3339-73-9 3-Phthalimidopropionic acid

1.1;2.1 1. Akopọ ti phthalic anhydride alanine: Fi 100g (1.12mol) ti alanine si 1000mL ọpọn ọrùn mẹta, 170g (1.15mol) ti phthalic anhydride, 5g ti triethylamine ati 650mL ti omi ti a ya sọtọ si refluene ti ya sọtọ, lakoko iṣesi, a ṣe iṣesi naa titi ti omi ko fi silẹ, iwọn otutu ti lọ silẹ si 20 ° C, iwọn otutu ti wa ni fipamọ fun awọn wakati 2, sisẹ mimu, yan akara oyinbo ti o gbẹ 240.2 g ti phthalic anhydride alanine, mimọ HPLC 99.1%, ikore 97.7%.
I-16.1 Synthesis ti 3- (l,3-dioxo-2,3-dihydro-lH-isoindol-2-yl)propanoic acid Sinu 3-L 4-orun yika-isalẹ ọpọn ti a ti wẹ ati titọju pẹlu afẹfẹ inert ti nitrogen, ti a gbe ojutu ti 3-aminopropanoic acid (20 g, 224.48 mmol, 1.00 equiv) ati 1,3-dihydro-2-benzofuran-l,3-dione (33.28 g, 224.69 mmol, 1.00 equiv) ni acetic acid. (1,200 milimita).Eyi ni atẹle pẹlu afikun ti potasiomu acetate (66.0 g, 672.49 mmol, 3.00 equiv) ni ọpọlọpọ awọn ipele ni 0 °C.Abajade ojutu ti a ru fun 3 h ni 80 °C ni iwẹ epo.Abajade adalu ti a ogidi labẹ igbale.Idahun naa lẹhinna pa nipasẹ afikun ti 150 milimita ti omi.Awọn ipilẹ ti a gba nipasẹ sisẹ.Eyi yorisi ni 40 g (81%) ti 3- (l,3-dioxo-2,3- dihydro-lH-isoindol-2-yl)propanoic acid bi funfun ti o lagbara.R/.0.15 (ni ethyl acetate: epo ether = 1: 1)
Adalu β-alanine (5.0 g, 0.056 mol), phthalic anhydride (8.7 g, 0.059 mol), ati DMF (20 milimita) ni a tun pada labẹ gbigbọn fun awọn wakati 3.Abajade ti a ti tutu si iwọn otutu yara, ti a dà sinu omi yinyin (~ 100 milimita), ati lẹhinna ti a ti sọ di mimọ nipasẹ mimu.A ti fọ akara oyinbo naa ni atẹlera pẹlu omi (15 milimita × 3), oti (3 milimita × 3), ati ether (10 milimita × 2), ati lẹhinna gbẹ ni vacuo lati fun 2e (9.9 g, 80%) bi funfun ṣinṣin.
137.6 Igbesẹ 6: Adalu isobenzofuran-l,3-dione (20 g, 135 mmol) ati 3-aminopropanoic acid (12 g, 135 mmol) ni a mu ni 170 ° C fun 6h.Wo Nọmba 2. Lẹhin ipari ifasẹyin, a ti fo adalu naa pẹlu omi ati fa jade pẹlu DCM (100 mL x 3).Awọn fẹlẹfẹlẹ Organic ni idapo ni a gbẹ lori sulfate sodium anhydrous, filtered, ati ogidi labẹ titẹ ti o dinku lati fun 3- (l,3-dioxoisoindolin-2-yl) propanoic acid 137g (20 g, 69%) bi funfun to lagbara.
3-Phthalimidopropanoic acid (4) Adalu phthalic anhydride (0.32 g, 2.2 mmol) ati b-alanine (0.19 g, 2.2 mmol) ni a kikan ninu ọpọn ṣiṣi si 150˚C fun wakati 2.Lẹhin ti itutu agbaiye si rt, H2O (5 milimita) ti fi kun ati pe a ti yọ adalu ifasilẹ ni CH2Cl2 (2 X 20 mL).Awọn Organic Layer ti gbẹ lori Na2SO4, filtered ati ogidi lati fun a funfun ri to (0.3 g) ni 62% ikore;IR (KBr) 1711, 2954 cm-1;mp 140-141˚C.A lo ọja naa ni igbesẹ ti n tẹle laisi isọdọtun siwaju.