Valproic Acid → (R)-N5-[Amino(nitroimino)methyl]-N-[(4-hydroxyphenyl)methyl]-N2-(1-oxo-2-propylpentyl)-ornithinamide

HRID 52591

Reaktionsgleichung

Reaktionsgleichung von HRID 52591
[NH2:1][C:2](=[N:20][N+:21]([O-:23])=[O:22])[NH:3][CH2:4][CH2:5][CH2:6][C@H:7]([C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)=[O:10])[NH2:8].[CH2:24]([CH:27]([CH2:31][CH2:32][CH3:33])[C:28](O)=[O:29])[CH2:25][CH3:26].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>O1CCCC1>[NH2:1][C:2](=[N:20][N+:21]([O-:23])=[O:22])[NH:3][CH2:4][CH2:5][CH2:6][C@H:7]([C:9]([NH:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=1)=[O:10])[NH:8][C:28](=[O:29])[CH:27]([CH2:31][CH2:32][CH3:33])[CH2:24][CH2:25][CH3:26]

Komponenten

5

Edukt 3

HCID 3121Valproic AcidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 136381090(R)-N5-[amino(nitroimino)methyl]-N-[(4-hydroxyphenyl)methyl)-ornithinamide

Produkt 1

HCID 136381110(R)-N5-[Amino(nitroimino)methyl]-N-[(4-hydroxyphenyl)methyl]-N2-(1-oxo-2-propylpentyl)-ornithinamideAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Prepared analogously to Example 5d), but using tetrahydrofuran instead of acetonitrile, from (R)-N5 -[amino(nitroimino)methyl]-N-[(4-hydroxyphenyl)methyl]-ornithinamide, 2-propyl-pentanoic acid and TBTU in a yield of 65% of theory. Colourless crystalline substance which was further processed without purification.

Aufarbeitung

  1. customPrepared analogously to Example 5d), but
  2. customColourless crystalline substance which was further processed without purification

Quellen und Nachweise

ORD-Eintrag
ord-6015da7a28fd4a88b0e39061f1a3dbc5
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616620

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