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

(S) -isoserine 15a (21 g, 0.20 mol) inasungunuka mu tetrahydrofuran (100 mL) Ndipo chosungunulira chosakaniza cha 10percent amadzimadzi sodium hydroxide solution (100 mL), Di-tert-butyl dicarbonate (50 ml, 0.22 mol) chinali Anawonjezera dropwise.Zochitazo zinkachitika kutentha kwa firiji kwa maola 9. Gawo lamadzimadzi linasinthidwa kukhala pH 2 ndi 4 mol / L hydrochloric acid, ndi yotengedwa ndi dichloromethane/methanol (v/v = 5/1, 50 mL × 3). ) ndi zouma pa anhydrous sodium sulfate. Sefa ndi kuyamwa, kuika maganizo pansi pa kupanikizika kwafupika, Mutu wapawiri 15b unapezedwa ngati mafuta opanda mtundu (35 g, zokolola: 85percent).
Njira yothetsera S-isoserine (4.0 g, 0.038 mol) mu dioxane: H2O (100 mL, 1: 1 v / v) pa 0 ° C inawonjezeredwa N-methylmorpholine (4.77 mL, 0.043 mol), yotsatiridwa ndi BoC2O (11.28 ml, 0.049 mol) ndipo zomwe zidachitika usiku wonse ndikuwotha pang'onopang'ono mpaka kutentha.Glycine (1.0 g, 0.013 mol) adawonjezeredwa ndipo zomwe zidachitikazo zidalimbikitsidwa kwa mphindi 20.Zomwe zidakhazikika ku O0C ndikukhala aq.NaHCO3 (75 mL) idawonjezedwa.Wosanjikiza amadzimadzi anatsukidwa ndi ethyl acetate (2 x 60 mL) kenako acidified kuti pH 1 ndi NaHSO4.Njirayi idatulutsidwa ndi ethyl acetate (3 x 70 mL) ndipo zigawo izi zophatikizana zidawumitsidwa pamwamba pa Na2SO4, zosefedwa ndikuwunikiridwa kuti ziwume kuti apatse N-Boc-3-ammo-2 (S) -hydroxy-propanoic acid yomwe akufuna. (6.30 g, 0.031 mmol, 81.5 peresenti zokolola): 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 asidi;Njira yothetsera S-isoserine (4.0 g, 0.038 mol) mu dioxane: H2O (100 mL, 1: 1 v / v) pa 0 ° C inawonjezeredwa N-methylmorpholine (4.77 mL, 0.043 mol), yotsatiridwa ndi BoC2O (11.28 ml, 0.049 mol) ndipo zomwe zidachitika usiku wonse ndikuwotha pang'onopang'ono mpaka kutentha.Glycine (1.0 g, 0.013 mol) adawonjezeredwa ndipo zomwe zidachitikazo zidalimbikitsidwa kwa mphindi 20.Zomwe zidakhazikika mpaka 0 ° C ndipo zidakhazikika.NaHCO3 (75 mL) idawonjezedwa.Wosanjikiza amadzimadzi anatsukidwa ndi ethyl acetate (2 x 60 mL) kenako acidified kuti pH 1 ndi NaHSO4.Njirayi idatulutsidwa ndi ethyl acetate (3 × 70 mL) ndipo zigawo izi zophatikizika zimawumitsidwa pa Na2SO4, zosefedwa ndikuwunikiridwa kuti ziume kuti zipereke N-Boc-3-amino-2 (5) -hydroxy-propanoic acid yomwe akufuna. (6.30 g, 0.031 mmol, 81.5 peresenti zokolola): 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.