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

(S) -isoserine 15a (21 g, 0.20 mol) yakanyungudutswa mutetrahydrofuran (100 mL)Uye musanganiswa wemusanganiswa we10percent aqueous sodium hydroxide solution (100 mL),Di-tert-butyl dicarbonate (50 mL, 0.22 mol) yaiva yakawedzera dropwise.Maitiro acho akaitwa pakamuri tembiricha kwemaawa 9. The aqueous phase yakagadziridzwa pH 2 ne 4 mol/L hydrochloric acid, uye yakabudiswa ne dichloromethane/methanol (v/v = 5/1, 50 mL × 3). ) uye yakaomeswa pamusoro peanhydrous sodium sulfate.Sefa nekusveta, simbisa pasi pekumanikidzwa kwakaderedzwa, Musoro wepamusoro 15b wakawanikwa semafuta asina ruvara (35 g, goho: 85percent).
Kumushonga unokurudzira weS-isoserine (4.0 g, 0.038 mol) mu dioxane: H2O (100 mL, 1: 1 v/v) pa0° C yakawedzerwa N-methylmorpholine (4.77 mL, 0.043 mol), ichiteverwa neBoC2O (11.28 mL, 0.049 mol) uye maitiro akamutswa usiku humwe nekudziya zvishoma nezvishoma kune tembiricha yekamuri.Glycine (1.0 g, 0.013 mol) yakazowedzerwa uye maitiro akamutswa kwe20 min.Kuita kwakatonhodzwa kuO0C ndokugara aq.NaHCO3 (75 mL) yakawedzerwa.Iyo aqueous layer yakagezwa ne ethyl acetate (2 x 60 mL) uye ipapo acidified kusvika pH 1 neNaHSO4.Mushonga uyu wakabva watorwa ne ethyl acetate (3 x 70 mL) uye aya akasanganiswa organic layer akaomeswa pamusoro peNa2SO4, akasefa uye akaiswa pakuoma kuti ape yaidiwa N-Boc-3-ammo-2(S) -hydroxy- propanoic acid. (6.30 g, 0.031 mmol, 81.5 muzana goho): 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 ;Kumushonga unokurudzira weS-isoserine (4.0 g, 0.038 mol) mu dioxane: H2O (100 mL, 1: 1 v/v) pa0 ° C yakawedzerwa N-methylmorpholine (4.77 mL, 0.043 mol), ichiteverwa neBoC2O (11.28 mL, 0.049 mol) uye maitiro akamutswa usiku humwe nekudziya zvishoma nezvishoma kune tembiricha yekamuri.Glycine (1.0 g, 0.013 mol) yakazowedzerwa uye maitiro akamutswa kwe20 min.Mhedzisiro yacho yakatonhodzwa kusvika ku0 ° C uye yakagara aq.NaHCO3 (75 mL) yakawedzerwa.Iyo aqueous layer yakagezwa ne ethyl acetate (2 x 60 mL) uye ipapo acidified kusvika pH 1 neNaHSO4.Mushonga uyu wakabva watorwa ne ethyl acetate (3 x 70 mL) uye aya akasanganiswa organic layer akaomeswa pamusoro peNa2SO4, akasefa uye akaiswa pakuoma kuti ape yaidiwa N-Boc-3-amino-2 (5) -hydroxy- propanoic acid. (6.30 g, 0.031 mmol, 81.5 muzana goho): 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.