Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | HCID 10342788 | HCID 10342788 | — |
| Catalyst | Acetic Acid | HCID 176 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Sodium | HCID 5360545 | — |
| Product | HCID 9998635 | HCID 9998635 | — |
Reaction Steps
To a solution of (2S)-N-(cyanomethyl)-4-methyl-2-[((R)-phenyl{4-[(trimethylsilyl)ethynyl]phenyl}methyl)oxy]pentanamide from example 70 (0.12 mmol, 50 mg) in THF:MeOH (1.3 mL: 50 uL) at 0° C., AcOH (3 drops) was added followed by tetrabutylammonium triphenyldifluorosilicate (0.01 mmol, 7 mg). The mixture was stirred 20 minutes at 0° C. The mixture was diluted with 1% sodium hydroxyde (3 mL) and diethlyl ether (5 mL). The phases were separated. The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. Purification: 30:70 (AcOEt:Hex.) gave the title amide.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07279478B2 |
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| Source dataset | uspto-grants-2007_10 |
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| ORD ID | ord-05c6d29228b84589bd9d3459f96cf058 |
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| Source note | uspto-grants-2007_10 |
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