반응 #1107614

반응 방정식

triethylamine

dicyclohexylcarbodiimide

dimethylaminopyridine

3-bromo-2-methylbenzoic acid

methyl 6-aminohexanoate hydrochloride

→

title compound

수율 31.2%

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

수율 31.2%

용매

hexane

CH2Cl2

ethyl acetate

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGstirred under a nitrogen atmosphere
3. 3
   기타consumed
4. 4
   기타the reaction was terminated
5. 5
   workup.ADDITIONby adding H2O
6. 6
   추출extracted with CH2Cl2
7. 7
   건조The separated organic layer was dried over MgSO4
8. 8
   기타removed the solvent under a reduced pressure
9. 9
   기타The residue thus obtained

실험 절차

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%).

출처