])=[O:31])[CH2:9][CH2:10][CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2]Participants
4
Procedure
To a stirred solution of 2.64 g of N-butylglycine tert-butyl ester in 20 ml of chloroform was carefully added N2 -(6,7-dimethoxy-2-naphthylsulfonyl)-L-arginyl chloride obtained above. The reaction mixture was allowed to stand at room temperature for 1 hour. At the end of this period, the reaction mixture was washed twice with 20 ml of saturated sodium chloride solution and evaporated to dryness. The residue was triturated with a small amount of water to give a crystalline material. This was collected by filtration and recrystallized from ethanol-ethyl ether to give 2.28 g (82 percent) of N2 -(6,7-dimethoxy-2-naphthylsulfonyl)-L-arginyl-N-butylglycine tert-butyl ester, M.P. 164-166° C, I.R. (KBr): 3,390, 3,165, 1,735, 1,370 cm-1.