1,2-Ethanediamine, N1,N1,N2-trimethyl- → HCID 71138290, compound

Participants

Reaction Steps

To a solution of (S)-4-benzyl-3-(4-(benzyloxy)butanoyl)oxazolidin-2-one (170 g, 482 mmol) in THF (1.0 L) at −78° C. was added LiHMDS (1.0 M in THF, 530 mL, 530 mmol) over 10 minutes via cannula. After stirring for 1 h at −78° C. tert-butyl bromoacetate (82.0 mL, 554 mmol) was added slowly over 45 min via syringe pump. The mixture was slowly allowed to warm to room temperature overnight. The reaction mixture was quenched with sat. ammonium chloride (300 mL) and stirred for 10 min, diluted further with H2O (500 mL), and extracted with MTBE (1.0 L). The organic layer was isolated, treated with N,N,N′-trimethylethylenediamine (5 mL) and shaken for 2 min in order to remove excess tert-butyl bromoacetate. The mixture was washed with 1 N HCl (2×750 mL), and brine (1.0 L). The organics were dried over MgSO4, filtered, and concentrated to give 262 g of crude (R)-tert-butyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-5-(benzyloxy)pentanoate.

Provenance & Evidence