Tetrahydrofuran → HCID 68500245, compound

Participants

Reaction Conditions

Reaction Steps

In a 500 mL flask charged with carboxylic acid from step D (12 g, 46.8 mmol) in THF (300 mL) at 0° C. was added carbonyl diimidazole (9.1 g, 56.2 mmol) portionwise. Upon complete addition (10 min.) the ice bath was removed and the reaction stirred for 1 h. At this time the mixture was re-cooled to 0° C. and isopropylamine added dropwise (4.98 g, 84 mmol). The mixture was warmed to rt and the reaction complete within 2 h as indicated by LC-MS. The mixture was concentrated and treated with EtOAc and aq. Na2HCO3. The organic layer was washed with brine; dried over Na2SO4 and concentrated to via rotary evaporation and further dried in vacuo. The crude product was re-crystallized from EtOAc/hexanes to give 11.7 g of final product as a colorless solid (84%): LC-MS (M+H)=298.0.

Provenance & Evidence