Glycine → [(7-Hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acid
Reaction equation
C(O[C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[S:14][C:8]=2[C:7]=1[OH:21])=[O:5])C.[NH2:22][CH2:23][C:24]([OH:26])=[O:25]>C[O-].[Na+].CO>[OH:21][C:7]1[C:8]2[S:14][C:13]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[N:12][C:9]=2[CH:10]=[N:11][C:6]=1[C:4]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:5]Participants
Procedure
A mixture of 7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (63 mg, 0.21 mmol) and glycine (317 mg, 4.22 mmol) in 0.5 M sodium methoxide/methanol (8 mL) was refluxed for 3 days before it was cooled to room temperature and concentrated in vacuo. Water (20 mL) was added and the suspension was adjusted to pH=10 with 1N HCl (3 mL). The mixture was extracted twice with dichloromethane. And the remaining aqueous layer was acidified to pH=3 with 1N HCl (1.5 mL). The white precipitate was filtered, washed with water and dried in vacuo to give the title compound as a white solid (36 mg): 1H NMR (DMSO-d6, 200 MHz): δ=9.49 (br s, 1H), 8.91 (s, 1H), 8.18 (m, 2H), 7.63 (m, 2H), 4.03 (d, J=5.8 Hz, 2H); MS: (+) m/z 329.9 (M+1)
Workup
- temperaturewas refluxed for 3 days before it
- concentrationconcentrated in vacuo
- additionWater (20 mL) was added
- extractionThe mixture was extracted twice with dichloromethane
- filtrationThe white precipitate was filtered
- washwashed with water
- customdried in vacuo
Sources & evidence
- ORD record
- ord-a5ee4666d5264d9886121959865edef6
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07696223B2
Reaction notes
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