Sodium borohydride → HCID 68426741, compound

Participants

Reaction Steps

N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}glycyl-L-asparagine (0.020 g, 0.031 mmol) was dissolved in methanol (2 ml). NaBH4 (0.004 g, 0.106 mmol) was added and when the reaction was complete according to LC-MS a few drops of acetic acid were added. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC on a Kromasil C8-column using 35% MeCN in 0.1M ammonium acetate buffer as eluent. After freeze-drying, 0.016 g (80%) of the title product was obtained. NMR (400 MHz, CD3COOD) 2.62 (dd 1H), 2.73 (dd, 1H), 2.90-3.07 (m, 2H), 3.89-4.08 (m, 3H), 4.55 (dd, 1H), 4.60 (ABq, 2H), 4.78-4.85 (m, 1H), 4.90 (d, 0.5H), 4.92 (d, 0.5H), 6.96-7.09 (m, 6H), 7.24-7.38 (m, 6H).

Provenance & Evidence