O[C@H:2]([C:16]1[S:17][CH:18]=[C:19]([CH3:21])[N:20]=1)[C@@H:3]([NH:5][C:6](=[O:15])[O:7]CC1C=CC=CC=1)[CH3:4].Cl>[OH-].[K+].CO.C1COCC1>[CH3:4][C@H:3]1[C@@H:2]([C:16]2[S:17][CH:18]=[C:19]([CH3:21])[N:20]=2)[O:7][C:6](=[O:15])[NH:5]1A solution of benzyl [(1S,2S)-2-hydroxy-1-methyl-2-(4-methyl-1,3-thiazol-2-yl)ethyl]carbamate (53.4 mg, 0.174 mmol) in 7.5 N aqueous KOH (1 mL), MeOH, (2 mL) and THF (4 mL) was stirred at room temperature overnight. The reaction mixture was acidified with 3N HCl and extracted with EtOAc (3×20 mL). The combined extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo to afford the product. LCMS calc.=199.1; found=199.1 (M+1)+. 1H NMR (500 MHz, CDCl3) δ 6.92 (s, 1H), 6.82 (s, 1H), 5.91 (d, J=8.2 Hz, 1H), 4.39-4.35 (m, 1H), 2.44 (s, 3H), 0.95 (d, J=6.4 Hz, 3H).
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