Reaction #362830

Reaction equation

(S)-N-tert-butoxycarbonyl-4-O-(2-chloroethyl)tyrosine

→

(S)-4-O-(2-chloroethyl)tyrosine hydrochloride

Yield 77.6%

Solvents

dioxane

Conditions

Workup

1. 1
   Otherare placed in a round-bottomed flask
2. 2
   Concentrationthe mixture is concentrated to dryness under reduced pressure
3. 3
   workup.STIRRINGthis solution is then stirred
4. 4
   Filtrationfiltered
5. 5
   WashThe resulting solid is washed with 2 times 25 ml of ether
6. 6
   Otherdried under reduced pressure in order

Procedure

5 g of (S)-N-tert-butoxycarbonyl-4-O-(2-chloroethyl)tyrosine, dissolved in 50 ml of hydrochloric dioxane, are placed in a round-bottomed flask. After having been stirred for 28 h, the mixture is concentrated to dryness under reduced pressure. The resulting residue is taken up in 50 ml of ether and this solution is then stirred and filtered. The resulting solid is washed with 2 times 25 ml of ether and then dried under reduced pressure in order to yield 1.58 g of (S)-4-O-(2-chloroethyl)tyrosine hydrochloride in the form of a white solid which melts at 260° C.

Source