Water → HCID 54377278, compound

Participants

Reaction Steps

A solution of [3-methoxy-4-(3-o-tolylureido)phenyl]-acetic acid (2.50 g, Reference Example 5) and sareosine ethyl ester hydrochloride(1.23 g) in dimethylformamide (75 ml) was treated with [O-(7-azabenzotriazol-1-yl)-1,1,3,3,-tetramethyluronium hexafluorophosphate] (3.03 g) and diisopropylethylamine (430 ml). The reaction mixture was stirred at room temperature for 2 hours, then treated with water (200 ml) and then filtered. The white solid was suspended in tetrahydrofuran (100 ml) and the mixture was then treated with lithium hydroxide hydrate (0.45 g) in water (20 ml). After stirring for 45 minutes the mixture was concentrated to remove the tetrahydrofuran. The remaining aqueous phase was washed with ethyl acetate then acidified by addition of hydrochloric acid (1M), then extracted three times with ethyl acetate. The combined organic extracts were washed with brine, then dried over magnesium sulphate and then evaporated to yield the title compound (2.24 g) as a white solid, m. p. 125-130° C. (with decomposition). HPLC: RT=10.83 minutes (gradient elution using a mixture of acetonitrile and water 1:4 to 4:1 v/v). MS(-ve) [M−1]−384.

Provenance & Evidence