3339-73-9 3-Phthalimidopropionic acid

1.1;2.1 1. Ukwenziwa kwe-phthalic anhydride alanine: Yongeza i-100g (1.12mol) ye-alanine kwi-1000mL i-flask enentamo ezintathu, i-170g (1.15mol) ye-phthalic anhydride, i-5g ye-triethylamine kunye ne-650ml ye-reactivated ye-refluluenex eyahlukileyo kwi-reactivity yamanzi. ngexesha lokusabela, ukusabela kuqhutywe de kungabikho manzi, ubushushu behliswa ukuya kuma-20 ° C, ubushushu bagcinwa iiyure ezi-2, ukuhluzwa kwe-suction, ukubhaka ikhekhe lokucoca Dry 240.2 g ye-phthalic anhydride alanine, i-HPLC yokucoca i-99.1%, isivuno sama-97.7%.
I-16.1 I-Synthesis ye-3-(l,3-dioxo-2,3-dihydro-lH-isoindol-2-yl)propanoic acid Kwiflaski eyi-3-L enentamo ezi-4 engqukuva esezantsi ecocwe kwaye igcinwe kunye nomoya ongasebenziyo initrogen, yafakwa isisombululo se-3-aminopropanoic acid (20 g, 224.48 mmol, 1.00 equiv) kunye ne-1,3- dihydro-2-benzofuran-l, 3-dione (33.28 g, 224.69 mmol, 1.00 equiv) kwi-acetic acid (1,200 ml).Oku kulandelwe kukongezwa kwe-potassium acetate (66.0 g, 672.49 mmol, 3.00 equiv) kwiibhetshi ezininzi kwi-0 °C.Isisombululo esibangelwayo sixutywe kwi-3 h kwi-80 ° C kwindawo yokuhlamba ioli.Umxube obangelwayo wawugxininiswe phantsi kwe-vacuum.Ukusabela kwacinywa ngokongezwa kwe-150 mL yamanzi.Izinto eziqinileyo zaqokelelwa ngokuhluzwa.Oku kubangele i-40 g (81%) ye-3- (l, 3-dioxo-2,3- dihydro-lH-isoindol-2-yl) ipropanoic acid njengento eqinile emhlophe.R/.0.15 (kwi-ethyl acetate:i-ether yepetroleum = 1 : 1)
Umxube we-β-alanine (5.0 g, 0.056 mol), i-phthalic anhydride (8.7 g, 0.059 mol), kunye ne-DMF (20 mL) yaxutywa phantsi kwe-3 h.Umxube owenziweyo wapholiswa kwiqondo lobushushu begumbi, wagalelwa kumanzi omkhenkce (~100 mL), waze wahluzwa ngokufunxa.Ikeyiki yokucoca yahlanjwa ngokulandelelana ngamanzi (15 mL × 3), utywala (3 mL × 3), kunye ne-ether (10 mL × 2), yaze yomiswa kwivacuo ukunika 2e (9.9 g, 80%) njengomhlophe. eqinileyo.
137.6 Inyathelo lesi-6: Umxube we-isobenzofuran-l, 3-dione (20 g, 135 mmol) kunye ne-3-aminopropanoic acid (12 g, 135 mmol) yaxutywa kwi-170 ° C nge-6h.Jonga umzobo 2. Ekugqityweni kwempendulo, umxube uhlanjululwe ngamanzi kwaye ukhutshwe nge-DCM (100 mL x 3).Iingqimba ezidibeneyo zezinto eziphilayo zomiswa phezu kwe-anhydrous sulfate ye-sodium, yahluzwa, kwaye igxininiswe phantsi koxinzelelo oluncitshisiweyo ukunika i-3- (l, 3-dioxoisoindolin-2-yl) i-propanoic acid 137g (20 g, 69%) njengento eqinile emhlophe.
I-3-Phthalimidopropanoic acid (4) Umxube we-phthalic anhydride (0.32 g, 2.2 mmol) kunye ne-b-alanine (0.19 g, 2.2 mmol) ishushu kwi-flask evulekile ukuya kwi-150˚C kwi-2 h.Emva kokupholisa kwi-rt, i-H2O (i-5 mL) yongezwa kwaye umxube wokusabela ukhutshwe kwi-CH2Cl2 (2 X 20 mL).I-organic layer yomiswa phezu kwe-Na2SO4, yahluzwa kwaye igxininiswe ukunika i-white solid (0.3 g) kwi-62% yesivuno;IR (KBr) 1711, 2954 cm-1;mp 140-141˚C.Imveliso isetyenziswe kwisinyathelo esilandelayo ngaphandle kokucocwa ngakumbi.