4-Fluorobenzylamine → HCID 448749, Verbindung

HRID 2426268Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2426268
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[OH:10][C:11]1[C:30](=[O:31])[N:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]([NH:21][C@@H:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH3:23])[C:14]2=[N:13][C:12]=1[C:32](OC)=[O:33]>CO>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:32]([C:12]2[N:13]=[C:14]3[CH:20]([NH:21][C@@H:22]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH3:23])[CH2:19][CH2:18][CH2:17][CH2:16][N:15]3[C:30](=[O:31])[C:11]=2[OH:10])=[O:33])=[CH:4][CH:3]=1.[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH3+:7])=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 673264-FluorobenzylamineHCID 67148233HCID 67148233, Verbindung

Produkt 2

HCID 448749HCID 448749, VerbindungHCID 67148197HCID 67148197, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

p-Fluorobenzylamine (3 eq.) was added to the methyl 3-hydroxy-4-oxo-10-{[(1R)-1-phenylethyl]amino}-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepine-2-carboxylate (prepared as described in Step 5 or Step 5A) dissolved in methanol. The mixture was stirred at 70° C. overnight, then cooled to room temperature for use directly in Step 7. In an alternative procedure (Step 6A), the solvent was removed and the crude product crystallized from acetonitrile several times to obtain a single diastereoisomer of the title compound as the 4-fluorobenzylammonium salt with d.e.>95%

Aufarbeitung

  1. temperaturecooled to room temperature for use directly in Step 7
  2. customIn an alternative procedure (Step 6A), the solvent was removed
  3. customthe crude product crystallized from acetonitrile several times

Quellen und Nachweise

ORD-Eintrag
ord-db0f0a347e26408f89a81faed7481ae6
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968553B2

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