1-Chloroethyl chloroformate → HCID 18782720, compound

Participants

Reaction Conditions

Reaction Steps

1-Chloroethyl chloroformate (1.9 ml, 17.6 mmol) was added dropwise at 4° C. to a solution of 7-benzyl-3-(2-methoxy-5-(5-trifluoromethyl-1H-tetrazol-1-yl)phenyl)-1-oxa-7-azaspiro[4,5]dec-3-ene (free base of Ex. 2; 6.16 g, 13.07 mmol) in dichloromethane (60 ml). The reaction mixture was stirred at -4° C. for 30 minutes, allowed to warm to room temperature over 30 minutes and stirred at room temperature for 15 minutes. The reaction mixture was concentrated in vacuo, the residual red oil dissolved in methanol (60 ml) and heated at reflux for 40 minutes. The mixture was allowed to cool, concentrated in vacuo and the residue triturated with ether to give a title compound in two crops (3.54 g, 65%), m.p. 203°-205° C.; (Found: C, 48.33; H, 4.44; N, 16.31. C17H19ClF3N5O2. 0.25H2O requires C, 48.35; H, 4.65; N, 16.58%); δH (360MHz, DMSO-d6) 1.72-1.96 (4H, m), 2.85 (1H, m), 3.11 (3H, m), 4.00 (3H, s, ArOCH3), 4.99 (2H, m, 2-CH2, 6.64 (1H, br s, 4-CH=), 7.38 (1H, d, J 8.9Hz, 3'-H), 7.65 (1H, d, J 2.5Hz, 6'-H), 7.76 (1H, dd, J 8.9, 2.5Hz, 4'-H); m/z (ES+) 382 ([M+H]+).

Provenance & Evidence