Hydrogen iodide → HCID 59238168, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 13 (22.4 g, 47 mmol) in HOAc (448 mL) was added HI (268 mL). The mixture was heated to reflux at 120° C. overnight. The reaction mixture was evaporated and its pH was adjusted to 6-7 with potassium carbonate and NaHCO3. Then 50 mL of tetrahydrofuran was added. To the mixture was added FmocCl (15.68 g, 61 mmol) and stirred at room temperature for 5 h. Then the reaction mixture was extracted with ethyl acetate and washed with water 3 times. The organic layer was dried over sodium sulfate, filtered and evaporated to dryness. Purification by chromatography (eluant:methylene chloride to methylene chloride/MeOH/HAc 8/1/0.1) gave 10.3 g of crude 5-(3-carboxymethyl-4-oxo-3,4-dihydro-quinazolin-6-yl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid 9H-fluoren-9-ylmethyl ester which was further purified by preparative HPLC to give 2.7 g of pure 5-(3-carboxymethyl-4-oxo-3,4-dihydro-quinazolin-6-yl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid 9H-fluoren-9-ylmethyl ester (11% yield in 2 steps).

Provenance & Evidence