Lithium Hydroxide → HCID 15297596, compound

Participants

Reaction Steps

By the same procedure used to prepare AcTyr(O-t-butyl)ValAlaOH, PhCH2CH2COValAlaOCH3 (508 mg, 1.52 mmole) and LiOH.OH (319 mg, 7.6 mmole) in 10% aqueous CH3OH (15 mL) gave, after quenching with sulfonic acid ion exchange resin (17.0 g, 38 meq), 511 mg (100%) of pure product as a white powder. Recyrstallization of a portion from ethylacetate gave an analytical sample: mp 205°-206° C.; 1H NMR (DMSO-d6) δ 0.76 (d, J=6.7 Hz, 3H), 0.81 (d, J=6.8 Hz, 3H), 1.24 (d, J=7.3 Hz, 3H), 1.8-1.95 (m, 1H), 2.35-2.55 (m, 2H, partially obscured by the DMSO-d5 peak), 2.75-2.85 (m, 2H), 4.1-4.25 (m, 2H), 7.1-7.3 (m, 5H), 7.84 (d, J=9.1 Hz, 1H), 8.23 (d, J=6.5 Hz, 1H); MS (LSIMS) m/e 321 (45, M+ +1), 232 (29), 204 (11), 157 (100); [α]D20 -2.0° (c=1.0, DMF); Analysis calculated for C17H24N2O4 : C, 63.73; H, 7.55; N, 8.75; found: C, 63.78; H, 7.30; N, 8.60.

Provenance & Evidence