Lithium hydroxide, monohydrate → HCID 59378087, compound

Participants

Reaction Steps

A solution of lithium hydroxide monohydrate (0.17 g, 4.05 mmol) in water (5 mL) was added to a stirred solution of 7,7-bis-phenylcarbamoyl-heptanoic acid ethyl ester (16a) (1.07 g, 2.7 mmol) in ethanol (50 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred for 16 hours. The solvent was removed under reduced pressure and the resulting residue was taken up in water (50 mL), washed with ethyl acetate (60 mL) and acidified with 1 M hydrochloric acid. The aqueous layer was extracted with ethyl acetate (3×60 mL), and the combined extracts were dried (MgSO4), filtered and organic solvent evaporated to give 7,7-bis-phenylcarbamoyl-heptanoic acid (16b) as a white solid (0.95 g, 95%); Rf=0.25 (3:1, petroleum ether 60-80° C.:ethyl acetate); 1H NMR (300 MHz, CDCl3): δ 9.83 (2H, s, NH), 7.56 (4H, d, J=7.8 Hz, Ar—H), 7.32 (4H, t, J=8.1 Hz, Ar—H), 7.14 (2H, t, J=7.6 Hz, Ar—H), 3.43 (1H, t, J=7.2 Hz, COCH), 2.58 (2H, t, J=7.1 Hz, CH2CO), 1.86 (2H, br m, CHCH2CH2CH2CH2), 1.49 (2H, t, J=7.1 Hz, CHCH2), 1.33 (4H, br m, CHCH2CH2CH2); 13C NMR (75 MHz, CDCl3): δ 172.10 (CO), 170.17 (CO), 137.13 (quaternary Ar—C), 128.73 (Ar—C—H), 124.68 (Ar—C—H), 120.52 (Ar—C—H), 56.32 (COCH), 34.18 (CH2CO), 33.43 (CHCH2CH2CH2), 28.32 (CHCH2), 27.23 (CHCH2CH2), 24.54 (CHCH2CH2CH2CH2).

Provenance & Evidence