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

HRID 275648Notes

Reaction equation

HRID 275648 reaction equation
C(OC([NH:8][C@H:9]([C:21]([OH:23])=[O:22])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][Cl:20])=[CH:13][CH:12]=1)=O)(C)(C)C>O1CCOCC1>[ClH:20].[Cl:20][CH2:19][CH2:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][C@@H:9]([C:21]([OH:23])=[O:22])[NH2:8])=[CH:16][CH:15]=1

Participants

3

Reactant 1

HCID 22950710(S)-N-tert-butoxycarbonyl-4-O-(2-chloroethyl)tyrosine

Product 1

HCID 22950707(S)-4-O-(2-chloroethyl)tyrosine hydrochlorideYield 77.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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.

Workup

  1. customare placed in a round-bottomed flask
  2. concentrationthe mixture is concentrated to dryness under reduced pressure
  3. stirringthis solution is then stirred
  4. filtrationfiltered
  5. washThe resulting solid is washed with 2 times 25 ml of ether
  6. customdried under reduced pressure in order

Sources & evidence

ORD record
ord-6c6cf981a47b4307bfcdb6d7c3a31605
Source dataset
uspto-grants-2002_03
Patent number
US06352839B1

Reaction notes

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