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Dimethyl Sulfoxide → 4-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]butanoic acid, methyl ester

HRID 1534960
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Reaktionsgleichung

Reaktionsgleichung von HRID 1534960
[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([O:15]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH:5]=[N:4][C:3]1=2.Cl.[NH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31].CS(C)=O.C(N(CC)CC)C>CC(C)=O>[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([NH:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[O:15])[CH:5]=[N:4][C:3]1=2
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Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 27563834-Aminobutyric acid methyl ester hydrochlorideHCID 1359739573-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 4-nitrophenyl ester

Produkt 1

HCID 1364033614-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]butanoic acid, methyl esterAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

0.300 g (0.9111 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 4-nitrophenyl ester (AIT-0081) and 0.142 g (0.925 mmol) of gamma amino butyric acid, methyl ester hydrochloride were placed into a 10 ml round bottom flask with a magnetic stirring bar and 2 ml dimethylsulfoxide. To this solution was added 0.100 g (0.988 mmol) of triethylamine. The solution immediately turned green and was stirred at room temperature for one hour. Then 5 ml of acetone was added and the solution was filtered. The mother liquor was treated with ether (approximately 35 ml) to precipitate the product. Upon filtration and washing with ether, 232 mg of a white solid 4-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]butanoic acid, methyl ester (AIT-0092) was obtained. Yield: 83%.

Aufarbeitung

  1. filtrationthe solution was filtered
  2. additionThe mother liquor was treated with ether (approximately 35 ml)
  3. customto precipitate the product
  4. filtrationUpon filtration
  5. washwashing with ether

Quellen und Nachweise

ORD-Eintrag
ord-cab939ba634247a2b194ab0ec3f8e44d
Quelldatensatz
uspto-grants-1992_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05091432

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