Acetone → HCID 131719652, compound

Participants

Reaction Steps

In a similar manner to Example 1, t-butyl 4-[3-(4-thiocarbamoylbenzoyl)ureido]-2-(t-butoxymethoxy)phenoxyacetate (2.4 g) was reacted with iodomethane (9 ml) and acetone (130 ml) and the resultant product was treated with ammonium acetate (5 g), methanol (150 ml) and dichloromethane (150 ml) at ambient temperature. This yielded a crude solid, which was triturated with methanol, collected, washed with ether, methanol and water, and dried under high vacuum to give the title compound (1.3 g) as an off-white solid: NMR Spectrum (DMSO-d6) 1.44 (9H, s), 1.45 (9H, s), 1.77 (3H, s), 4.62 (2H, s), 4.67 (2H, s), 6.90 (1H, d), 7.09 (1H, dd), 7.29 (1H, d), 7.91 (2H, d), 8.12 (2H, d), 10.75 (1H, br s); Mass Spectrum m/Z 543 (M+H)+ ; Elemental Analysis: calculated for C27H34N4O8. 1.0 CH3CO2H. 1.25 H2O: C, 55.7%; H, 6.5%; N, 9.0%; found: C, 55.6%; H, 6.1%; N, 8.9%.

Provenance & Evidence