HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-Thiazolecarboxylic acid, 2-amino-4-(trifluoromethyl)-, ethyl ester → Ethyl-2-tert-butoxycarbonyloxyamino-4-trifluoromethyl-thiazole-5-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 5-Thiazolecarboxylic acid, 2-amino-4-(trifluoromethyl)-, ethyl ester | HCID 67656 | — |
| Reactant | Di-tert-butyl dicarbonate | HCID 90495 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Ethyl-2-tert-butoxycarbonyloxyamino-4-trifluoromethyl-thiazole-5-carboxylate | HCID 21911370 | 92% |
Reaction Steps
A suspension of ethyl-2-amino-4-trifluoromethyl-thiazole-5-carboxylate (5.05 g, 21.02 mmol), di-t-butyldicarbonate (4.82 g, 22.07 mmol) and 4-dimethylaminopyridine (260 mg, 2.1 mmol) in dichloromethane (209 mL) was stirred under nitrogen for 1.5 h. The solvent was evaporated in vacuo. The residue was chromatographed on a silica gel column. Elution with 5% EtOAc in hexanes, followed by 15% EtOAc in hexanes afforded the title compound (6.57 g, 92%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06979694B2 |
| Source dataset | uspto-grants-2005_12 |
| ORD ID | ord-6be927b5990848c1801e5eedcb26dcd7 |
| Source note | uspto-grants-2005_12 |