Sodium Bicarbonate → tert-Butyl 2-methyl-2-[4-({[(4-methyl-1,3-oxazol-5-yl)methyl]amino}methyl)-phenoxy]-propanoate

HRID 1266527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1266527
[CH:1]([C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]([CH3:17])([CH3:16])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:5][CH:4]=1)=O.[CH3:20][C:21]1[N:22]=[CH:23][O:24][C:25]=1[CH2:26][NH2:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl>[CH3:16][C:8]([O:7][C:6]1[CH:18]=[CH:19][C:3]([CH2:1][NH:27][CH2:26][C:25]2[O:24][CH:23]=[N:22][C:21]=2[CH3:20])=[CH:4][CH:5]=1)([CH3:17])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Komponenten

6

Edukt 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 22708193tert-Butyl 2-(4-formylphenoxy)-2-methylpropanoateHCID 22708194(4-Methyl-1,3-oxazol-5-yl)methylamine

Produkt 1

HCID 22708253tert-Butyl 2-methyl-2-[4-({[(4-methyl-1,3-oxazol-5-yl)methyl]amino}methyl)-phenoxy]-propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

1.25 g (4.73 mmol) of tert-butyl 2-(4-formylphenoxy)-2-methylpropanoate (Example I-4) and 0.64 g (5.67 mmol) of (4-methyl-1,3-oxazol-5-yl)methylamine (Example III-28) are together initially charged in 1,2-dichloroethane. At room temperature, 1.50 g (7.09 mmol) of sodium triacetoxyborohydride are added. The reaction mixture is stirred at room temperature for 4 hours and then admixed with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulphate and freed from the solvent under reduced pressure. The residue is purified chromatographically on silica gel (dichloromethane/methanol 30:1) and then dried under reduced pressure. This gives 1.104 g (65% of theory) of the title compound.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. customThe residue is purified chromatographically on silica gel (dichloromethane/methanol 30:1)
  4. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-336253dcd7664259adace0fb5fed48d3
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06548538B2

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