Hydrochloric Acid → HCID 136207632, compound

Participants

Reaction Steps

A sample of compound 1E (0.50 g, 0.99 mmole) was stirred at 50° C. in 0.1N NaOH (18 mL) for 2 hours. The pH was adjusted to 8.0 with 1.0 N HCl and the mixture evaporated to dryness in vacuo. The resulting solid was dissolved in a minimum of ethanol/water (35% ethanol v/v) and chromatographed in 5 injections on a Regis C18 2.1 cm×50 cm, 10 micron, preparative reverse phase column. The combined fractions were reduced in vacuo to 5 mL volume and acidified with concentrated HCl to pH 3.0. Filtration gave a white solid which was dried in vacuo at 50° C. to yield the title compound, 1F, (0.185 g, 41%) as a white powder. Anal: C19H23N5O6S.3/2 H2O: C, 47.89; H, 5.48; N, 14.70. Found: C, 47.99; H, 5.51; N, 14.61. NMR (DMSO-d6) δ1.6 (t, 2H, CH2 --CH2 --CH2), 2.0 (m, 2H, --CH2 --CH2 --CO2H), 2.35 (m, 4H, CH2 --CH2 --CH2 --S and CH2 --CO2H), 2.95 (t, 2H, --CH2 --S), 4.35 (m, 1H, methine), 5.8 (br, 2H, NH2), 6.1 (br, 2H, NH2), 7.3 (d, 2H, phenyl H's ortho to sulfur), 7.75 (d, 2H, phenyl H's ortho to carbonyl), 8.55 (d, 1H, glutamic acid NH), 9.9 (br, 1H, pyrimidine NH), 12.35 (br, 2H, CO2H's).

Provenance & Evidence