Water → HCID 69404092, compound

Reaction equation

[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:42])[NH:17][CH2:18][C:19]3[N:20]([CH2:38][CH:39]([CH3:41])[CH3:40])[C:21](=[O:37])[C:22]4[C:27]([C:28]=3[O:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:26][C:25]([C:34]([NH2:36])=[S:35])=[CH:24][CH:23]=4)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[CH2:44][C:45](=O)[C:46]([O:48][CH2:49][CH3:50])=[O:47].O>C(O)C>[CH2:30]([O:29][C:28]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:34]3[S:35][CH:44]=[C:45]([C:46]([O:48][CH2:49][CH3:50])=[O:47])[N:36]=3)[CH:26]=2)[C:21](=[O:37])[N:20]([CH2:38][CH:39]([CH3:41])[CH3:40])[C:19]=1[CH2:18][NH:17][C:16]([O:15][CH2:14][CH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)=[O:42])[CH2:31][CH2:32][CH3:33]

Participants

Procedure

A solution of 9H-fluoren-9-ylmethyl[6-(aminocarbothioyl)-4-butoxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.29 g, 0.5 mmol) and ethyl bromopyruvate (0.19 g, 1 mmol) in ethanol (10 ml) was refluxed under heating for 1 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from ethyl acetate-diisopropyl ether to give ethyl 2-[4-butoxy-3-[[[(9H-fluoren-9-ylmethoxy)carbony]amino]methyl]-2-isobutyl-1-oxo-1,2-dihydro-6-isoquinolinyl]-1,3-thiazole-4-carboxylate (0.30 g, 90.9%) as crystals.