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

(S) -isoserine 15a (21 g, 0.20 mol) e ile ea qhibiliha ka tetrahydrofuran (100 mL) 'Me motsoako o tsoakiloeng oa 10percent aqueous sodium hydroxide solution (100 ml), Di-tert-butyl dicarbonate (50 ml, 0.22 mol) e ne e le mol. e ekelitsoe dropwise.Karabelo e ile ea etsoa ka mocheso oa kamore bakeng sa lihora tse 9. Karolo ea metsi e ile ea fetoloa ho pH 2 le 4 mol / L hydrochloric acid, 'me ea ntšoa ka dichloromethane/methanol (v/v = 5/1, 50 mL × 3). ) 'me o omisitsoe holim'a anhydrous sodium sulfate.Sefa ka ho monya, tsepamisa maikutlo tlas'a khatello e fokotsehileng,Motsoako oa sehlooho 15b o ile oa fumanoa e le oli e se nang mebala (35 g, chai: 85percent).
Ho tharollo e susumetsang ea S-isoserine (4.0 g, 0.038 mol) ka dioxane: H2O (100 mL, 1: 1 v / v) ka 0 ° C e kenyelelitsoe N-methylmorpholine (4.77 mL, 0.043 mol), e lateloa ke BoC2O (11.28 mL, 0.049 mol) mme karabelo e ile ea tsosoa bosiu bo le bong ka ho futhumala butle-butle ho mocheso oa kamore.Glycine (1.0 g, 0.013 mol) e ile ea eketsoa mme karabelo e ile ea tsosoa ka metsotso e 20.Karabelo e ile ea pholile ho O0C mme ea lula hantle.NaHCO3 (75 mL) e kentsoe.Lera le nang le metsi le ile la hlatsuoa ka ethyl acetate (2 x 60 mL) 'me la e-ba acidified ho pH 1 le NaHSO4.Tharollo ena e ile ea ntšoa ka ethyl acetate (3 x 70 mL) 'me likarolo tsena tse kopantsoeng tsa manyolo li ile tsa omisoa holim'a Na2SO4, tsa tlhotloa le ho tsepamisa mohopolo ho omella ho fana ka N-Boc-3-ammo-2 (S) -hydroxy- propanoic acid e lakatsehang. (6.30 g, 0.031 mmol, 81.5 peresente): 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 ;Ho tharollo e susumetsang ea S-isoserine (4.0 g, 0.038 mol) ka dioxane: H2O (100 mL, 1: 1 v / v) ka 0 ° C e ile ea eketsoa N-methylmorpholine (4.77 mL, 0.043 mol), e lateloa ke BoC2O (11.28 mL, 0.049 mol) mme karabelo e ile ea tsosoa bosiu bo le bong ka ho futhumala butle-butle ho mocheso oa kamore.Glycine (1.0 g, 0.013 mol) e ile ea eketsoa mme karabelo e ile ea tsosoa ka metsotso e 20.Karabelo e ile ea pholile ho 0 ° C 'me ea lula hantle.NaHCO3 (75 mL) e kentsoe.Lera le nang le metsi le ile la hlatsuoa ka ethyl acetate (2 x 60 mL) 'me la e-ba acidified ho pH 1 le NaHSO4.Tharollo ena e ile ea ntšoa ka ethyl acetate (3 x 70 mL) 'me likarolo tsena tse kopantsoeng tsa manyolo li ile tsa omisoa holim'a Na2SO4, tsa hloekisoa le ho tsepamisa mohopolo ho omella ho fana ka N-Boc-3-amino-2 (5) -hydroxy-propanoic acid e lakatsehang. (6.30 g, 0.031 mmol, 81.5 peresente): 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.