Hydrochloric Acid → HCID 20737797, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl 3-[5-(R)-benzyloxymethyl-1-[4-[N′-(2-methylphenyl) ureido]-3-methoxyphenylacetyl]-2-(S)-pyrrolidinylmethoxy]benzoate (185 mg, 0.28 mmol) in MeOH-THF (2:5, 7 ml) was added 1.0 M-NaOH (860 ml, 0.86 mmol) at rt, and the resulting mixture was heated at 60° C. with stirring for 1 h. The reaction mixture was poured into 1N-HCl, then extracted with CHCl3. The organic layer was washed with brine, drying over anhydrous Na2SO4, then concentrated in vacuo. The residue was chromatographed on silica gel with CHCl3-MeOH (5:1) as eluent to give129 (171 mg, 94%) as a colorless amorphous solid. MW 637.72 1H-NMR (CD3OD), mixture of rotamars δ 1.89–2.37 (series of m, 4 H), 2,29 (s, 3 H), 3.52–4.53 (series of m, 8 H), 3.66 and 3.74 (s, total 3 H), 4.85 (s, 2 H), 6.66–7.98 (series of m, 16 H); MS (ESI) m/z, 638 (M++H), 660 (M++Na+); Anal. Calcd for C37H39N3O7.H2O: C, 67.77; H, 6.30; N, 6.41. Found: C, 67.40; H, 5.95: N, 6.14.

Provenance & Evidence