Triethylamine → HCID 67350582, compound

Participants

Reaction Steps

(S)-3-(9-Methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzoic acid (150 mg, 0.405 mmol) obtained in Step 1 of Example 56 was dissolved in dichloromethane (5 mL), and the mixture was stirred for 4 hours after adding L-serine methyl ester hydrochloride (95.0 mg, 0.607 mmol), triethylamine (0.0850 mL, 0.607 mmol), 1-ethyl-3-(3dimethylaminopropyl)carbodiimide hydrochloride (93.0 mg, 0.486 mmol), and 1-hydroxybenzotriazole.monohydrate (62.0 mg, 0.405 mol). The mixture was diluted with chloroform and washed with a saturated aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was dissolved in THF (5 mL), and the mixture was stirred at room temperature for 30 minutes after adding triphenylphosphine (212 mg, 0.810 mmol) and a 40% toluene solution of diethyl azodicarboxylate (0.367 mL, 0.810 mmol). The mixture was concentrated, and the resulting residue was purified by silica gel column chromatography to give methyl (S)-2-{3-[(S)-9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl]phenyl}-4,5-dihydro-1,3-oxazole-4-carboxylate (138 mg, 75%).

Provenance & Evidence