Toluene → HCID 10257257, compound

Participants

Reaction Steps

To a solution of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.51 g) in dimethyl sulfoxide (2 mL), toluene (4 mL) and dichloroacetic acid (0.14 g) was added 2-[3-benzyloxycarbonyl-amino-5-(3-fluorobenzyl)-2-oxo-1,2-dihydro-1-pyridyl]-N-(3,3,3-trifluoro-2-hydroxy-1-isopropylpropyl)acetamide (0.15 g). The mixture was allowed to stir overnight and was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organics were washed (brine), dried, evaporated, and purified using chromatography, with dichloromethane as the eluent to yield the title compound (80%); NMR: 0.79-0.97 (m,6), 2.21 (m,1), 4.06 (m, NHCH hydrate), 4.49-4.81 (m,3, NHCH keto, CH2CO), 5.13 (s,2, CH2), 6.95 (m, OH hydrate), 7.01-7.07 (m,3, phenyl), 7.22-7.40 (m,7, phenyl), 7.72 (m,1, pyridone), 7.82 (d,J=10.5, NH hydrate), 8.36 (s, NH hydrate), 8.40 (s, NH keto), 8.92 (d,J=6.5, NH keto form).

Provenance & Evidence