Anisole → HCID 13476963, compound

Participants

Reaction Steps

A solution of 150 mg of 3-(2'-acetamidoethylthio)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid, diphenylmethyl ester, and 130 mg of anisole in 1 mL of trifluoroacetic acid was stirred at ambient temperature for 15 min. The solvent was then removed by a stream of nitrogen leaving a residue which was crystallized from ether to afford 85 mg (92%) of 3-(2'-acetamidoethylthio)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid as colorless crystals, mp 150° to 152°. IR (Nujol): 1640, 1660, 1785, 3150 cm-1 ; NMR (CDCl3 /DMSO-d6): δ 1.93 (3H, s), 2.8-3.0 (5H, m), 3.1-3.4 (4H, m), 4.43 (1H, m), and 7.43 (1H, m). HRMS: The molecular ion (m/z 269) was not observed; however, a major fragment corresponding to loss of ketene from the molecular ion was mass measured: Calcd for C10H13O3NS, 227.0615; found, 227.0616.

Provenance & Evidence