D-1,4-Dithiothreitol → HCID 10786892, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of [4-(cyanothio)-5-(1,1-dimethylethyl)-2-methylphenyl]-imidodicarbonic acid bis(1,1-dimethylethyl) ester obtained in Example EEEE (11.65 g, 27.7 mmol) in denatured EtOH (160 mL) was added dithiothreitol (16.8 g, 109.1 mmol), and 0.2 M KH2PO4 solution (40 mL). The mixture was stirred overnight at 50° C. The solvent was evaporated, and H2O and CHCl3 were added; the organic layer was washed with brine, dried (Na2SO4) filtered and concentrated. The resulting residue was flash chromatographed on silica gel, eluting with 1:1 CHCl3 :hexanes switching to 19:1 CHCl3 :EtOAc, to afford the title compound. 1H NMR (CDCl3) δ 1.40-1.46 (m, 27 H), 2.07 (s, 3 H), 7.00 (s, 1 H), 7.05 (s, 1 H).

Provenance & Evidence