3339-73-9 3-Phthalimidopropionic acid

1.1;2.1 1. Synthesis yephthalic anhydride alanine: Wedzera 100g (1.12mol) yealanine kune 1000mL ine mitsipa mitatu-mitsipa flask, 170g (1.15mol) yephthalic anhydride, 5g ye triethylamine uye 650mL yakaparadzaniswa yemvura yakaitwa refluluenex. panguva yekupindura, maitiro akaitwa kusvikira pasina madonhwe emvura, tembiricha yakaderedzwa kusvika 20 ° C, tembiricha yakachengetwa kwemaawa maviri, suction filtration, sefa keke kubika Dry 240.2 g yephthalic anhydride alanine, HPLC kuchena 99.1%, goho 97.7%.
I-16.1 Synthesis ye 3-(l,3-dioxo-2,3-dihydro-lH-isoindol-2-yl)propanoic acid Mu 3-L 4-ine mitsipa yakatenderera-pasi flask inocheneswa uye inochengetwa neinert atmosphere. nitrogen, yakaiswa mhinduro ye3-aminopropanoic acid (20 g, 224.48 mmol, 1.00 equiv) uye 1,3- dihydro-2-benzofuran-l, 3-dione (33.28 g, 224.69 mmol, 1.00 equiv) muacetic acid (1,200 mL).Izvi zvakateverwa nekuwedzera kwe potassium acetate (66.0 g, 672.49 mmol, 3.00 equiv) mumabheji akati wandei pa0 ° C.Mushonga unoguma wakakurudzirwa kwe3 h pa80 ° C mubhati remafuta.Musanganiswa unoguma wakaiswa pasi pevacuum.Mhedzisiro yacho yakabva yadzimwa nekuwedzera kwe150 mL yemvura.Iyo yakaoma yakaunganidzwa nekusefa.Izvi zvakakonzera 40 g (81%) ye 3- (l ,3-dioxo-2,3- dihydro-lH-isoindol-2-yl) propanoic acid semuchena wakasimba.R/.0.15 (mu ethyl acetate: petroleum ether = 1: 1)
Musanganiswa we β-alanine (5.0 g, 0.056 mol), phthalic anhydride (8.7 g, 0.059 mol), uye DMF (20 mL) yakagadziriswa pasi pekukurudzira kwe3 h.Musanganiswa wakabuda wakatonhodzwa kusvika kukamuri tembiricha, wodirwa mumvura yechando (~ 100 mL), uye wozopepetwa nekusveta.Keke resefa rakagezwa sequentially nemvura (15 mL × 3), doro (3 mL × 3), uye ether (10 mL × 2), rozoomeswa muvacuo kupa 2e (9.9 g, 80%) semuchena. yakasimba.
137.6 Danho 6: Musanganiswa we isobenzofuran-l, 3-dione (20 g, 135 mmol) uye 3-aminopropanoic acid (12 g, 135 mmol) yakamutswa pa170 ° C kwe6h.Ona Mufananidzo 2. Pakupera kwekuita, musanganiswa wakasvibiswa nemvura uye wakabudiswa neDCM (100 mL x 3).Iyo yakasanganiswa organic layers yakaomeswa pamusoro peanhydrous sodium sulfate, yakasefa, uye yakanyudzwa pasi pekumanikidzwa kwakaderedzwa kupa 3-(l,3-dioxoisoindolin-2-yl) propanoic acid 137g (20 g, 69%) sechinhu chichena chakasimba.
3-Phthalimidopropanoic acid (4) Musanganiswa wephthalic anhydride (0.32 g, 2.2 mmol) uye b-alanine (0.19 g, 2.2 mmol) wakapiswa muflask yakavhurika kusvika 150˚C kwe2 h.Mushure mekutonhora kusvika ku rt, H2O (5 mL) yakawedzerwa uye musanganiswa wekuita wakatorwa muCH2Cl2 (2 X 20 mL).Iyo organic layer yakaomeswa pamusoro peNa2SO4, yakasefa uye yakatsikiswa kuti ipe chena yakasimba (0.3 g) mu 62% goho;IR (KBr) 1711, 2954 cm-1;mp 140-141˚C.Chigadzirwa chacho chakashandiswa padanho rinotevera pasina kumwe kucheneswa.