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

(S)-isoserine 15a (21 g, 0.20 mol) i rewa ki te tetrahydrofuran (100 mL)A ko te whakarewa whakauru o te 10 paiheneti wairewa konutai konutai wai (100 mL), Di-tert-butyl dicarbonate (50 mL, 0.22 mol) tāpirihia te maturuturunga iho.I mahia te tauhohenga i te pāmahana rūma mo nga haora 9. Ko te wahanga wai i whakatikahia ki te pH 2 me te 4 mol/L waikawa pūhaumāota, ka tangohia ki te dichloromethane/methanol (v/v = 5/1, 50 mL × 3 ) ka whakamaroke ki runga i te konutai konutai sulfate.Tatarihia ma te momi, whakakorikori i raro i te pehanga iti,I riro te kohinga taitara 15b hei hinu taekore (35 g, hua: 85percent).
Ki te otinga whakakorikori o te S-isoserine (4.0 g, 0.038 mol) i roto i te dioxane: H2O (100 mL, 1:1 v/v) i te 0° C i tapirihia te N-methylmorpholine (4.77 mL, 0.043 mol), ka whai ko BoC2O (11.28 mL, 0.049 mol) ka whakakorikoria te tauhohenga mo te po me te whakamahana haere ki te pāmahana rūma.Kātahi ka tāpirihia te Glycine (1.0 g, 0.013 mol) ka whakakorikoria te tauhohenga mo te 20 meneti.I whakamataohia te tauhohenga ki te O0C ka noho aq.NaHCO3 (75 mL) i tapirihia.I horoia te paparanga wai ki te ethyl acetate (2 x 60 mL) ka waikawa ki te pH 1 me te NaHSO4.Ka tangohia tenei otinga me te ethyl acetate (3 x 70 mL) ka whakamaroke enei paparanga pararopi ki runga i te Na2SO4, ka tātarihia ka whakamaroke ki te whakamaroke kia hoatu te N-Boc-3-ammo-2(S)-hydroxy-propanoic acid e hiahiatia ana. (6.30 g, 0.031 mmol, 81.5 ōrau hua): 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 ;Ki te otinga whakakorikori o S-isoserine (4.0 g, 0.038 mol) i roto i te dioxane: H2O (100 mL, 1:1 v/v) i te 0° C i tapirihia te N-methylmorpholine (4.77 mL, 0.043 mol), whai muri ko BoC2O (11.28 mL, 0.049 mol) ka whakakorikoria te tauhohenga mo te po me te whakamahana haere ki te pāmahana rūma.Kātahi ka tāpirihia te Glycine (1.0 g, 0.013 mol) ka whakakorikoria te tauhohenga mo te 20 meneti.I whakamataohia te tauhohenga ki te 0°C ka noho aq.NaHCO3 (75 mL) i tapirihia.I horoia te paparanga wai ki te ethyl acetate (2 x 60 mL) ka waikawa ki te pH 1 me te NaHSO4.Ka tangohia tenei otinga ki te ethyl acetate (3 x 70 mL) ka whakamaroke enei paparanga waro whakakotahi ki runga i te Na2SO4, ka tātarihia ka whakamaroke kia hoatu te N-Boc-3-amino-2(5)-hydroxy- propanoic acid e hiahiatia ana. (6.30 g, 0.031 mmol, 81.5 ōrau hua): 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.