tert-Butyldimethylsilyl chloride → HCID 86602441, compound

Participants

Reaction Steps

Methyl (4R)-1-(1,1′-biphenyl-4-ylcarbonyl)-4-hydroxy-L-prolinate (intermediate 2a, 2.07 g, 6.35 mmol) was dissolved in DCM (30 ml) and treated with 4-DMAP (776 mg, 6.35 mmol), TEA (2.21 ml, 15.88 mmol) and TBDMS-Cl (1.91 g, 12.7 mmol). The reaction was monitored by LC/MS. After 24 h, as the reaction was not completed, TBDMS-CL (300 mg, 2 mmol) and TEA (1 ml) were added. After 48 h, the reaction was completed. The mixture was washed with sat. NH4Cl and brine (twice), dried over magnesium sulfate, filtered and concentrated. The crude (2.85 g) was purified by flash chromatography using EtOAc/cHex 50:50 as eluant.

Provenance & Evidence