4-Methylmorpholine → HCID 15481806, Verbindung

HRID 887947Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 887947
[C:1]1([CH2:7][CH2:8][CH2:9][C@H:10]([C@@H:14]([N:16]([CH:24]=[O:25])[O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH3:15])[C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[CH3:70][NH:71][C:72](=[O:79])[C@@H:73]([NH2:78])[C:74]([CH3:77])([CH3:76])[CH3:75]>CN(C=O)C>[CH3:75][C:74]([CH3:77])([CH3:76])[C@H:73]([NH:78][C:11](=[O:13])[C@H:10]([CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C@@H:14]([N:16]([CH:24]=[O:25])[O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)[CH3:15])[C:72](=[O:79])[NH:71][CH3:70]

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 445856(2S)-2-Amino-N,3,3-trimethylbutanamideHCID 11245009HCID 11245009, Verbindung

Produkt 1

HCID 15481806HCID 15481806, VerbindungAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (2R,3S)-2-(3-phenyl-1-propyl)-3-(formyl-2-tetrahydropyranyloxyamino)buta noic acid (5.5 g, 15.76 mmol) in DMF (20 mL) is added BOP reagent (7.66 g, 17.34 mmol), HOBt (2.34 g, 17.34 mmol), and NMM (4.78 g, 47.28 mmol). After 30 min, addition of (2S)-2-Amino-3,3-dimethylbutanoic acid methylamide (3.4 g, 23.64) occurs and the resulting solution is stirred at 25.degree. C. for 20 h. The reaction mixture is poured into ethyl acetate/hexanes (1:1, 200 mL) and washed sequentially with 1 M hydrochloric acid, 1 M aqueous sodium carbonate, and saturated aqueous sodium chloride. The organic layer is dried over magnesium sulfate, concentrated in vacuo, and purified by silica gel chromatography (elution with 2:1 ethyl acetate-hexane) to provide (2R,3S)-3-(Formyl-2-tetrahydropyranyloxyamino)-2-(3-phenyl-1-propyl)butanoic acid [(1S)-2,2-dimethyl-1-(methylcarbamoyl)-1-propyl]amide as a white solid (2.7 g, 36% yield).

Aufarbeitung

  1. waitfor 20 h
  2. washwashed sequentially with 1 M hydrochloric acid, 1 M aqueous sodium carbonate, and saturated aqueous sodium chloride
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel chromatography (elution with 2:1 ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-8238f65127384d59aaf113dbc7225e74
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247451B2

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