Sulfamic Acid → HCID 67386112, compound

Participants

Reaction Steps

To a solution of 2-(4-chloro-1-oxo-1,3-dihydro-isoindol-2-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (265 mg, 0.60 mmol) in 1,4-dioxane (35 mL) at 0° C. was added a solution of sulfamic acid (349 mg, 3.59 mmol) in water (4.35 mL. Then a solution of NaClO2 (88 mg, 0.78 mmol) and KH2PO4 (977 mg, 7.18 mmol) in water (8.7 mL) was added via dropping funnel over 15 min. The ice bath was removed and the yellow cloudy reaction mixture was stirred at r.t. for 18 h. The reaction mixture was diluted with water and extracted with EtOAc (2×). The combined organic layers were dried over MgSO4 and concentrated to give 269 mg (98%) of 2-(4-chloro-1-oxo-1,3-dihydro-isoindol-2-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid which was used without further purification.

Provenance & Evidence