Acetic Acid → HCID 58012042, compound

Participants

Reaction Steps

30 mg (0.052 mmol) of 3-(3-(4-chlorophenyl)-1-[2-(1-methyl-1-[3-(trifluoromethyl)phenyl]ethylamino)-2-oxoethyl]-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-ylmethyl)-benzoic acid (Example 471) are dissolved in 2 ml of THF and treated with 24 mg (0.24 mmol) of triethylamine and 33 mg (0.24 mmol) of isobutyl chloroformate. This is stirred for 1 hr at RT. Next, a solution of 24 mg (0.63 mmol) of sodium borohydride in 0.05 ml water is added slowly. After 1 hr, the mixture is treated with 0.06 ml (1.05 mmol) of acetic acid and then concentrated in vacuo. The residue is taken up in 10 ml of ethyl acetate, and washed with 10 ml of water. The aqueous phase is back-extracted once with 10 ml of ethyl acetate. The combined organic phases are dried over sodium sulphate, filtered and concentrated in vacuo. The crude product is purified by preparative HPLC [Method 10]. 23 mg (79% of theory) of the target compound are thus obtained.

Provenance & Evidence