HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → Methyl 5-(((1-(tert-butoxycarbonyl)azetidin-3-yl)amino)methyl)thiazole-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Tert-butyl 3-aminoazetidine-1-carboxylate | HCID 1516507 | — |
| Reactant | Methyl 5-(bromomethyl)thiazole-4-carboxylate | HCID 66601492 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 5-(((1-(tert-butoxycarbonyl)azetidin-3-yl)amino)methyl)thiazole-4-carboxylate | HCID 66601525 | 60.5% |
Reaction Steps
A mixture of compound 3b (250 mg, 1.06 mmol), 1-Boc-3-aminoazetidine 1a (310 mg, 1.80 mmol), and K2CO3 (248 mg, 1.80 mmol) in THF (12 mL) was heated to reflux for 6 h. The reaction mixture was cooled to room temperature and diluted with CH2Cl2. The resulting solution was washed with aq. NaHCO3, dried over Na2SO4, and concentrated. Purification by flash column chromatography (silica gel, 3% MeOH/CH2Cl2) gave compound 3c (210 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08759533B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-7ff89c48a55b4992bde5456e47ebe3ce |
| Source note | uspto-grants-2014_06 |