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

(S)-isoserine 15a (21 g, 0.20 mol) na faʻamavaeina i le tetrahydrofuran (100 mL) Ma o se solvent fefiloi o le 10percent aqueous sodium hydroxide solution (100 mL), Di-tert-butyl dicarbonate (50 mL, 0.22 mol) sa. faʻaopoopo le pa'ū.O le tali na faia i le vevela o le potu mo itula 9. O le vaega vai na faʻafetaui i le pH 2 ma le 4 mol / L hydrochloric acid, ma faʻaaogaina ma le dichloromethane / methanol (v / v = 5/1, 50 mL × 3 ) ma faʻagogo i luga o le sodium sulfate anhydrous.Fili e ala i le suction, faʻaoga i lalo o le faʻaitiitia o le mamafa, O le igoa faʻapipiʻi 15b na maua mai o se suauu e leai ni lanu (35 g, fua: 85percent).
I se vaifofo faʻafefe o S-isoserine (4.0 g, 0.038 mol) i le dioxane: H2O (100 mL, 1: 1 v / v) i le 0 ° C na faʻaopoopoina N-methylmorpholine (4.77 mL, 0.043 mol), sosoo ai ma BoC2O (11.28 mL, 0.049 mol) ma o le tali na faʻafefe i le po ma faʻamafanafana malie i le vevela potu.Glycine (1.0 g, 0.013 mol) ona faʻaopopo lea ma faʻaoso le tali mo le 20 min.O le tali na faamalūlū i le O0C ma nofo aq.NaHCO3 (75 mL) na faʻaopoopoina.Na fufulu le vaega vai i le ethyl acetate (2 x 60 mL) ona fa'asalaina lea i le pH 1 ma le NaHSO4.O lenei vaifofo na maua mai i le ethyl acetate (3 x 70 mL) ma o nei mea faʻapipiʻi tuʻufaʻatasia sa faʻamago i luga ole Na2SO4, faʻamama ma faʻamago ina ia maua ai le N-Boc-3-ammo-2(S) -hydroxy-propanoic acid e manaʻomia. (6.30 g, 0.031 mmol, 81.5 pasene fua): 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 ;I se vaifofo faʻaosofia o le S-isoserine (4.0 g, 0.038 mol) i le dioxane: H2O (100 mL, 1: 1 v / v) i le 0 ° C na faʻaopoopoina N-methylmorpholine (4.77 mL, 0.043 mol), sosoo ai ma BoC2O (11.28 mL, 0.049 mol) ma o le tali na faʻafefe i le po ma faʻamafanafana malie i le vevela potu.Glycine (1.0 g, 0.013 mol) ona faʻaopopo lea ma faʻaoso le tali mo le 20 min.O le tali na fa'alili i le 0°C ma nofo aq.NaHCO3 (75 mL) na faʻaopoopoina.Na fufulu le vaega vai i le ethyl acetate (2 x 60 mL) ona fa'asalaina lea i le pH 1 ma le NaHSO4.O le vaifofo lea na maua mai i le ethyl acetate (3 x 70 mL) ma fa'amamago nei fa'ameamea tu'ufa'atasi i luga o le Na2SO4, fa'amama ma fa'amago ina ia maua ai le N-Boc-3-amino-2(5)-hydroxy-propanoic acid e mana'omia. (6.30 g, 0.031 mmol, 81.5 pasene fua): 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.