HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → HCID 178450902, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | tert-Butyl 5-(2-tert-butoxy-2-oxoethyl)-3-(2-cyclohexyl-5-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate | HCID 118292862 | — |
| Reactant | HCID 178479379 | HCID 178479379 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Solvent | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Product | HCID 178450902 | HCID 178450902 | 17.4% |
Reaction Steps
4-Carbamimidamidobenzoyl chloride hydrochloride (55.1 mg) was added to a mixture of tert-butyl 5-(2-tert-butoxy-2-oxoethyl)-3-(2-cyclohexyl-5-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate (54.1 mg), pyridine (0.06 mL), and NMP (0.06 mL) at 50 C, and the obtained mixture was stirred at 50 C for 5 days. The reaction mixture was fractionated by HPLC (C18, mobile phase: water/acetonitrile (system containing 0.1% TFA)). To the obtained fraction, a saturated aqueous solution of sodium bicarbonate was added, followed by extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound (12.7 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09428470B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-0a7c6153ed464d148413d661d89b8458 |
| Source note | uspto-grants-2016_08 |