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Glycine → ([1-(4-Acetylamino-phenoxy)-4-hydroxy-isoquinoline-3-carbonyl]-amino)-acetic acid

HRID 1866382
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1866382
C(O[C:6]([C:8]1[N:9]=[C:10]([O:22][C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:32])[CH3:31])=[CH:25][CH:24]=2)[C:11]2[C:16]([C:17]=1[O:18]C(=O)C)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])CCC.[NH2:33][CH2:34][C:35]([OH:37])=[O:36].C[O-].[Na+].CO>>[C:30]([NH:29][C:26]1[CH:25]=[CH:24][C:23]([O:22][C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]([OH:18])=[C:8]([C:6]([NH:33][CH2:34][C:35]([OH:37])=[O:36])=[O:7])[N:9]=2)=[CH:28][CH:27]=1)(=[O:32])[CH3:31]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 750GlycineHCID 887MethanolHCID 10942334Sodium MethoxideHCID 667129554-Acetoxy-1-(4-acetylamino-phenoxy)-isoquinoline-3-carboxylic acid butyl ester

Produkt 1

HCID 11200275([1-(4-Acetylamino-phenoxy)-4-hydroxy-isoquinoline-3-carbonyl]-amino)-acetic acidAusbeute 64 %

Versuchsvorschrift

A mixture of 4-Acetoxy-1-(4-acetylamino-phenoxy)-isoquinoline-3-carboxylic acid butyl ester (150 mg, 0.34 mmol), glycine (290 mg, 3.4 mmol), and 7.8 ml of a 0.5 N solution of sodium methoxide in methanol (3.9 mmol) was refluxed over the weekend with stirring. Then the solvent was evaporated in vacuo and the residue dissolved in 25 ml of water. The pH of the solution was subsequently adjusted to about 2 and the resulting slurry was extracted with ethyl acetate (3×30 ml). The combined extracts were dried over MgSO4 and evaporated in vacuo. Recrystallization of the residue from methanol/CH2Cl2 gave 86 mg of the title compound; MS-(+)-ion: M+1=396.15.

Aufarbeitung

  1. temperaturewas refluxed over the weekend
  2. customThen the solvent was evaporated in vacuo
  3. dissolutionthe residue dissolved in 25 ml of water
  4. extractionthe resulting slurry was extracted with ethyl acetate (3×30 ml)
  5. dry with materialThe combined extracts were dried over MgSO4
  6. customevaporated in vacuo
  7. customRecrystallization of the residue from methanol/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-07b851820e5142d08f20bf612b59af38
Quelldatensatz
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07629357B2

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