Perchloric Acid → Tert-butyl 3-amino-3-(4-hydroxyphenyl)propanoate

Participants

Reaction Conditions

Reaction Steps

1.00 g (5.52 mmol) commercial 3-amino-3-(4-hydroxy-phenyl)-propionic acid were suspended in 20 ml tert-butyl acetate and the mixture cooled to 15° C. 0.90 ml (11.10 mmol) perchloric acid were slowly added and the mixture stirred at 20° C. for 1.5 hours. The solution was extracted with saturated sodium hydrogen carbonate solution. The aqueous layer was brought to pH=8 with sodium carbonate and extracted with ethyl acetate. The organic parts were combined, dried over sodium sulfate and concentrated to yield 1.0 g (60%) racemic 3-amino-3-(4-hydroxy-phenyl)-propionic acid tert-butyl ester. This was separated into the enantiomers by HPLC:

Provenance & Evidence