Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HOAt | HCID 181649 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | HCID 10425339 | HCID 10425339 | — |
| Reactant | HCID 86596609 | HCID 86596609 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Diethylether hexane | HCID 21584099 | — |
| Product | HCID 70946002 | HCID 70946002 | — |
Reaction Steps
To (2S)-2-amino-N-[(1S,2E)-3-cyano-1-isopropyl-2-propenyl]-N,3,3-trimethylbutanamide trifluoroacetic acid (179 mg, from Reference Example 16), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 297 mg) and 1-Hydroxy-7-azabenzotriazole (HOAt, 6.8 mg) is added diisopropylethylamine (252 uL) followed by dichloromethane (9 mL) and (2S)-2-[(tert-butoxycarbonyl)(methyl)amino]-3-methyl-3-phenylbutanoic acid (162 mg). After 18 h 5% aqueous citric acid is added. The aqueous phase is washed with dichloromethane three times. The combined organic extracts are dried over anhydrous magnesium sulfate and concentrated in vacuo to give a yellow oil. Chromatography (silica gel, hexane/ether) gave the title compound as a yellow foam (176 mg). MS (ES): m/z 541.1 (M+H)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07626023B2 |
|---|
| Source dataset | uspto-grants-2009_12 |
|---|
| ORD ID | ord-22cb354117f64b2d911b8af0a2a2bd5d |
|---|
| Source note | uspto-grants-2009_12 |
|---|
