Triethylamine → Butyrylamino-acetic acid methyl ester

A suspension of glycine hydrochloride (1.00 g, 7.964 mmol) in methylene chloride (40 mL), cooled to 0° under a nitrogen atmosphere, was treated with triethylamine (4.44 mL, 31.86 mmol) and butyryl chloride (0.93 mL, 8.76 mmol), and the mixture stirred at room temperature for 2.5 hours. The reaction was washed with saturated aqueous sodium bicarbonate (50 mL), water (50 mL) and brine. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum giving the title compound. Purification by silica gel flash chromatography with 25% ethyl acetate/methylene chloride afforded the title compound as a colorless oil (0.776 g, 4.88 mmol, 61%).

1. temperaturecooled to 0° under a nitrogen atmosphere
2. washThe reaction was washed with saturated aqueous sodium bicarbonate (50 mL), water (50 mL) and brine
3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated under vacuum

ORD record

ord-529758c4958749dd820eecee4341064e

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07915411B2