m-Chloroperbenzoic acid → HCID 58630860, compound

Participants

Reaction Conditions

Reaction Steps

An ice-cold stirred solution of (2S,3R)-3-methoxy-2-(N-cyanomethylamino)-1-(3-quinolylmethanesulfonyl)butane (590 mg) in MDC (20 ml) was treated with 4-toluenesulphonic acid monohydrate (50 mg) and 70% 3-chloroperoxybenzoic acid (281 mg). After 45 min the reaction was quenched with 10% sodium thiosulphate (5 ml) followed by saturated sodium hydrogen carbonate (5 ml) solution. After 5 min the organic layer was collected and the aqueous re-extracted with MDC (10 ml). The combined MDC phases were dried (MgSO4) and evaporated. The residue was redissolved in methanol (10 ml) treated with 4-toluenesulphonic acid monohydrate and hydroxylamine hydrochloride (2.36 g) and heated at 60° C. for 1.5 h. The cooled solution was evaporated, then dissolved in water (5 ml) and saturated sodium hydrogen carbonate solution (5 ml). After extraction with MDC (2×5 ml), the combined extracts were dried (MgSO4) and evaporated. The residue was flash chromatographed (silica gel, step gradient: 80–100% ethyl acetate in hexane) to give the subtitle compound (305 mg). MS (APCI+ve ion) 325(MH+); 1H NMR δ(CDCl3): 8.91 (1H, m), 8.32 (1H, d, J=2 Hz), 8.14 (1H, d, J=8 Hz), 7.85 (1H, d, J=8 Hz), 7.76 (1H, t, J=8 Hz), 7.6 (1H, t, J=8 Hz), 4.83 (1H, broad), 4.58 (2H, m), 3.0–3.7 (4H, m), 3.38 (3H, s), 0.92 (3H, d, J=6.3 Hz).

Provenance & Evidence