Thioglycolic Acid → HCID 67272425, compound

Participants

Reaction Steps

To a solution of (3R,5S)-3-{Cyclopropyl-[4-(3-methoxy-propyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-carbamoyl}-5-(2-nitro-benzenesulfonylamino)-piperidine-1-carboxylic acid tert-butyl ester (550 mg, 0.78 mmol) in DMF (5 mL), iodomethane (81 μL, 0.94 mmol) and K2CO3 (320 mg, 2.3 mmol) are added at rt. After stirring overnight, the reaction mixture is diluted with H2O and extracted with EtOAc. The combined organic phases are washed with H2O and dried over Na2SO4. Concentration under reduced pressure and filtration through silica gel give crude product. To a solution of the crude product in DMF (3 mL), thioglycolic acid (160 μL, 2.3 mmol) and LiOH (93 mg, 3.9 mmol) are added at rt. After stirring for 4 hours, the reaction mixture is diluted with H2O and extracted with EtOAc. The combined organic phases are washed with H2O and dried over Na2SO4. Concentration under reduced pressure and filtration through silica gel give the title compound. MS: 545 [M+H]+; tR (HPLC, ACQUITY UPLC™ BEH C18 1.7 μm, 50×2.1 mm; 5% CH3CN+0.1% TFA/H2O+0.1% TFA for 0.5 min then 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 5 min then 100% CH3CN+0.1% TFA for 1.5 min, flow 0.5 ml/min): 3.05 min.

Provenance & Evidence