52558-24-4 (S)-3-(tert-Butyloxycarbonylamino)-2-hydroxypropionic acid

(S)-isoserine 15a (21 g, 0.20 mol) ayaa lagu milmay tetrahydrofuran (100 mL) Dareen-celinta ayaa lagu sameeyay heerkulka qolka 9 saacadood. Marxaladda aqueous waxaa lagu hagaajiyay pH 2 oo leh 4 mol / L hydrochloric acid, waxaana laga soo saaray dichloromethane / methanol (v / v = 5/1, 50 mL × 3). ) oo lagu qalajiyey sodium sulfate anhydrous ah. Sifee nuugista, xoogga saar cadaadiska hoos u dhaca, Xarunta cinwaanka 15b waxaa lagu helay saliid aan midab lahayn (35 g, dhalidda: 85%).
Xalka walaaqaya ee S-isoserine (4.0 g, 0.038 mol) ee dioxane: H2O (100 mL, 1: 1 v / v) at 0 ° C ayaa lagu daray N-methylmorpholine (4.77 mL, 0.043 mol), oo ay ku xigto BoC2O (11.28 mL, 0.049 mol) falcelinta ayaa la kiciyay habeenkii iyadoo si tartiib tartiib ah loo kululeeyay heerkulka qolka.Glycine (1.0 g, 0.013 mol) ayaa markaa lagu daray oo falcelinta ayaa la walaaqay 20 min.Falcelinta waxaa lagu qaboojiyey O0C oo fadhiistay aq.NaHCO3 (75 ml) ayaa lagu daray.Lakabka aqueous waxaa lagu maydhay ethyl acetate (2 x 60 mL) ka dibna lagu daray pH 1 oo leh NaHSO4.Xalkan ayaa markaa laga soo saaray ethyl acetate (3 x 70 mL) iyo lakabyadan dabiiciga ah ee isku dhafan ayaa lagu qallajiyey Na2SO4, la sifeeyay oo xoogga saaray qallayl si loo siiyo N-Boc-3-ammo-2 (S) -hydroxy-propaanoic acid (6.30 g, 0.031 mmol, 81.5 boqolkiiba dhalid): 1H NMR (400 MHz, CDC13) δ 7.45 (bs, 1 H), 5.28 (bs, 1 H), 4.26 (m, 1 H), 3.40-3.62 (m , 2 H), 2.09 (s, 1 H), 1.42 (s, 9 H);13C NMR (IOO MHz, CDC13) δ 174.72, 158.17, 82, 71.85, 44.28, 28.45.
N-Boc-3-amino-2 (S) -hydroxy-propionic acid;Xalka walaaqaya ee S-isoserine (4.0 g, 0.038 mol) ee dioxane: H2O (100 mL, 1: 1 v / v) at 0 ° C ayaa lagu daray N-methylmorpholine (4.77 mL, 0.043 mol), oo ay ku xigto BoC2O (11.28 mL, 0.049 mol) falcelinta ayaa la kiciyay habeenkii iyadoo si tartiib tartiib ah loo kululeeyay heerkulka qolka.Glycine (1.0 g, 0.013 mol) ayaa markaa lagu daray oo falcelinta ayaa la walaaqay 20 min.Falcelinta ayaa la qaboojiyey ilaa 0°C waxaana la fadhiistay aq.NaHCO3 (75 ml) ayaa lagu daray.Lakabka aqueous waxaa lagu maydhay ethyl acetate (2 x 60 mL) ka dibna lagu daray pH 1 oo leh NaHSO4.Xalkan ayaa markaa laga soo saaray ethyl acetate (3 x 70 mL) iyo lakabyadan dabiiciga ah ee la isku daray ayaa lagu qallajiyey Na2SO4, la sifeeyay oo xoogga saaray qallayl si loo siiyo N-Boc-3-amino-2 (5) -hydroxy-propanoic acid (6.30 g, 0.031 mmol, 81.5 boqolkiiba dhalid): 1H NMR (400 MHz, CDC13) δ 7.45 (bs, 1 H), 5.28 (bs, 1 H), 4.26 (m, 1 H), 3.40-3.62 (m , 2 H), 2.09 (s, 1 H), 1.42 (s, 9 H);13C NMR (100 MHz, CDC13) δ 174.72, 158.17, 82, 71.85, 44.28, 28.45.