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

(S) -isoserine 15a (21 g, 0.20 mol) yachithwa kwi-tetrahydrofuran (100 mL) kunye ne-solvent edibeneyo ye-10percent yesisombululo se-sodium hydroxide (100 mL), i-Di-tert-butyl dicarbonate (50 mL, 0.22 mol) i-dropwise.Impendulo yenziwa kwindawo yokushisa kweeyure ze-9. Isigaba samanzi salungiswa kwi-pH 2 kunye ne-4 mol / L i-hydrochloric acid, kwaye ikhutshwe nge-dichloromethane / methanol (v / v = 5/1, 50 mL × 3). ) kwaye yomiswe phezu kwe-anhydrous sodium sulfate.Ihluzo ngokufunxa, gxininisa phantsi koxinzelelo oluncitshisiweyo, I-compound yesihloko 15b yafunyanwa njengeoli engenambala (35 g, isivuno: 85percent).
Kwisisombululo esichukumisayo se-S-isoserine (4.0 g, 0.038 mol) kwi-dioxane: i-H2O (100 mL, 1: 1 v / v) kwi-0 ° C yongezwa i-N-methylmorpholine (4.77 mL, 0.043 mol), ilandelwa yi-BoC2O (11.28 mL, 0.049 mol) kwaye ukusabela kwavuselelwa ngobusuku ngokufudumeza ngokuthe ngcembe kwiqondo lobushushu begumbi.I-Glycine (i-1.0 g, i-0.013 mol) yongezwa emva koko kwaye impendulo yavuselelwa i-20 min.I-reaction yapholiswa kwi-O0C kwaye yahlala i-aq.I-NaHCO3 (75 mL) yongezwa.Uluhlu olunamanzi luhlanjwe nge-ethyl acetate (2 x 60 mL) kwaye emva koko i-acidified pH 1 kunye ne-NaHSO4.Esi sisombululo saye sakhutshwa nge-ethyl acetate (3 x 70 mL) kwaye ezi zingqimba zendalo ezidityanisiweyo zomiswa phezu kwe-Na2SO4, zahluzwa kwaye zagxininiswa komile ukunika i-N-Boc-3-ammo-2 (S) efunekayo -hydroxy-propanoic acid. (6.30 g, 0.031 mmol, 81.5 ekhulwini 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) -i-hydroxy-propionic acid;Kwisisombululo esishukumisayo se-S-isoserine (4.0 g, 0.038 mol) kwi-dioxane: i-H2O (100 mL, 1: 1 v / v) kwi-0 ° C yongezwa i-N-methylmorpholine (4.77 mL, 0.043 mol), ilandelwa yi-BoC2O (11.28 mL, 0.049 mol) kwaye ukusabela kwavuselelwa ngobusuku ngokufudumeza ngokuthe ngcembe kwiqondo lobushushu begumbi.I-Glycine (i-1.0 g, i-0.013 mol) yongezwa emva koko kwaye impendulo yavuselelwa i-20 min.I-reaction yapholiswa kwi-0 ° C kwaye yahlala i-aq.I-NaHCO3 (75 mL) yongezwa.Uluhlu olunamanzi luhlanjwe nge-ethyl acetate (2 x 60 mL) kwaye emva koko i-acidified pH 1 kunye ne-NaHSO4.Esi sisombululo sakhutshwa nge-ethyl acetate (3 x 70 mL) kwaye ezi zingqimba ezidityanisiweyo ze-organic zomiswa phezu kwe-Na2SO4, zahluzwa kwaye zigxininiswe ekumiseni ukunika i-N-Boc-3-amino-2 (5) efunekayo -hydroxy-propanoic acid. (6.30 g, 0.031 mmol, 81.5 ekhulwini 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.