Triethylamine → HCID 19048401, compound

Participants

Reaction Steps

To a stirred solution of N,N'-bis[2,3-bis(acetyloxy)propyl]-2,4,6-triiodo-5-[[(tetrahydro-2-furanyl]carbonyl]amino]-1,3-benzenedicarboxamide (0.25 g, 0.26 mmol) (the title compound of Example 19) in dry CH2Cl2 (5 mL) was added triethyl amine (0.01 mL). The solution was cooled to 0°-5°, and to this was added dropwise a solution of dimethylboron bromide in CH2Cl2 (0.12 g, 0.5 mL/2 mMol solution in CH2CL2). After stirring the mixture at 0°-5° for 6-8 hours, the mixture was added to a vigorously stirred solution of aqueous saturated sodium bicarbonate (5 mL). After stirring for 5 minutes, ethyl acetate (50 mL) and water (10 mL) were added. The organic layer was separated, washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to yield the omega-bromo-alpha-hydroxypentanoyl anilide as an off-white fluffy solid (260 mg).

Provenance & Evidence