Triethylamine → (S)-2-(2-amino-5-methoxy-benzoylamino)-hexanoic acid methyl ester

HRID 388479

Reaktionsgleichung

Reaktionsgleichung von HRID 388479
[CH3:1][O:2][C:3]1[CH:14]=[C:7]2[C:8]([O:10]C(=O)[NH:12][C:6]2=[CH:5][CH:4]=1)=O.Cl.[CH3:16][O:17][C:18](=[O:25])[C@@H:19]([NH2:24])[CH2:20][CH2:21][CH2:22][CH3:23].C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[CH3:16][O:17][C:18](=[O:25])[C@@H:19]([NH:24][C:8](=[O:10])[C:7]1[CH:14]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[NH2:12])[CH2:20][CH2:21][CH2:22][CH3:23]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 2944796-methoxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dioneHCID 14039065methyl (2S)-2-aminohexanoate hydrochloride

Produkt 1

HCID 68727802(S)-2-(2-amino-5-methoxy-benzoylamino)-hexanoic acid methyl esterAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 5-methoxy-isatoic anhydride (1.0 g, 5.18 mmol) and (S)-2-amino-hexanoic acid methyl ester hydrochloride (1.4 g, 7.71 mmol) (prepared according to example A) in DMF (10 mL) is added triethylamine (2.0 mL, 11.48 mmol). The mixture is stirred at room temperature for 16 hours. The reaction mixture is diluted with EtOAc (100 mL) and washed with H2O (50 mL×3). The organic layer is dried over sodium sulfate, concentrated and the residue is purified by flash chromatography with 60% EtOAc in Hexane as the eluent to afford (S)-2-(2-amino-5-methoxy-benzoylamino)-hexanoic acid methyl ester (410 mg, 27%).

Aufarbeitung

  1. washwashed with H2O (50 mL×3)
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationconcentrated
  4. customthe residue is purified by flash chromatography with 60% EtOAc in Hexane as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-b0d3c116923244c6922301272b5d72f6
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377949B2

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