Reacción #1107614

Ecuación de reacción

triethylamine

dicyclohexylcarbodiimide

dimethylaminopyridine

3-bromo-2-methylbenzoic acid

methyl 6-aminohexanoate hydrochloride

→

title compound

Rendimiento 31.2%

methyl 6-(3-bromo-2-methylbenzamido)hexanoate

Rendimiento 31.2%

Disolventes

hexane

CH2Cl2

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGstirred under a nitrogen atmosphere
3. 3
   Otroconsumed
4. 4
   Otrothe reaction was terminated
5. 5
   workup.ADDITIONby adding H2O
6. 6
   Extracciónextracted with CH2Cl2
7. 7
   SecadoThe separated organic layer was dried over MgSO4
8. 8
   Otroremoved the solvent under a reduced pressure
9. 9
   OtroThe residue thus obtained

Procedimiento

1.27 g of methyl 6-aminohexanoate hydrochloride (6.98 mmol) was dissolved in 25 ml of CH2Cl2 with stirring. 941 mg of triethylamine (9.3 mmol, 1.3 ml) was added to the mixture, and dicyclohexylcarbodiimide (DCC; 1.15 g, 5.58 mmol), dimethylaminopyridine (DMAP; 56.8 mg, 10 mol %), and 3-bromo-2-methylbenzoic acid (1.00 g, 4.65 mmol) was added thereto and stirred under a nitrogen atmosphere. After 24 hrs, the resulting mixture was subjected to thin layer chromatography to monitor the amount of the starting materials consumed, and the reaction was terminated by adding H2O thereto and extracted with CH2Cl2. The separated organic layer was dried over MgSO4 and removed the solvent under a reduced pressure. The residue thus obtained was subjected to a column chromatography (hexane:ethyl acetate=1:1, v/v) to obtain the title compound (497 mg, 31%).

Fuente