Water → HCID 54026547, compound

Participants

Reaction Steps

In a 25 mL round bottomed flask a solution of ethyl-4-[(4-(1,1-dimethylethoxycarbonyl)-4,4'-bipiperidinyl-1-carbonyl)amino]-3-methylphenoxyacetate (31-4) (100 mg, 0.2 mmol), 1M LiOH, (0.6 mL, 0.6 mmol), H2O (5 mL), THF (5 mL), and MeOH (5 mL) was stirred at ambient temperature 3 h. The reaction was concentrated in vacuo, then dissolved in CHCl3 (20 mL). The CHCl3 extract was washed (1N HCl, H2O, and brine), dried (NaSO4), filtered, and concentrated to yield 4-[(4-(1,1-dimethylethoxycarbonyl)-4,4'-bipiperidinyl-1-carbonyl)amino]-3-methylphenoxyacetic acid (31-5). 1H NMR (CDCl3): δ 1.22 (br m, 6H), 1.46 (s, 9H), 1.6 (br m, 4H), 2.2 (s, 3H), 2.6 (br t, 2H), 2.79 (t, j=11 Hz, 2H), 4.0 (br m, 5H), 4.58 (s, 2H), 6.1 (dd, j=9, 2 Hz, 1H), 6.75 (d, j=2 Hz, 1H), 7.21 (d, j=9 Hz, 1H), 8.1 (s, 1H).

Provenance & Evidence