Sodium Hydroxide → 5-[(3S*,4S*,5R*)-5-(3-tert-Butyl-benzylamino)-4-hydroxy-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-3-ylmethyl]-2-nitro-benzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-[(3S*,4S*,5R*)-5-(3-tert-butyl-benzylamino)-4-hydroxy-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-3-ylmethyl]-2-nitro-benzoic acid methyl ester (434 mg, 0.86 mmol; prepared from methyl 5-(bromomethyl)-2-nitrobenzoate using a procedure analogous to that used in example 1) and NaOH (30% in H2O, 1 mL, 7.4 mmol) in anhydrous THF (5 mL) was stirred at 80° C. for 1 h. The reaction mixture was diluted with EtOAc and quenched with 2N aq. HCl to pH 2. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated to yield the product as a yellow gum: ESIMS [M+H]+=491, LCMS RtI=0.97 min.

Provenance & Evidence