N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-D-alanine → N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-hydroxyethy]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-D-alanine

Participants

Reaction Steps

N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-D-alanine was dissolved in methanol (1.5 ml) whereafter sodium borohydride was added and the mixture was stirred for 30 minutes. After addition of ammonium acetate/H2O solution (2 ml), the methanol was evaporated and the product purified by preparative HPLC (CH3CN/0.1% ammoniumacetate 20:80-100:0). The fractions containing product confirmed by LC-MS were lyophilized and 27 mg (48%) of the desired product was obtained. m/z: 555.0 (M−1).

Provenance & Evidence