Hydrochloric Acid → HCID 14973524, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, allyl 3-(benzyloxycarbonyl)-7-(R,S)-[2-(2-(allyloxycarbonylamino)thiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-8-oxo-1,5-diazabicyclo[3,3.0]octa-2-ene-2-carboxylate (340 mg, 0.54 mmol) was suspended in a mixture of acetonitrile (10 ml) and diethyl ether (5 ml) then palladium(II) acetate (6.1 mg, 0.027 mmol,) and triphenylphosphine (56.7 mg, 0.216 mmol,) were added. Acetone (20 ml) was added and the resultant solution was stirred for 30 minutes at room temperature then cooled to 0° C. Tri(n-butyl)tin hydride (0.3 ml, 1.1 mmol) was added and the solution was stirred for 1.5 hours at room temperature. 12N hydrochloric acid (0.09 ml, 1.1 mmol) was added and the solution was concentrated in vacuo. The resultant residue was dissolved in methylene chloride, diethyl ether was added to effect precipitation and the precipitate was collected by filtration to give 3-(benzyloxycarbonyl)-7-(R,S)-[2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-8-oxo-1,5 -diazabicyclo[3.3.0]octa-2-ene-2-carboxylic acid: n.m.r. (90 MHz, DMSO-d6): δ 2.60-4.14 (m, 5), 3.76 (s, 3), 4.64-5.20 (m, 2), 5.04 (s, 2), 7.12 (br. s, 2), 7.24 (br. s, 5), 9.01 (br. d, 1, J=7); i.r. (KBr): 3417, 1696, 1662, 1617, 1521, 1442, 1396, 1380, 1331, 1272 cm-1 ; u.v. (EtOH); λmax =231 (ε=15547), 329 (ε=11296); m.p. d>160° C.°, f.a.b.m.s. (m/e) M+1=501.

Provenance & Evidence