Nitrogen → HCID 9939995, compound

Participants

Reaction Steps

A slurry of 1-[2-carboxy-2-propen-1-yl]-4-[[(6R)-trans-2-(diphenylmethyl carboxy)-8-oxo-7-[(2,5-dichlorophenylthio)acetamido]-5-thia-1-azabicyclo[4.2.0]-oct-2-en-3-yl]methylthio]pyridinium bromide (580 mg, 0.665 mmol) in 22 mL of CH2Cl2 was cooled to 0° C. (ice bath) under an atomosphere of N2. Anisole (2.8 mL) was added followed by trifluoroacetic acid (8 mL). The cooling bath was removed, and the reaction was allowed to stir at rt for 1 h. The solution was concentrated in vacuo to remove the CH2Cl2 and most of the trifluoroacetic acid. The residue was treated with ether to precipitate a yellow solid. This solid was collected by filtration washing with ether. The solid was stirred with ethyl acetate for 30 min. stirred with acetone for 30 min., collected by filtration, and dried in vacuo to give 322 mg (66%) of 1-[2-carboxy-2-propen-1-yl]-4-[[(6R)-trans-2-carboxy-8-oxo-7-[(2,5-dichlorophenylthio)acetamido]-5-thia-1-azabicyclo[4.2.0]-oct-2-en-3-yl]methylthio]pyridinium bromide as a tan solid. 1H NMR (DMSO-d6) δ9.27 (d, J=8 Hz, 1H), 8.73 (d, J=6 Hz, 2H), 8.06 (d, J=6 Hz, 2H), 7.45-8.48 (m, 2H), 7.24 (dd, J=2,9 Hz, 2H), 6.41 (s, 1H), 6.08 (s, 1H), 5.63 (dd, J=5,8 Hz, 1H), 5.19 (s, 2H), 5.09 (d, J=5 Hz, 1H), 4.43 (s, 2H), 3.92 (s, 2H), 3.70 (d, J=18 Hz, 1H), 3.48 (d, J=18 Hz, 1H). IR (KBr) 1774, 1702, 1680, 1628, 1106 cm-1 ; MS (ESI) 626 (MH)+, Anal: Calcd for C25H21N3O6S3Cl2 ×HBr×0.5Me2CO; C, 42.44; H, 3.13; N, 5.94. Found: C, 43.25; H, 3.42, N, 5.71.

Provenance & Evidence