Sodium Carbonate → HCID 53708079, compound

HRID 1957033Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:19])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[NH2:6])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[CH3:26][C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([CH3:36])[CH:35]=1)[C:30](Cl)=[O:31].CCCCCC.C(OCC)(=O)C>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:19])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[NH:6][C:30](=[O:31])[C:29]1[CH:33]=[C:34]([CH3:36])[CH:35]=[C:27]([CH3:26])[CH:28]=1)[CH3:2]

Participants

Conditions

Temperature: 10 °C

Procedure

Crude 3-[4-(5-isoxazolyl)-phenyl]-alanine ethyl ester (660 mg) is dissolved in chloroform (6.6 ml), stirred vigorously with 2N aqueous sodium carbonate (1,4 ml), and after cooling to 10° C., 3,5-dimethylbenzoylchloride (0.7 ml) is added. Stirring is continued for 1 hour at 10° C. and for 2 hours at ambient temperature. Then extraction with dichloromethane/water, washing with 10% aqueous citric acid, and with brine, followed by evaporation gives the crude product. Flash chromatography on silica gel, hexane/ethyl acetate (4:1), gives pure N-(3,5-dimethylbenzoyl)-3-[4-(5-isoxazolyl)-phenyl]-alanine ethyl ester. NMR (CDCl3, 400 MHz) δ [ppm] 8.28 (d, 1.8 Hz, 1H), 7.72 (d, 8.2 Hz, 2H), 7.33 (s, 2H), 7.26 (d, 8.2 Hz, 2H), 7.15 (s, 1H), 6.65 (d, 7.3 Hz, 1H), 6.50 (d, 1.8 Hz, 1H), 5.09 (m, 1H), 4.24 (q, 7.1 Hz, 2H), 3.32 (m, 2H), 2.34 (s, 6H), 1.29 (t, 7.1 Hz, 3H).

Workup

extractionThen extraction with dichloromethane/water
washwashing with 10% aqueous citric acid
customwith brine, followed by evaporation
customgives the crude product

Sources & evidence

ORD record: ord-2bcb9dee3c834d11b1df58d0ee268f4d
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05780498

Reaction notes

Loading…