Dimethyl Sulfoxide → 3-[Benzyloxycarbonyl-(2-oxo-ethyl)-amino]-propionic acid tert-butyl ester

Temperature

0 °C

To a solution of 4.53 ml (35.65 mmol) of oxalyl chloride in 76 ml dichloromethane at −50 to −60° C. was added a solution of 5.81 ml (74.40 mmol) dimethylsulfoxide in 16 ml of dichloromethane within 20 min. The solution was stirred for 5 min and a solution of 10.03 g (31.0 mmol) 3-[benzyloxycarbonyl-(2-hydroxy-ethyl)-amino]-propionic acid tert-butyl ester in 67 ml dichloromethane was added within 20 min. The mixture was stirred for 15 min and 21.6 ml (155 mmol) of triethylamine were added within 25 min. The suspension was stirred for 2 h and slowly warmed to 0° C. The reaction was neutralized with cold 10% aq. potassium dihydrogenphosphate solution (adjusted with solid potassium dihydrogenphosphate to pH 4-5) and extracted with diethyl ether (3×). The organic phases were washed with 10% aq. potassium dihydrogenphosphate solution, sat. aq. sodium hydrogencarbonate solution, 10% aq. sodium chloride solution, dried over Na2SO4 evaporated to yield 9.94 g (99.8%) of the title compound as yellow oil. MS: 322.1 (MH+).

1. stirringThe mixture was stirred for 15 min
2. stirringThe suspension was stirred for 2 h
3. extractionextracted with diethyl ether (3×)
4. washThe organic phases were washed with 10% aq. potassium dihydrogenphosphate solution, sat. aq. sodium hydrogencarbonate solution, 10% aq. sodium chloride solution
5. dry with materialdried over Na2SO4
6. customevaporated

ORD record

ord-8e009111ef2747518c27ecce39abf158

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071586B2