Hydrochloric Acid → HCID 135966567, compound

Participants

Reaction Conditions

Reaction Steps

Compound 1B (6.76 g, 20.3 mmoles) was treated with 300 mL of 1:1 ethanol/1.0N sodium hydroxide (V/V) and heated to 40° C. for 5 hours. The solution was treated with concentrated hydrochloric acid to pH 3.5, and the resulting solid was filtered and washed with 3 volumes (30 mL) of water. The solid was dissolved in 0.1N sodium hydroxide (355 mL) and treated dropwise with concentrated hydrochloric acid to pH 6.4 and filtered. The filtrate was further acidified to pH 3.5, refiltered, and the resulting solid was washed with 3 volumes (20 mL) of water and was dried at 50° C. in vacuo to yield 3.57 g (58%) of the title compound, 1C, as a white solid. Anal: Calcd for C14H16N4O4C, 55.26; H 5.29, N 18.41. Found: C 55.34; H, 5.31; N, 18.31. NMR (DMSO-d6) δ 1.8 (m, 2H, CH2 --CH2 --CH2), 2.3 (t, 2H, CH2 --CH2CH2 --O), 4.0 (t, 2H, CH2 --O), 5.7 (s, 2H, NH2), 5.9 (s, 2H, NH2), 9.8 (br s, ring NH), 12.6 (br, 1H, CO2H), 7.0 (d, 2H, benzoic H's ortho to oxygen), 7.85 (d, 2H, benzoic H's ortho to carbonyl). MS: (CI) 305 (M+1), 167 (M-OPhCO2H), 139 (H2OPhCO2H+).

Provenance & Evidence