반응 #84833

반응 방정식

N,O-Dimethylhydroxylamine HCl

2-methoxy-2-(4-(2-methyl-2H-tetrazol-5-yl)phenyl)acetic acid

N,N-diisopropylethylamine

NaHCO3

bis(2-Methoxyethyl)aminosulfur trifluoride

→

N,2-dimethoxy-N-methyl-2-(4-(2-methyl-2H-tetrazol-5-yl)phenyl)acetamide

수율 42.0%

용매

CH2Cl2

반응 조건

후처리

1. 1
   온도while cooling over an ice bath
2. 2
   workup.STIRRINGto stir overnight
3. 3
   workup.STIRRINGstirred for 5 min
4. 4
   건조The organic layer was dried over Na2SO4
5. 5
   기타evaporated to dryness
6. 6
   기타Purification by chromatography (60% EtOAc-hexanes)

실험 절차

To a solution of 2-methoxy-2-(4-(2-methyl-2H-tetrazol-5-yl)phenyl)acetic acid (0.87 g, 3.5 mmol) in anhydr CH2Cl2 (10 ml) was added N,N-diisopropylethylamine (1.36 g, 10.5 mmol) while cooling over an ice bath. bis(2-Methoxyethyl)aminosulfur trifluoride (0.93 g, 4.2 mmol) was added and stirred 15 min. N,O-Dimethylhydroxylamine HCl (0.512 g, 5.25 mmol) was added and the mixture was allowed to stir overnight while warming to room temp. Saturated aqueous NaHCO3 (15 ml) was added and stirred for 5 min. The organic layer was dried over Na2SO4 and evaporated to dryness. Purification by chromatography (60% EtOAc-hexanes) gave N,2-dimethoxy-N-methyl-2-(4-(2-methyl-2H-tetrazol-5-yl)phenyl)acetamide as a clear oil (0.425 g, 42% yield).

출처