3339-73-9 3-Phthalimidopropionic acid

1.1;2.1 1. Synthesis ntawm phthalic anhydride alanine: Ntxiv 100g (1.12mol) ntawm alanine mus rau 1000mL peb-caj dab, 170g (1.15mol) ntawm phthalic anhydride, 5g ntawm triethylamine thiab 650mL ntawm toluene tau sib cais, dej tau sib cais. Thaum lub sij hawm cov tshuaj tiv thaiv, cov tshuaj tiv thaiv tau nqa tawm mus txog rau thaum tsis muaj dej te, qhov kub thiab txias yog txo mus rau 20 ° C, qhov kub thiab txias yog khaws cia rau 2 teev, nqus pom, lim ncuav ci ncuav qhuav qhuav 240.2 g ntawm phthalic anhydride alanine, HPLC purity 99.1%, yield 97.7%.
I-16.1 Synthesis ntawm 3-(l,3-dioxo-2,3-dihydro-lH-isoindol-2-yl) propanoic acid Rau hauv 3-L 4-caj dab puag ncig-hauv qab lub raj mis purged thiab tswj nrog ib qho chaw inert ntawm nitrogen, tau muab tso rau hauv kev daws ntawm 3-aminopropanoic acid (20 g, 224.48 mmol, 1.00 equiv) thiab 1,3- dihydro-2-benzofuran-l, 3-dione (33.28 g, 224.69 mmol, 1.00 equiv) hauv acetic acid. (1,200 mL).Qhov no tau ua raws li qhov sib ntxiv ntawm cov poov tshuaj acetate (66.0 g, 672.49 mmol, 3.00 equiv) hauv ntau pawg ntawm 0 ° C.Lub resulting tov yog stirred rau 3 h ntawm 80 ° C nyob rau hauv ib tug roj da dej.Lub resulting sib tov yog concentrated nyob rau hauv lub tshuab nqus tsev vacuum.Tom qab ntawd cov tshuaj tiv thaiv yog quenched los ntawm qhov sib ntxiv ntawm 150 mL dej.Cov khib nyiab tau sau los ntawm kev pom.Qhov no ua rau 40 g (81%) ntawm 3-(l ,3-dioxo-2,3- dihydro-lH-isoindol-2-yl) propanoic acid ua cov khoom dawb.R/.0.15 (hauv ethyl acetate: roj av ether = 1: 1)
Kev sib xyaw ntawm β-alanine (5.0 g, 0.056 mol), phthalic anhydride (8.7 g, 0.059 mol), thiab DMF (20 mL) tau refluxed hauv qab nplawm rau 3 teev.Lub resulting sib tov yog txias rau chav tsev kub, ncuav rau hauv dej khov dej (~ 100 mL), thiab ces lim los ntawm suction.Lub ncuav mog qab zib lim tau ua ntu zus nrog dej (15 mL × 3), cawv (3 mL × 3), thiab ether (10 mL × 2), thiab tom qab ntawd qhuav hauv lub tshuab nqus tsev kom muab 2e (9.9 g, 80%) raws li cov xim dawb. khov kho.
137.6 Kauj Ruam 6: Kev sib xyaw ntawm isobenzofuran-l, 3-dione (20 g, 135 mmol) thiab 3-aminopropanoic acid (12 g, 135 mmol) tau nplawm ntawm 170 ° C rau 6h.Saib daim duab 2. Thaum cov tshuaj tiv thaiv tiav, cov khoom sib tov tau diluted nrog dej thiab muab rho tawm nrog DCM (100 mL x 3).Cov khaubncaws sab nraud povtseg ntawm cov organic sib xyaw tau qhuav dhau los ntawm anhydrous sodium sulfate, lim, thiab concentrated nyob rau hauv qhov txo qis kom muab 3-(l,3-dioxoisoindolin-2-yl) propanoic acid 137g (20 g, 69%) ua cov khoom dawb.
3-Phthalimidopropanoic acid (4) Ib qho sib xyaw ntawm phthalic anhydride (0.32 g, 2.2 mmol) thiab b-alanine (0.19 g, 2.2 mmol) tau muab tso rau hauv lub khob qhib rau 150˚C rau 2 teev.Tom qab txias rau rt, H2O (5 mL) tau ntxiv thiab cov tshuaj tiv thaiv sib xyaw tau muab rho tawm hauv CH2Cl2 (2 X 20 mL).Cov txheej txheem organic tau qhuav dhau Na2SO4, lim thiab muaj zog kom muab cov khoom dawb (0.3 g) hauv 62% tawm los;IR (KBr) 1711, 2954 cm-1;mp140-141˚C.Cov khoom siv tau siv rau hauv cov kauj ruam tom ntej yam tsis muaj kev lim dej ntxiv.