Lithium Hydroxide → (s)-2-Acetamido-3-(prop-2-ynyloxy)propanoic acid

Participants

Reaction Steps

Using (S)-methyl 2-acetamido-3-(prop-2-ynyloxy)propanoate (1.00 g, 5.03 mmol) and LiOH (aqueous 0.6 M sol., 8.4 mL, 5.03 mmol), and the preceding procedure gave 0.86 g (93%) of desired product as a yellow oil: Rf=0.35 (15/5/1 EtOAc/hexanes/AcOH); IR (nujol mull) 3270, 2924, 2120, 1729, 1641, 1547, 1459 cm−1; 1H NMR (DMSO-d6) δ 1.87 (s, CH3C(O)), 3.48 (t, J=2.4 Hz, CH2CCH), 3.62 (dd, J=4.1, 9.6 Hz, CHH′OCH2), 3.74 (dd, J=2.4, 9.6 Hz, CHH′OCH2), 4.16 (d, J=2.4 Hz, OCH2C), 4.41-4.47 (m, CH), 8.21-8.23 (d, J=8.4 Hz, NHCH); 13C NMR (DMSO-d6) δ 22.4 (CH3C(O)), 52.1 (CH), 57.8 (CH2CCH), 69.2 (CH2OCH2), 77.6 (CH2CCH), 79.9 (CH2CCH), 169.6, 171.5 (2 C(O)); HRMS (ESI) 186.0760 [M+H+] (calcd. for C8H12NO4 186.0766); Anal. (C8H11NO4, 0.25H2O) Calcd.: C, 50.66%; H, 6.11%; N, 7.38%. Found: C, 50.76%; H, 6.29%; N, 7.10%.

Provenance & Evidence