3339-73-9 3-Phthalimidopropionic acid

1.1;2.1 1. Tšimoloho ea phthalic anhydride alanine: Eketsa 100g (1.12mol) ea alanine ho 1000mL e nang le melalala e meraro, 170g (1.15mol) ea phthalic anhydride, 5g ea triethylamine le 650ml e arohaneng ea metsi ho refluluenex. nakong ea karabelo, karabelo e ile ea etsoa ho fihlela ho se marotholi a metsi, mocheso o theohetse ho 20 ° C, mocheso o ne o bolokoa lihora tse 2, ho suction filtration, ho baka kaka ea filthara Dry 240.2 g ea phthalic anhydride alanine, HPLC bohloeki 99.1%. lihlahisoa 97.7%.
I-16.1 Synthesis of 3-(l,3-dioxo-2,3-dihydro-lH-isoindol-2-yl) propanoic acid Ka har'a 3-L e 4-L, e chitja e tlase-tlase e hloekisitsoeng le ho bolokoa ka moea o sa sebetseng oa. nitrogen, e behiloe tharollo ea 3-aminopropanoic acid (20 g, 224.48 mmol, 1.00 equiv) le 1,3- dihydro-2-benzofuran-l, 3-dione (33.28 g, 224.69 mmol, 1.00 equiv) ka acetic acid (1,200 di ml).Sena se ile sa lateloa ke ho kenyelletsoa ha potassium acetate (66.0 g, 672.49 mmol, 3.00 equiv) ka lihlopha tse 'maloa ka 0 °C.Tharollo e hlahisoang e ile ea tsosoa bakeng sa 3 h ho 80 ° C ka bateng ea oli.Sephetho le motsoako ne concentrated tlas'a vacuum.Karabelo e ile ea tima ka ho eketsa 150 ml ea metsi.Lintho tse tiileng li ne li bokelloa ka ho sefa.Sena se ile sa fella ka 40 g (81%) ea 3-(l ,3-dioxo-2,3- dihydro-lH-isoindol-2-yl) propanoic acid e le 'mala o mosoeu.R/.0.15 (ka ethyl acetate: petroleum ether = 1: 1)
Motsoako oa β-alanine (5.0 g, 0.056 mol), phthalic anhydride (8.7 g, 0.059 mol), le DMF (20 mL) e ile ea ts'oaroa ha e ntse e tsosoa ka lihora tse 3.Motsoako o hlahisitsoeng o ile oa pholile ho fihlela mocheso oa kamore, o tšeloa ka metsing a leqhoa (~ 100 mL), ebe o sefuoa ka ho monya.Sesefa kuku e ile ea hlatsuoa ka tatellano ka metsi (15 mL × 3), joala (3 mL × 3), le ether (10 mL × 2), ebe e omisitsoe ka vacuo ho fana ka 2e (9.9 g, 80%) e le tšoeu. tiileng.
137.6 Mohato oa 6: Motsoako oa isobenzofuran-l, 3-dione (20 g, 135 mmol) le 3-aminopropanoic acid (12 g, 135 mmol) e ile ea tsosoa ka 170 ° C bakeng sa 6h.Sheba Setšoantšo sa 2. Ha karabelo e phethoa, motsoako o ne o hlapolotsoe ka metsi 'me o ntšoa ka DCM (100 mL x 3).Likarolo tse kopantsoeng tsa manyolo li ne li omisitsoe holim'a anhydrous sodium sulfate, e tlhotliloeng, 'me e tsepamisitsoe tlas'a khatello e fokotsehileng ho fana ka 3-(l,3-dioxoisoindolin-2-yl) propanoic acid 137g (20 g, 69%) e le tiileng e tšoeu.
3-Phthalimidopropanoic acid (4) Motsoako oa phthalic anhydride (0.32 g, 2.2 mmol) le b-alanine (0.19 g, 2.2 mmol) o futhumetse ka botlolong e bulehileng ho 150˚C bakeng sa 2 h.Kamora ho pholile ho rt, H2O (5 mL) e ile ea eketsoa mme motsoako oa karabelo o ile oa ntšoa ka CH2Cl2 (2 X 20 mL).Lera la manyolo le ne le omisitsoe ho feta Na2SO4, le tlhotliloeng le ho tsepamisa mohopolo ho fana ka 'mala o mosoeu (0.3 g) ka lihlahisoa tsa 62%;IR (KBr) 1711, 2954 cm-1;mp 140-141˚C.Sehlahisoa se ile sa sebelisoa mohatong o latelang ntle le ho hloekisoa ho eketsehileng.