Dimethyl Sulfoxide → tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

Temperature

-78 °C

To dimethyl sulfoxide (2.82 mL, 39.8 mmol) dissolved in anhydrous methylene chloride (5 mL) and cooled to -78° C. was added dropwise oxalyl chloride (2.6 mL, 1.5 equiv). After 10 minutes at -78° C., N-Boc-Phenylalaninol (5.00 g, 19.9 mmol) dissolved in anhydrous methylene chloride (75 mL) was cannulated into the reaction mixture. After 15 minutes at -78° C., the reaction was stirred for 2 minutes at 0° C. and then cooled again to -78° C. Triethylamine (11.9 mL, 4.3 equiv) was added dropwise. After 25 minutes, the reaction was quenched with cooled 10% citric acid (15 mL) and then diluted with additional 10% citric acid (75 mL). Ether (300 mL) was added and the solution was washed with water (5×100 mL), brine, water (5×100 mL), and brine, dried over sodium sulfate, and concentrated under reduced pressure to afford the title compound (4.22 g).

1. waitAfter 15 minutes at -78° C.
2. temperaturecooled again to -78° C
3. waitAfter 25 minutes
4. customthe reaction was quenched
5. temperaturewith cooled 10% citric acid (15 mL)
6. additiondiluted with additional 10% citric acid (75 mL)
7. additionEther (300 mL) was added
8. washthe solution was washed with water (5×100 mL), brine, water (5×100 mL), and brine
9. dry with materialdried over sodium sulfate
10. concentrationconcentrated under reduced pressure

ORD record

ord-46b9dcaa23c84ce78fede13002558d99

Source dataset

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05648497