Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetaldehyde | HCID 177 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | HCID 131735451 | HCID 131735451 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 118061772 | HCID 118061772 | 45% |
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 (82 mg) and acetaldehyde (32 mg) in THF (0.24 mL)/methanol (0.48 mL) was added sodium triacetoxyborohydride (154 mg), and the mixture was stirred at 0° C. for 2 hr. The reaction mixture was 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 (34 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09321757B2 |
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| Source dataset | uspto-grants-2016_04 |
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| ORD ID | ord-f6e8cc00439d4d76b7e94b7c48d8d188 |
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| Source note | uspto-grants-2016_04 |
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