4-Methylmorpholine → 3(S)-(Pyridin-3-yl)-3-(5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-pentanoylamino)propionic acid ethyl ester

HRID 1004237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1004237
Cl.[N:2]1[C:11]2[NH:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O.F[P-](F)(F)(F)(F)F.[N:26]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34]C=2N=N1.[CH3:46][N:47]1CCOCC1.[C:53]([O:56][CH2:57][CH3:58])(=[O:55])[CH3:54]>CC#N>[CH2:57]([O:56][C:53](=[O:55])[CH2:54][C@@H:46]([C:33]1[CH:34]=[N:26][CH:30]=[CH:31][CH:32]=1)[NH:47][C:16](=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][NH:10][C:11]=2[N:2]=1)[CH3:58]

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 697750595-(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)pentanoic acid hydrochloride

Produkt 1

HCID 544418963(S)-(Pyridin-3-yl)-3-(5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-pentanoylamino)propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 1-6 (50 mg, 0.1847 mmol), 1-7 (49 mg, 0.1847 mmol) (Rico et al., J. Org. Chem., 1993, 58, 7948), BOP (90 mg, 0.2032 mmol) and NMM (0.122 mL, 1.11 mmol) in CH3CN (2 mL) was stirred for 18 h. The mixture was diluted with ethyl acetate, washed with sat. NaHCO3, brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 20% MeOH/ethyl acetate) to give 1-8 as a yellow oil.

Aufarbeitung

  1. washwashed with sat. NaHCO3, brine
  2. dry with materialdried over MgSO4
  3. customremoval of the solvent
  4. customthe residue was chromatographed (silica gel, 20% MeOH/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d7d7933649114619b089c8bd6b8cb493
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06048861

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