Acetic acid, azido-, ethyl ester → 2-(2-Azido-2-ethoxycarbonyl-vinyl)-4,5,7,8-tetrahydro-thieno[2,3-d]azepine-6-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of sodium ethoxide in ethanol (21 wt % in EtOH, 8 ml, 21.4 mmol) was diluted with additional ethanol (˜5 ml) and cooled to 0° C. To this solution was added the product from step (c) (4.50 g, 17.76 mmol) and ethyl azidoacetate (25% wt % in EtOH, 11 ml, 21.4 mmol). The reaction mixture was stirred and allowed to warm to RT over 16 hrs. The reaction mixture was then quenched by pouring into saturated aqueous NH4Cl. The aqueous mixture was extracted with Et2O (3×). The combined Et2O extracts were washed with brine, dried (MgSO4), filtered, and solvent evaporated in vacuo to give an orange oil. The crude oil was purified by flash silica-gel chromatography (gradient elution: 0 to 45% EtOAc in hexanes) to give the subtitled compound as a yellow oil (2.9 g). MS: ESI (positive): 365 (M+H).

Provenance & Evidence