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

HRID 2307897Notes

Reaction equation

HRID 2307897 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-06ba8c9c90e545769ccb3160f21300c9
Source dataset
uspto-grants-2004_12
Patent number
US06833382B2

Reaction notes

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