Water → HCID 15516568, compound

Participants

Reaction Steps

To a cold solution of 1.1 g (3.31 mmol) of 4-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-N-methyl-2-thiazolemethanamine (Intermediate 58.3) and 0.7 ml (4.96 mmol) of Et3N in 50 ml CH2Cl2 was added portionwise 1.07 (4.96 mmol) of 4-nitrobenzylbromide. After overnight stirring, another portion (0.35 g; 1.65 mmol) of 4-nitrobenzylbromide was added. Twenty four hours later, the reaction mixture was poured into 100 ml of cold water and diluted with 50 ml CH2Cl2. The organic layer was decanted, washed with brine, dried over MgSO4 and filtered. The solvent was eliminated under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (1/1) as eluent. The pure fractions were collected and concentrated to yield 0.98 g (63%) of a yellow solid. Melting point: 111.4-11.7° C.

Provenance & Evidence