Acetonitrile → 5-[2-(2-acetylamino-ethylcarbamoyl)-ethyl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester

5-(2-Carboxy-ethyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 1e (9.85 g, 30.3 mmol) obtained from step 4 of Example 1 was dissolved in acetonitrile (50 ml) under stirring, and added with 1-hydroxy-1H-benzotriazole (8.2 g, 60.6 mmol) and N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide (11.6 g, 60.6 mmol) to the solution at room temperature. Upon completion of the addition, the reaction mixture was stirred at room temperature overnight. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was concentrated under reduced pressure, added with water (200 ml), and exacted with ethyl acetate (200 ml×4). The combined organic extracts were washed with saturated brine (100 ml), dried over anhydrous magnesium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound 5-[2-(2-acetylamino-ethylcarbamoyl)-ethyl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 62a (8 g, yield 65%) as a white solid.

1. additionUpon completion of the addition
2. stirringthe reaction mixture was stirred at room temperature overnight
3. concentrationthe reaction mixture was concentrated under reduced pressure
4. additionadded with water (200 ml)
5. washThe combined organic extracts were washed with saturated brine (100 ml)
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. customto remove the drying agent
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by silica gel column chromatography

ORDレコード

ord-7901a6faa97d4a79bcaebd3206f479c3

出典データセット

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08329682B2