L-Tyrosine → HCID 54333393, compound

Participants

Reaction Steps

To a stirred solution of tyrosine (10 g) in 4N aq. sodium hydroxide (30 mL) cooled in an ice bath was slowly added allyl chloroformate (6.4 mL) in a period of 20 minutes. Ten minutes after completion of the addition the ice bath was removed and 4N aq. sodium hydroxide (30 mL) and H2O (5mL) were added. After two hours at RT MeOH (60 mL) was added. After an additional two hours the reaction mixture was extracted with Et2O. The aq. mixture was cooled in an ice bath, acidified to pH 2-3 using 36-38% hydrochloric acid and extracted with EtOAc. De organic extract was dried (Na2SO4) and concentrated under reduced pressure to give Alloc-Tyr-OH (38) as an oil (14.5 g, 88%). Rf 0.35 (DCM/MeOH/AcOH, 89/10/1, v/v/v).

Provenance & Evidence