HuagongsheHuagongshe Chemistry Print Report · For research reference only
Glycine → [(7-Hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Glycine | HCID 750 | — |
| Reactant | 7-Hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester | HCID 68426358 | — |
| Solvent | Sodium methanolate methanol | HCID 23694274 | — |
| Product | [(7-Hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carbonyl)-amino]-acetic acid | HCID 24756983 | 52.1% |
Reaction Steps
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)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07696223B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-a5ee4666d5264d9886121959865edef6 |
| Source note | uspto-grants-2010_04 |