Hydrogen Peroxide → (R)-methyl 5-(sec-butylamino)-4-(aminocarbonyl)-2-methylbenzoate

HRID 906155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 906155
[C@H:1]([NH:5][C:6]1[C:7]([C:17]#[N:18])=[CH:8][C:9]([CH3:16])=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12])([CH2:3][CH3:4])[CH3:2].OO.C(=O)([O-])[O-:22].[K+].[K+]>CS(C)=O>[C@H:1]([NH:5][C:6]1[C:7]([C:17]([NH2:18])=[O:22])=[CH:8][C:9]([CH3:16])=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12])([CH2:3][CH3:4])[CH3:2]

Komponenten

5

Edukt 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 67404849(R)-methyl 5-(sec-butylamino)-4-cyano-2-methylbenzoate

Produkt 1

HCID 67403610(R)-methyl 5-(sec-butylamino)-4-(aminocarbonyl)-2-methylbenzoateAusbeute 282,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a cooled (0° C.) solution of (R)-methyl 5-(sec-butylamino)-4-cyano-2-methylbenzoate (300 mg, 1.22 mmol) in DMSO (1.5 mL) was added 30% hydrogen peroxide solution (258 μL, 8.96 mmol) and potassium carbonate (56 mg, 0.402 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 4 h, at which time it was concentrated in vacuo. The residue was purified by flash chromatography (100% hexanes to 10% ethyl acetate in hexanes) to afford (R)-methyl 5-(sec-butylamino)-4-(aminocarbonyl)-2-methylbenzoate (300 mg, 93%) as yellow crystals. MS (EI) for C14H20N2O3: 265 (MH+).

Aufarbeitung

  1. concentrationwas concentrated in vacuo
  2. customThe residue was purified by flash chromatography (100% hexanes to 10% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-911c5838e0c241a39be6efb43077efc7
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012956B2

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