Water → HCID 18318113, compound

Participants

Reaction Steps

To a stirred solution of Intermediate 1d (4 mmol) in DMF (25 mL) at rt was added sodium 2-methyl-2-propanethiolate (2 g, 20 mmol). The resultant suspension was stirred at rt for 18 hr then poured into water (75 mL) and extracted with EtOAc (2×75 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated. Chromatography over silica eluting with 5:95 EtOAc/hexane furnished the N-protected product as a clear colourless oil. The N-Boc-protected sulfide was dissolved in CH2Cl2 (120 mL) and TFA (30 mL) was added. The resultant solution was stirred at rt for 1 hr. Volatiles were removed in vacuo to furnish the title compound as a clear colourless gum (1.34 g, 3.8 mmol). ESI-MS calcd for C15H29NS: 255; found 297 (M+H+MeCN).

Provenance & Evidence