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

(S) -isoserine 15a (21 g, 0.20 mol) yancibilika ku-tetrahydrofuran (100 mL)Futhi i-solvent exubile engu-10percent yesisombululo se-aqueous sodium hydroxide (100 mL),Di-tert-butyl dicarbonate (50 mL, 0.22 mol) yaba i-dropwise.Ukusabela kwenziwa ezingeni lokushisa elivamile amahora angu-9. Isigaba samanzi salungiswa ukuze sibe pH 2 nge-4 mol/L hydrochloric acid, futhi sikhishwe nge-dichloromethane/methanol (v/v = 5/1, 50 mL × 3 ) futhi omiswe phezu kwe-anhydrous sodium sulfate.Hlunga ngokumunca, gxilisa ngaphansi kwengcindezi encishisiwe,Inhlanganisela yesihloko 15b itholwe njengamafutha angenambala (35 g, isivuno: 85percent).
Kusixazululo esishukumisayo se-S-isoserine (4.0 g, 0.038 mol) ku-dioxane: i-H2O (100 mL, 1:1 v/v) ku-0° C yengezwe i-N-methylmorpholine (4.77 mL, 0.043 mol), ilandelwa yi-BoC2O (11.28 mL, 0.049 mol) futhi ukusabela kwashukunyiswa ngobusuku obubodwa ngokufudunyezwa kancane kancane kuzinga lokushisa legumbi.I-Glycine (1.0 g, 0.013 mol) yabe yengezwa futhi ukusabela kwashukunyiswa imizuzu engama-20.Ukusabela kwehliselwe ku-O0C futhi kwahlala ngokulinganayo.I-NaHCO3 (75 mL) yengeziwe.Ungqimba olunamanzi lugezwe nge-ethyl acetate (2 x 60 mL) bese lwenziwa i-asidi yaba yi-pH 1 nge-NaHSO4.Lesi sixazululo sabe sesikhishwa nge-ethyl acetate (3 x 70 mL) futhi lezi zingqimba zemvelo ezihlanganisiwe zomiswa phezu kwe-Na2SO4, zahlungwa futhi zagxiliswa ekomisweni ukuze kunikezwe i-N-Boc-3-ammo-2(S) efunekayo -hydroxy- propanoic acid. (6.30 g, 0.031 mmol, 81.5% isivuno): 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.
I-N-Boc-3-amino-2(S)-hydroxy-propionic acid ;Kusixazululo esishukumisayo se-S-isoserine (4.0 g, 0.038 mol) ku-dioxane: i-H2O (100 mL, 1:1 v/v) ku-0° C yengezwe i-N-methylmorpholine (4.77 mL, 0.043 mol), ilandelwa yi-BoC2O (11.28 mL, 0.049 mol) futhi ukusabela kwashukunyiswa ngobusuku obubodwa ngokufudunyezwa kancane kancane kuzinga lokushisa legumbi.I-Glycine (1.0 g, 0.013 mol) yabe yengezwa futhi ukusabela kwashukunyiswa imizuzu engama-20.Ukusabela kupholiswe ku-0°C futhi kwahlala ngokulinganayo.I-NaHCO3 (75 mL) yengeziwe.Ungqimba olunamanzi lwagezwa nge-ethyl acetate (2 x 60 mL) lwase lwenziwa i-asidi yaba yi-pH 1 nge-NaHSO4.Lesi sixazululo sabe sesikhishwa nge-ethyl acetate (3 x 70 mL) futhi lezi zingqimba zemvelo ezihlanganisiwe zomiswa phezu kwe-Na2SO4, zahlungwa futhi zagxiliswa ekomeni ukuze kunikezwe i-N-Boc-3-amino-2(5) efunekayo -hydroxy- propanoic acid. (6.30 g, 0.031 mmol, 81.5% isivuno): 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.