Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | beta-Phenylisovaleric acid | HCID 13890 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | HCID 70976118 | HCID 70976118 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 70976209 | HCID 70976209 | 51.3% |
Reaction Steps
A solution of 3-methyl-3-phenyl butanoic acid (37.7 mg, 0.212 mmol) and oxalyl chloride (0.024 mL, 0.275 mmol) in dichloromethane (0.80 mL) with a drop of DMF was stirred at room temperature for 90 minutes, concentrated to dryness, and re-dissolved in DCM (0.80 mL). To this solution was added the product from Example 224A (60.6 mg, 0.186 mmol) and pyridine (0.020 mL, 0.248 mmol), and the mixture was stirred at room temperature for 2 hours, concentrated, and chromatographed (2% acetone/DCM) to afford 46.4 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 11.55 (s, 1H), 8.55 (d, J=8.1 Hz, 1H), 8.41 (d, J=7.4 Hz, 1H), 8.16-8.23 (m, 4H), 8.11-8.17 (m, 1H), 8.04 (t, J=7.6 Hz, 1H), 7.40 (d, J=1.7 Hz, 1H), 7.37-7.38 (m, 1H), 7.28-7.34 (m, 2H), 7.19 (t, J=7.2 Hz, 1H), 2.50-2.56 (m, 2H), 1.29 (s, 6H); MS (ESI+) M/Z 487 (M+H)+,504 (M+NH4)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08859549B2 |
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| Source dataset | uspto-grants-2014_10 |
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| ORD ID | ord-323b13336334487fb4480605dfe6c95b |
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| Source note | uspto-grants-2014_10 |
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