Glycine → [(4-Benzyl-7-hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carbonyl)-amino]-acetic acid
Reaction equation
C(O[C:4]([C:6]1[N:11]=[C:10]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]2[S:19][C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:21][C:8]=2[C:7]=1[OH:28])=[O:5])C.[NH2:29][CH2:30][C:31]([OH:33])=[O:32]>C[O-].[Na+].CO>[CH2:12]([C:10]1[C:9]2[S:19][C:20]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[N:21][C:8]=2[C:7]([OH:28])=[C:6]([C:4]([NH:29][CH2:30][C:31]([OH:33])=[O:32])=[O:5])[N:11]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 4-benzyl-7-hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester (48 mg, 0.12 mmole) and glycine (185 mg, 2.46 mmole) in 0.5 M sodium methoxide/methanol (4.7 ml) was refluxed for 45 h before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (15 ml) and extracted twice with dichloromethane. The remaining aqueous layer was acidified to pH=3 with 1N HCl (3.5 ml). The resulting precipitate was filtered, washed with water and dried in vacuo to give the title compound as a yellow solid (38 mg). 1H NMR (DMSO-d6, 200 MHz): δ=13.13 (br s, 1H), 9.34 (t, 1H, J=6.0 Hz), 8.08 (m, 2H), 7.58 (m, 3H), 7.33 (m, 5H), 4.36 (s, 2H), 4.06 (d, 2H, J=5.8 Hz); MS: (+) m/z 420.29 (M+1), MS: (−) m/z 418.29 (M−1).