Water → 3-(4-Formylbenzoylamino)propionic acid methyl ester

4-formyl-benzoic acid (20 g, 133 mmol), CDMT (24 g, 137 mmol), and 4-methyl-morpholine (15.4 mL, 140 mmol) are combined in anhydrous dichloromethane (DCM) (300 mL) under nitrogen. The reaction is allowed to stir under nitrogen at room temperature overnight. Beta-alanine methyl ester hydrochloride (20.4 g, (147 mmol) is then added to the reaction mixture, followed by 4-methylmorpholine (15.4 mL, 140 mmol), and allowed to stir at room temperature. Some water (<10% volume) is added to help solubility. The reaction is monitored by HPLC, and upon complete consumption of the acid, the reaction is diluted with DCM. The reaction is diluted with water and extracted with 1N HCl. The organic layer is washed with water and brine, followed by drying over anhydrous sodium sulfate. The solution is filtered and concentrated and further purified using flash column chromatography (30 g, 128 mmol).

1. stirringto stir at room temperature
2. customupon complete consumption of the acid
3. additionthe reaction is diluted with DCM
4. additionThe reaction is diluted with water
5. extractionextracted with 1N HCl
6. washThe organic layer is washed with water and brine
7. dry with materialby drying over anhydrous sodium sulfate
8. filtrationThe solution is filtered
9. concentrationconcentrated
10. customfurther purified

ORD record

ord-e027258576ef4d19b34d3a87fce29845

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07816557B2