Ethyl Acetate → HCID 178430657, compound

Reaction equation

[NH2:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:7]=[N:8][C:4]=2[C:3]=1[CH3:18].C([N:21]=[C:22](S)[N:23](C(OCC1C=CC=CC=1)=O)[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])C.[C:45]([O:48][CH2:49][CH3:50])(=[O:47])C>O1CCCC1>[C:12]([O:11][C:9]([N:6]1[C:5]2[CH:16]=[CH:17][C:2]([NH:1][C:22]([NH:23][C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])=[N:21][C:45]([O:48][CH2:49][C:50]3[CH:16]=[CH:17][CH:2]=[CH:3][CH:4]=3)=[O:47])=[C:3]([CH3:18])[C:4]=2[N:8]=[CH:7]1)=[O:10])([CH3:13])([CH3:14])[CH3:15]

Participants

Procedure

To a solution of 500 mg of 5-amino-1-(tert-butoxycarbonyl)-4-methyl-benzimidazole in 20 mL of tetrahydrofuran are added 753 mg of ethyl N,N-bis(benzyloxycarbonyl)pseudothiourea and 645 mg of mercuric acetate and the mixture is stirred at room temperature for 1 hour. The resulting suspension is diluted with ethyl acetate and washed with water followed by brine. The aqueous layers are extracted with ethyl acetate; the combined organic layers are dried over magnesium sulfate, filtered and rotary evaporated. The residue is purified by flash column chromatography on silica gel, eluting with 50% ethyl acetate/hexanes followed by recrystallization from hexanes/methylene chloride to provide 927 mg of 1-(tert-butyloxycarbonyl)-5-[N2, N3-bis(benzyloxycarbonyl)-guanidino]-4-methylbenzimidazole as a white solid.