Sodium Hydroxide → HCID 44413446, compound

Participants

Reaction Steps

A solution of methyl trans-N-tert-butyloxycarbonyl-2-(4-(5-(4-cyclopentylphenyl)-1,2,4-oxadiazol-3-yl)phenyl)-4-pyrrolidineacetate (4.4 mg, 8.3 μmol) in 2.5 mL of 20% TFA in CH2Cl2 was stirred at rt for 1 hr and then concentrated. The residue was redissolved in 5.0 mL of EtOH and sodium hydroxide (189 μL, 5.0 N, 0.95 mmol) was added. After stirring at rt for 1 hr, the reaction mixture was concentrated and the residue was purified on HPLC to give 3.5 mg (100%) of the title compound: 1H NMR (CD3OD) δ 1.60 (m, 214), 1.69 (m, 2H), 1.81 (m, 2H), 2.06 (m, 2H), 2.26 (m, 1H), 2.46 (m, 1H), 2.58 (m, 2H), 2.96 (m, 1H), 3.07 (m, 1H), 3.12 (dd, J=7.7, 11.9, 1H), 3.70 (dd, J=7.7, 11.8, 1H), 4.84 (t, J=8.6, 1H), 7.44 (d, J=8.2, 2H), 7.60 (d, J=8.4, 2H), 8.06 (d, J=8.4, 2H), 8.18 (d, J=8.2, 2H).

Provenance & Evidence