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

(S)-isoserine 15a (21 g, 0.20 mol) tau yaj hauv tetrahydrofuran (100 mL) Thiab ib qho hnyav ntawm 10 feem pua ​​​​aqueous sodium hydroxide tov (100 mL), Di-tert-butyl dicarbonate (50 mL, 0.22 mol) yog Ntxiv dropwise.Cov tshuaj tiv thaiv yog nqa tawm nyob rau hauv chav tsev kub rau 9 teev.The aqueous theem tau hloov mus rau pH 2 nrog 4 mol / L hydrochloric acid, thiab muab rho tawm nrog dichloromethane / methanol (v/v = 5/1, 50 mL × 3 ) thiab qhuav dhau anhydrous sodium sulfate.Lim los ntawm kev nqus, mloog zoo nyob rau hauv qhov txo qis, Lub npe compound 15b tau txais los ua cov roj tsis muaj xim (35 g, yield: 85percent).
Rau kev sib tov ntawm S-isoserine (4.0 g, 0.038 mol) hauv dioxane: H2O (100 mL, 1: 1 v / v) ntawm 0 ° C tau ntxiv N-methylmorpholine (4.77 mL, 0.043 mol), tom qab ntawd BoC2O. (11.28 mL, 0.049 mol) thiab cov tshuaj tiv thaiv tau nplawm ib hmos nrog maj mam ua kom sov rau chav sov.Glycine (1.0 g, 0.013 mol) tau ntxiv thiab cov tshuaj tiv thaiv tau nplawm rau 20 feeb.Cov tshuaj tiv thaiv tau txias rau O0C thiab zaum aq.NaHCO3 (75 mL) ntxiv.Cov txheej aqueous tau ntxuav nrog ethyl acetate (2 x 60 mL) thiab tom qab ntawd acidified rau pH 1 nrog NaHSO4.Cov tshuaj no tau muab rho tawm nrog ethyl acetate (3 x 70 mL) thiab cov txheej txheem sib xyaw ua ke no tau qhuav dhau Na2SO4, lim thiab concentrated kom qhuav kom muab qhov xav tau N-Boc-3-ammo-2(S)-hydroxy-propanoic acid. (6.30 g, 0.031 mmol, 81.5% tawm los): 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;Rau kev sib tov ntawm S-isoserine (4.0 g, 0.038 mol) hauv dioxane: H2O (100 mL, 1: 1 v / v) ntawm 0 ° C tau ntxiv N-methylmorpholine (4.77 mL, 0.043 mol), tom qab ntawd BoC2O (11.28 mL, 0.049 mol) thiab cov tshuaj tiv thaiv tau nplawm ib hmos nrog maj mam ua kom sov rau chav sov.Glycine (1.0 g, 0.013 mol) tau ntxiv thiab cov tshuaj tiv thaiv tau nplawm rau 20 feeb.Cov tshuaj tiv thaiv tau txias rau 0 ° C thiab zaum aq.NaHCO3 (75 mL) ntxiv.Cov txheej aqueous tau ntxuav nrog ethyl acetate (2 x 60 mL) thiab tom qab ntawd acidified rau pH 1 nrog NaHSO4.Cov tshuaj no tau muab rho tawm nrog ethyl acetate (3 x 70 mL) thiab cov txheej txheem sib xyaw ua ke no tau qhuav dhau Na2SO4, lim thiab concentrated kom qhuav kom muab qhov xav tau N-Boc-3-amino-2(5)-hydroxy-propanoic acid. (6.30 g, 0.031 mmol, 81.5% tawm los): 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.