Sodium borohydride → (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2,12-dihydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoic acid

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, methanol (2.0 mL) was added to (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-(2-methoxy-ethyl)-12-oxo-nonadec-4-enoic acid (No. 5444958; 20.0 mg, 0.0302 mmol) and the mixture was cooled to 0° C. While maintaining the temperature at 0° C., sodium borohydride (1.14 mg, 0.0302 mmol) was added and the mixture was stirred for 30 minutes. The reaction was quenched by adding water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated brine, dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off under reduced pressure. The residue was purified by HPLC (water with 0.05% TFA-acetonitrile with 0.05% TFA) to obtain (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2,12-dihydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoic acid (No. 5534088; 11.9 mg, 59% yield).

Provenance & Evidence