Reaktion #52959

Reaktionsgleichung

N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanyl chloride

NaHCO3

NH2OH HCl

→

title compound

Ausbeute 27.2%

N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine N-hydroxyamide

Ausbeute 27.2%

Lösungsmittel

THF

THF water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred overnight at room temperature
2. 2
   SonstigeThe mixture was partitioned between EtOAc and water
3. 3
   WaschenThe EtOAc layer was washed successively with 1 N HCl and brine
4. 4
   Sonstigedried
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe residue was purified by preparative TLC (silica gel; eluent: CH2Cl2/MeOH 8%)

Vorschrift

NaHCO3 (0.21 g) was added to a solution of NH2OH HCl (0.14 g) in THF/water (5 mL each) at 0° C. and the mixture was stirred for ½ h. A solution of N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanyl chloride (0.1 g) in THF (5 mL) was added to the mixture at 0° C. and the mixture was stirred overnight at room temperature. The mixture was partitioned between EtOAc and water. The EtOAc layer was washed successively with 1 N HCl and brine, dried and evaporated. The residue was purified by preparative TLC (silica gel; eluent: CH2Cl2/MeOH 8%) to yield 27 mg of the title compound. ESMS: m/z 489 (MH+).

Quelle