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Lithium Hydroxide → beta-[[2(R)-[[[[4(aminoiminomethyl)phenyl]amino]carbonyl]amino]methyl-propanoyl]-amino]1,3-benzodioxole-5-propanoic acid

HRID 1034268
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1034268
[NH2:1][N:2]=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH:13][CH2:14][C@@H:15]([CH3:35])[C:16]([NH:18][CH:19]([C:26]2[CH:34]=[CH:33][C:29]3[O:30][CH2:31][O:32][C:28]=3[CH:27]=2)[CH2:20][C:21]([O:23]CC)=[O:22])=[O:17])=[O:12])=[CH:6][CH:5]=1.[OH-].[Li+]>CO.O>[NH2:1][N:2]=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH:13][CH2:14][C@@H:15]([CH3:35])[C:16]([NH:18][CH:19]([C:26]2[CH:34]=[CH:33][C:29]3[O:30][CH2:31][O:32][C:28]=3[CH:27]=2)[CH2:20][C:21]([OH:23])=[O:22])=[O:17])=[O:12])=[CH:6][CH:5]=1
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Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 86747887ethyl beta-[[2(R)-[[[[4-(aminoiminomethyl)phenyl]amino]carbonyl]-amino]methylpropanoyl]amino]-1,3-benzodioxole-5-propanoate

Produkt 1

HCID 86747886beta-[[2(R)-[[[[4(aminoiminomethyl)phenyl]amino]carbonyl]amino]methyl-propanoyl]-amino]1,3-benzodioxole-5-propanoic acidAusbeute 71,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22242641Methanol--water (1/1)
Lösungsmittel

Versuchsvorschrift

A portion of ethyl β-[[2(R)-[[[[4-(aminoiminomethyl)phenyl]amino]carbonyl]amino]methylpropanoyl]amino]-1,3-benzodioxole-5-propanoate (0.18 g; 0.37 mmoles)) was then treated with 1N lithium hydroxide in methanol/water (1:1; 10 ml) for 15 min. The solvents were evaporated under reduced pressure and the residue was dissolved in water/acetonitrile. The crude product was purified by HPLC (C-18 DeltaPak column) using a gradient of acetonitrile/water/trifluoroacetic acid. Both diastereomers were separated and the desired fractions were lyophilized to give 121 mg of white solid (71% combined yield). FAB-MS: MH+ =456.3 (isomer 1) and 456.2 (isomer 2).

Aufarbeitung

  1. customThe solvents were evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in water/acetonitrile
  3. customThe crude product was purified by HPLC (C-18 DeltaPak column)
  4. customBoth diastereomers were separated

Quellen und Nachweise

ORD-Eintrag
ord-d3755facad0444fd917cd8da78946798
Quelldatensatz
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05314902

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