HuagongsheHuagongshe Chemistry Print Report · For research reference only
Calcium Carbonate → 2-Phenoxycarbonylamino-6,7-dihydro-4H-thiazolo(5,4-c)pyridine-5-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Calcium Carbonate | HCID 10112 | — |
| Reactant | Phenyl chloroformate | HCID 15891 | — |
| Reactant | tert-butyl 2-amino-4H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridine-5-carboxylate | HCID 11357283 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-Phenoxycarbonylamino-6,7-dihydro-4H-thiazolo(5,4-c)pyridine-5-carboxylic acid tert-butyl ester | HCID 86686032 | 81.6% |
Reaction Steps
39 g calcium carbonate and 36.8 g phenyl chloroformate in 250 mL THF was added to a stirred solution of 50 g 2-amino-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid tert-butyl ester in 1 L THF. The reaction mixture was allowed to stir for 15 h at RT. The reaction mixture was filtered through silica gel and the filtrate was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate and the organic layer was dried over magnesium sulfate. The organic layer was concentrated under reduced pressure. The residue was washed with 20% ethyl acetate in hexane to give 60 g of the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08642774B2 |
| Source dataset | uspto-grants-2014_02 |
| ORD ID | ord-1a701deefd8e4b64a92103bf431b87ed |
| Source note | uspto-grants-2014_02 |