Anisole → HCID 13476964, compound

Participants

Reaction Steps

A solution of 50 mg of 3-(2-acetamidoethylthio)-6-(1-hydroxyethyl)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid diphenylmethyl ester and 25 μL of anisole in 1.5 mL of trifluoroacetic acid was stirred at room temperature for 10 min. The reaction mixture was evaporated to dryness, and trituration of the residue with ether afforded 30 mg (95%) of 3-(2-acetamidoethylthio)-6-(1-hydroxyethyl)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid as colorless, hydroscopic crystals. IR (Nujol mull) 1550, 1660, 1775 cm-1 ; NMR (400 MHz; acetone-d6): δ 1.24 (3H, d, J=6.5), 1.94 (3H, s), 2.98 (1H, m), 3.03 (2H, t, J=7), 3.14 (1H, ddd, J=18, 3.4, 1.2), 3.22 (1H, ddd, J=5.6, 3.9, 3.2), 3.35 (1H, dd, J=8.5, 1.7), 3.40 (2H, t, J=7), 4.05 (1H, qd, J=6.3, 4.9), 4.31 (1H, m), and 7.67 (1H, m).

Provenance & Evidence