Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetaldehyde | HCID 177 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 131735451 | HCID 131735451 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 118061332 | HCID 118061332 | — |
Reaction Steps
To a solution of tert-butyl (4-(4-((3-((4S)-4-amino-2-oxopyrrolidin-1-yl)-1-methyl-1H-pyrazol-4-yl)carbamoyl)-1,3-oxazol-2-yl)pyridin-2-yl)(2,2,2-trifluoroethyl)carbamate (42 mg) in THF (1.0 mL) was added acetaldehyde (37 μL), and the mixture was stirred overnight at room temperature. Sodium borohydride (28 mg) and methanol (0.20 mL) were added thereto, and the mixture was stirred at room temperature for 1 hr, and concentrated under reduced pressure. The residue was dissolved in TFA (0.70 mL), and the solution was stirred at room temperature for 20 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate), and recrystallized from ethyl acetate/hexane to give the title compound (14 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09321757B2 |
|---|
| Source dataset | uspto-grants-2016_04 |
|---|
| ORD ID | ord-212e3e42f2d14863aeda2b699d415e7e |
|---|
| Source note | uspto-grants-2016_04 |
|---|