反応 #1107614

反応方程式

triethylamine

dicyclohexylcarbodiimide

dimethylaminopyridine

3-bromo-2-methylbenzoic acid

methyl 6-aminohexanoate hydrochloride

→

title compound

収率 31.2%

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

収率 31.2%

溶媒

hexane

CH2Cl2

ethyl acetate

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGstirred under a nitrogen atmosphere
3. 3
   その他consumed
4. 4
   その他the reaction was terminated
5. 5
   workup.ADDITIONby adding H2O
6. 6
   抽出extracted with CH2Cl2
7. 7
   乾燥The separated organic layer was dried over MgSO4
8. 8
   その他removed the solvent under a reduced pressure
9. 9
   その他The residue thus obtained

実験手順

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%).

出典