tert-Butyl acetate → TERT-BUTYL (S)-4-(CBZ-AMINO)-5-METHYL-3-OXOHEXANOATE

Participants

Reaction Steps

To an ice-cooled solution of Z-Valine (5 g, 19.9 mmol) in 60 ml tetrahydrofuran was added N,N'-carbonyldiimidazole (3.55 g, 22.3 mmol) in one portion and the resulting mixture stirred for 3 h. t-Butyl acetate (13.5 ml, 100 mmol) was added dropwise to a solution of LDA (90 mmol in tetrahydrofuran (270 ml) at -78° C. After 30 min, the imidazolide solution was added dropwise via double-ended needle to the enolate. The resulting mixture was stirred for 2 h until the temperature rose to -15° C. The reaction was quenched with 400 ml saturated aqueous NH4Cl and extracted with ether (3×200 ml). The combined organic extracts were washed with 2N aqueous HCl (50 ml), saturated aqueous NaHCO3 (2×50 ml), dried over magnesium sulfate and evaporated to dryness in vacuo. The residue was purified by column chromatography on silica gel using ethyl acetate-hexane (1:4) as an eluent to give the product as a colorless oil (6.88 g).

Provenance & Evidence