Dimethyl Sulfoxide → N-(3-formylbenzyl)succinamic acid tert-butyl ester

Temperature

-78 °C

At −78° C., oxalyl chloride (0.142 ml, 1.63 mmol) was added dropwise to a solution of dimethyl sulphoxide (0.232 ml. 3.26 mmol) in dichloromethane (5 ml). The reaction mixture was stirred for 10 min at −78° C. A solution of N-(3-(hydroxymethyl)benzyl)succinamic acid tert-butyl ester (372 mg, 1.55 mmol) in dichloromethane (5 ml) was added. The reaction mixture was stirred at −78° C. for 10 min. Triethylamine (1.08 ml, 7.77 mmol) was added. The reaction mixture was stirred at −78° C. for 5 min and then warmed to room temperature. It was stirred at room temperature for 40 min and diluted with ethyl acetate (100 ml). It was washed with a 10% aqueous solution of sodium hydrogensulphate (100 ml). The aqueous phase was extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (150 ml) and dried over magnesium sulphate. The solvent was removed to give 312 mg of crude N-(3-formylbenzyl)succinamic acid tert-butyl ester, which was used for the next step without further purification.

1. stirringThe reaction mixture was stirred at −78° C. for 10 min
2. stirringThe reaction mixture was stirred at −78° C. for 5 min
3. temperaturewarmed to room temperature
4. stirringIt was stirred at room temperature for 40 min
5. washIt was washed with a 10% aqueous solution of sodium hydrogensulphate (100 ml)
6. extractionThe aqueous phase was extracted with ethyl acetate (2×50 ml)
7. washThe combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (150 ml)
8. dry with materialdried over magnesium sulphate
9. customThe solvent was removed

ORD record

ord-72881dc3276d47b3bbca3fb418ecb9d0

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07524813B2