HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → (2S)-2-{[(Z)-3-cyclohexyl-1-methyl-3-oxo-1-propenyl]amino}-3-{4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl}propanoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | 1-Cyclohexylbutane-1,3-dione | HCID 162099 | — |
| Reactant | (2S)-2-amino-3-{4-[2-(5-methyl-2-phenyl-1,3oxazol-4-yl)ethoxy]phenyl}propanoic acid | HCID 18343040 | — |
| Product | (2S)-2-{[(Z)-3-cyclohexyl-1-methyl-3-oxo-1-propenyl]amino}-3-{4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl}propanoic acid | HCID 70161424 | — |
Reaction Steps
The title compound was prepared (as described above for the preparation of Example 2) from 428 mg (0.89 mmol) of Intermediate 45 (as the TFA salt) and 150 mg (0.89 mmol) of Intermediate 33 to yield 245 mg (53% yield) of Example 43 as a solid beige-colored glass: TLC (DCM/MeOH (4:1): Rf=0.69; 1H NMR (DMSO-d6, 400 MHz) δ10.79 (d, 1H, J=9.0), 7.89 (m, 2H), 7.50-7.41 (m, 3H), 7.05 (d, 2H, J=8.4), 6.77 (d, 2H, J=8.4), 4.7 (s, 1H), 4.12 (t, 2H, J=6.5), 3.9 (br s, 1H), ), 3.04 (dd, 1H, J=13.6, 4.0), 2.87 (t, 2H, J=6.5), 2.64 (dd, 1H, J=13.6, 8.9), 2.32 (s, 3H), 1.9 (m, 1H), 1.6 (m, 4H), 1.5 (s, 3H), 1.25-1.05 (m, 4H): low resolution MS (ES+)m/e 517.3 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06498174B1 |
| Source dataset | uspto-grants-2002_12 |
| ORD ID | ord-4d43fe01a2c3486ab234790809113df4 |
| Source note | uspto-grants-2002_12 |