Ethyl bromoacetate → Boc-L-Trp(CH2COOEt)-OBzl

Participants

Reaction Steps

To a solution of Boc-L-Trp-OBzl (5.00 g), tetra-n-butylammonium sulfate (43 mg) and NaOH (sodium hydroxide) (1.27 g) in methylene chloride (100 ml) was added a solution of ethyl bromoacetate (5.29 g) in methylene chloride (50 ml) in an ice-bath cooling. After being stirred at room temperature for 2 days, the mixture was washed with 5% aqueous potassium hydrogen sulfate solution, 1M aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated in vacuo to afford Boc-L-Trp(CH2COOEt)-OBzl (6.10 g) as an oil.

Provenance & Evidence