4-Methylmorpholine → HCID 11478231, Verbindung

HRID 2269346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2269346
[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.Cl.Cl.[N:72]1[CH:77]=[CH:76][CH:75]=[C:74]([NH:78][C:79](=[O:86])[C@@H:80]([NH2:85])[C:81]([CH3:84])([CH3:83])[CH3:82])[CH:73]=1>CN(C=O)C>[CH3:82][C:81]([CH3:84])([CH3:83])[C@H:80]([NH:85][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:79](=[O:86])[NH:78][C:74]1[CH:73]=[N:72][CH:77]=[CH:76][CH:75]=1

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 11245009HCID 11245009, VerbindungHCID 70212260HCID 70212260, Verbindung

Produkt 1

HCID 11478231HCID 11478231, VerbindungAusbeute 62,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of (2R,3S)-2-(3-phenyl-1-propyl)-3-(formyl-2-tetrahydropyrariyloxyamino)butanoic acid (120 mg, 0.344 mmol) in DMF (1 mL) is added BOP reagent (167 mg, 0.378 mmol), HOBt (51 mg, 0.378 mmol), and NMM (174 mg, 1.72 mmol). After 30 min, (2S)-2-amino-3,3-dimethylbutanoic acid 3-pyridylamide dihydrochloride (118 mg, 0.410) is added and the resulting solution is stirred at 25° C. for 18 h. The reaction mixture is concentrated, diluted with EtOAc (20 mL) and washed sequentially with 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 EtOAc-hexane) to provide (2R,3S)-3-(formyl-2-tetrahydropyranyloxyamino)-2-(3-phenyl-1-propyl)butanoic acid [(1S)-2,2-dimethyl-1-(3-pyridylcarbamoyl)-1-propyl]amide as a solid (115 mg, 62% yield). ESI-MS m/z 529 (M+H)+.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated
  2. additiondiluted with EtOAc (20 mL)
  3. washwashed sequentially with 1 M aqueous sodium carbonate and saturated aqueous sodium chloride
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel chromatography (elution with 2:1 EtOAc-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-fade9af093a64ab393021f216af59083
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06329400B1

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