Potassium Iodide → HCID 71254893, compound

Participants

Reaction Conditions

Reaction Steps

A sealed tube containing a suspension of Intermediate 39A (0.500 g, 2.340 mmol), potassium carbonate (0.485 g, 3.51 mmol), potassium iodide (0.039 g, 0.234 mmol), and tert-butyl bromoacetate (0.415 ml, 2.81 mmol) in DMA (4.68 mL) was warmed to 100° C. After 3 h, additional tert-butyl bromoacetate (0.415 mL, 2.81 mmol) was added and the reaction was heated at 100° C. After 22 h, the reaction was stopped and cooled to rt. The reaction was filtered, eluting with diethyl ether. The filtrate was partitioned between diethyl ether and water and the layers were separated. The aqueous layer was extracted with diethyl ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to give a clear, yellow liquid weighing 1.35 g. Purification by normal phase chromatography gave 1.2:1 mixture of Intermediate 39A and methyl 2-(2-(tert-butoxy)-2-oxoethyl)(3-chlorophenyl)amino)propanoate (0.375 g) as a clear, colorless viscous oil. MS (ESI) m/z: 350.0 (M+Na)+. A clear, colorless solution of Intermediate 39A and methyl 2-((2-(tert-butoxy)-2-oxoethyl)(3-chlorophenyl)amino)propanoate (0.375 g, 1.144 mmol) in 50% TFA/DCM (16.34 mL) was stirred at rt. After 3 h, the reaction was concentrated to give a pink oil. The oil was partitioned between EtOAc and 0.5 M NaOH and the layers were separated. The organic layer was extracted with 0.5 M NaOH (2×). The combined aqueous layers were extracted with EtOAc, acidified with 1.0 N HCl to give a cloudy mixture, and then extracted with EtOAc (3×). The organic layers following acidification were combined, washed with brine, dried over sodium sulfate, filtered and concentrated to give the desired product (0.130 g) as a clear, yellow residue. MS (ESI) m/z: 272.0 (M+H)+.

Provenance & Evidence