Reacción #362830

ord-6c6cf981a47b4307bfcdb6d7c3a31605

Ecuación de reacción

CC(C)(C)OC(=O)N[C@@H](Cc1ccc(OCCCl)cc1)C(=O)O
(S)-N-tert-butoxycarbonyl-4-O-(2-chloroethyl)tyrosine
Cl.N[C@@H](Cc1ccc(OCCCl)cc1)C(=O)O
(S)-4-O-(2-chloroethyl)tyrosine hydrochloride
Rendimiento 77.6%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroare placed in a round-bottomed flask
  2. 2
    Concentraciónthe mixture is concentrated to dryness under reduced pressure
  3. 3
    workup.STIRRINGthis solution is then stirred
  4. 4
    Filtraciónfiltered
  5. 5
    LavadoThe resulting solid is washed with 2 times 25 ml of ether
  6. 6
    Otrodried under reduced pressure in order

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06352839B1uspto-grants-2002_03