Citric Acid → HCID 131730353, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(2-tert-butoxycarbonylamino-ethoxy)-3,5-bis-(tert-butyl-dimethyl-silyloxymethyl)-benzene (270 mg) in tetrahydrofurane (5 mL) was added iodomethane (70 μL) and the reaction mixture was cooled (0° C.). To the cooled solution, sodium hydride was added (68 mg). After 1 hour, the temperature was allowed to warm up to room temperature. After 16 hours, a mixture of THF and water 1:1 (2 mL) was slightly added, then citric acid until pH=2. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo to a residue. The residue was purified by silica gel chromatography (Merck SuperVarioFlash 25 g column, Si60 15-40 μm), using gradient elution with a mixture of heptane (A)/ethyl acetate (B), (gradient: 100% A down to 85% A: 15% B) to give 1-(2-(tert-butoxycarbonyl)-methylamino-ethoxy)-3,5-bis-(tert-butyl-dimethyl-silyloxy methyl)-benzene (220 mg): LC/MS (Method A2): ES: m/z 562 (M+Na)+; m/z 308 (M+H−C5H8O2−OSiC6H16)+; RT=1.50 min

Provenance & Evidence