Triethylamine → HCID 20162889, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (23) (418 mg) in dry dichloromethane (10 ml) containing triethylamine (222 mg) at 0° C. was treated with a solution of 2-(p-nitrobenzyloxycarbonyl)-2-thien-3-ylacetylchloride (407 mg) in dry dichloromethane (5 ml). The mixture was stirred at 0° C. for 15 minutes, then allowed to warm to room temperature. After 1 hour the mixture was washed successively with sat. NaHCO3, water, dilute HCl, water and brine. The organic phase was dried (MgSO4), filtered and evaporated. Chromatography of the residue on silica gel gave the product (39) (496 mg) as a foam. νmax(CHCl3) 3390, 1745, 1685, 1525 and 1350 cm-1 ; δppm (CDCl3) (90 MHz) 0.97 (s, 9H), 2.18 and 2.21(both s, together 3H), 3.31 and 3.73 and, 3.33 and 3.75 (both ABq, together 2H, J7 Hz), 4.79 and 4.81 (both s, together 1H), 5.31(s, 2H), 7.01 (s, 1H, exch. D2O), 7.10 to 7.60 (m, 5H), 8.22(s, 2H, J9 Hz), (--Si(CH3)2 obscured by TMS).

Provenance & Evidence