Ethanolamine → HCID 58109728, Verbindung

HRID 2037468Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2037468
CS(O[CH2:6][CH2:7][C@@:8]1([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[F:30])=[CH:19][CH:18]=2)[CH3:16])[CH2:10][CH2:9]1)(=O)=O.[NH2:38][CH2:39][CH2:40][OH:41]>CO>[F:30][C:24]1[CH:25]=[C:26]([F:29])[CH:27]=[CH:28][C:23]=1[C:20]1[CH:21]=[CH:22][C:17]([C@@H:15]([N:11]2[CH2:10][CH2:9][C@@:8]([C:31]3[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=3)([CH2:7][CH2:6][NH:38][CH2:39][CH2:40][OH:41])[O:13][C:12]2=[O:14])[CH3:16])=[CH:18][CH:19]=1

Komponenten

4

Edukt 2

HCID 700EthanolamineHCID 86649947HCID 86649947, Verbindung

Produkt 1

HCID 58109728HCID 58109728, VerbindungAusbeute 3,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2-((S)-3-((S)-1-(2′,4′-difluorobi-phenyl-4-yl)ethyl)-6-(4-fluorophenyl)2-oxo 1,3-oxazinan-6-yl)ethyl methanesulfonate (58 mg, 0.11 mmol) in anhydrous MeOH was added 2-amino-ethanol (54 mg, 0.88 mmol). Then the reaction mixture was refluxed overnight. When the reaction was over, solvent was removed in vacuo. The residue was purified by preparative HPLC to give (R)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-6-(2-(2-hydroxyethylamino)ethyl)-1,3-oxazinan-2-one (2 mg, 3%). 1H NMR (CDCl3): 1.53 (m, 3H), 2.25-2.36 (m, 4H), 2.51 (m, 1H), 2.87-3.24 (m, 5H), 3.75-4.02 (m, 2H), 5.60 (m, 1H), 6.85-6.96 (m, 2H), 6.96-7.10 (m, 4H), 7.22 (m, 2H), 7.38 (m, 4H).

Aufarbeitung

  1. temperatureThen the reaction mixture was refluxed overnight
  2. customwas removed in vacuo
  3. customThe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-fa74a4ec76744f01955af90c8042d722
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575156B2

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