Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl formate | HCID 8025 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 86607899 | HCID 86607899 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 57848919 | HCID 57848919 | 58% |
Reaction Steps
To a solution of 0.15 g (0.28 mmol) of (3S,4R)-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)piperidine-3-carboxamide (Example 47, Step 8) in methanol (0.5 mL) was added ethyl formate (3 mL) followed by diisopropylethylamine (0.2 mL, 1.1 mmol). The reaction mixture was stirred at 48° C. for 18 h and concentrated. The residue was purified using silica chromatography, eluting with a gradient of 1-5% MeOH/CH2Cl2 to afford (3S,4R)-N-tert-butoxy-1-formyl -3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)piperidine-3-carboxamide (0.092 g, 58%). MS: 569.1 (M+H)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07595327B2 |
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| Source dataset | uspto-grants-2009_09 |
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| ORD ID | ord-3736ee6f92084fefadb230ccd587e997 |
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| Source note | uspto-grants-2009_09 |
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