Lithium hydroxide, monohydrate → HCID 178426999, compound

Participants

Reaction Steps

A mixture of (Z)-3-(1H-benzotriazol-5-yl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]-6-methylbenzoyl]amino]propenoic acid methyl ester trifluoroacetate salt (Example 210; 18 mg, 0.028 mmol) and lithium hydroxide monohydrate (6 mg, 0.144 mmol) in methanol/tetrahydrofuran/water (2:2:1; 0.5 mL) was stirred at room temperature for 125 h. After the volatiles were removed under reduced pressure, the residue was taken up in a mixture of chloroform/methanol/water/acetic acid (150:30:10:6) (10 mL) and evaporated to dryness. The crude product was re-suspended in the same solvent mixture (1 mL) and applied to a column of two piggy-backed SepPak Plus® silica gel cartridges that had been pre-washed with chloroform. The column was eluted with in turn with chloroform, chloroform/methanol/water/acetic acid (600:30:10:6), chloroform/methanol/water/acetic acid (300:30:10:6 and chloroform/methanol/water/acetic acid (150:30:10:6). The appropriate fractions were combined, evaporated and lyophilized to furnish (Z)-3-(1H-benzotriazol-5-yl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]-6-methylbenzoyl]amino]propenoic acid (8.7 mg, 61% yield) as a colorless powder.

Provenance & Evidence