Reaction #433637

Reaction equation

8-(3-fluoro-benzyloxy)-1,3-dihydro-benzo[d]azepin-2-one

triethylamine

methoxyacetic acid chloride

→

8-(3-fluoro-benzyloxy)-3-methoxyacetyl-1,3-dihydro-benzo[d]azepin-2-one

Yield 24.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Othercontinued at 0° C
2. 2
   workup.WAITThe reaction mixture was left
3. 3
   Temperatureto warm to RT
4. 4
   workup.STIRRINGstirring
5. 5
   Otherthe reaction mixture was evaporated under reduced pressure
6. 6
   OtherFor purification
7. 7
   Otherthe crude material obtained
8. 8
   Otherchromatographed on silica gel using a 99

Procedure

In a dried flask under an inert atmosphere, 50 mg (0.18 mmol) of 8-(3-fluoro-benzyloxy)-1,3-dihydro-benzo[d]azepin-2-one were dissolved in 3 ml of dichloromethane, and the solution cooled to 0° C. Thereupon, 21 mg (0.21 mmol) triethylamine were added and stirring continued at 0° C. Finally, 18 μl (0.2 mmol) of methoxyacetic acid chloride were added. The reaction mixture was left to warm to RT and stirring continued for 18 h. For the working-up, the reaction mixture was evaporated under reduced pressure. For purification, the crude material obtained was directly transferred on a column and chromatographed on silica gel using a 99:1-mixture of dichloromethane and methanol as the eluent. There were obtained 15 mg (24% of theory) of 8-(3-fluoro-benzyloxy)-3-methoxyacetyl-1,3-dihydro-benzo[d]azepin-2-one as a white powder; MS: m/e=356 (M+H)+.

Source