Lithium Hydroxide → HCID 131719311, compound

Participants

Reaction Steps

By the same procedure used to prepare the title compound of Example 1C, PhCH2NHCOValAlaOCH3 (671 mg, 2.00 mmole) and LiOH.OH (168 mg, 4.00 mmole) in 10% aqueous CH3OH (20 mL) gave after quenching with sulfonic acid ion exchange resin (18.0 g, 40 meq) 658 mg (100%) of pure product as an off-white flaky solid. Recyrstallization of a portion from ethyl acetate/CH3OH gave an analytical sample as very fine white crystals: mp 205°-206° C.; 1H NMR (DMSO-d6) δ 0.79 (d, J=6.8 Hz, 3H), 0.86 (d, J=6.7 Hz, 3H), 1.25 (d, J=7.3 Hz, 3H), 1.85-2.0 (m, 1H), 4.05-4.3 (m, 4H), 6.09 (d, J=9.3 Hz, 1H), 6.54 (t, J=6.0 Hz, 1H), 7.15-7.35 (m, 5H), 824 (d, J=7.0 Hz, 1H); MS (LSIMS) m/e 344 (22, M+ +Na), 322 (83, M+ +1), 233 (70), 205 (18), 189 (100); [α]D20 +15.3° (c=1.0, DMF); Analysis calculated for C16H23N3O4 : C, 59.79; H, 7.21; N, 13.08; found: C, 59.87; H, 7.30; N, 12.80.

Provenance & Evidence