Sodium Carbonate → HCID 22876609, compound

Participants

Reaction Steps

A solution of 10 g (20.4 mmol) of (S)-N'-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-ylacetyl)-8-oxo-10, 11,12,12a-tetrahydro-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine-1-carboxylic acid hydrazide in 90 g of polyphosphoric acid was stirred at 100° for 1.5 hours. After cooling to room temperature the mixture was poured into 300 ml of ice-water while stirring well, whereupon solid sodium carbonate was added to pH=8. Extraction with methylene chloride and chromatography (silica gel, methylene chloride/methanol 20:1) yielded 7.5 g (78%) of (S)-2-[5-(8-oxo-10,11,12,12a-tetrahydro-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepin-1-yl)-1,3,4-oxadiazol-2-ylmethyl ]-2.3-dihydro-1H-isoindole-1,3-dione as a colourless powder of m.p. >250.

Provenance & Evidence