Sodium Hydroxide → 2-Amino-4-(phenyltellanyl)butanoic acid

HRID 2058116Notes

Reaction equation

HRID 2058116 reaction equation
[C:1]1([Te:7][CH2:8][CH2:9][CH:10]2[NH:14]C(=O)N[C:11]2=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:17].[Na+]>>[NH2:14][CH:10]([CH2:9][CH2:8][Te:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:11]([OH:16])=[O:17]

Participants

4

Procedure

Reactor produced 123mTe (65.5 mg, 26.3 mCi) was combined with 188.5 mg of carrier Te powder. This material was stirred in tetrahydrofuran (5 ml) to which was added phenyl magnesium chloride (4 mmole) in the same solvent (2 ml). The mixture was stirred rapidly and refluxed but the reaction did not commence as indicated by the absence of the orange-colored product. After the addition of a small crystal of benzoyl peroxide, reaction began immediately. The orange-colored solution was refluxed 1 minute and the reaction flask flushed with O2 and cooled in an ice bath. After warming to room temperature, the solution was stirred 30 minutes, filtered, and the orange-colored filtrate diluted with benzene to a final volume of 25 ml. Aliquots of this solution were counted. The 123mTe-labeled diphenyl ditelluride contained 9.22 mCi of radioactivity. The benzene solution was diluted to 50 ml with methanol and the 123mTe-labeled diphenyl ditelluride reduced with NaBH4 in the manner described in Example IV. To this mixture was added 208 mg, 1 mmole of 5-(beta-bromo ethyl)hydantoin prepared as in Example XI. The mixture was poured into water and extracted with benzene to remove diphenyl ditelluride and other non-polar material. The aqueous layer was acidified to pH 1-2 with 6 N HCl and extracted thoroughly with ether. The combined organic extracts were washed well with water, dried over anhydrous sodium sulfate and the solvent removed in vacuo to give 2.2 mCi of 123mTe-labeled 5-(beta[phenyl telluro]ethyl)hydantoin. This hydantoin is dissolved in 1 N NaOH (2 ml) and heated in a polytetrafluoroethylene-lined bomb by heating at about 165°-167° C. for one hour. Upon cooling, the solution is extracted with benzene and 1 N HCl is added to adjust the pH to 7-8, to provide 123mTe-labeled DL-alpha-amino-gamma-(phenyl telluro)butyric acid.

Workup

  1. temperatureby heating at about 165°-167° C. for one hour
  2. temperatureUpon cooling
  3. extractionthe solution is extracted with benzene and 1 N HCl
  4. additionis added

Sources & evidence

ORD record
ord-2f38b738f0f84a4a80bfef5d6a1af840
Source dataset
uspto-grants-1980_07
Patent number
US04215045

Reaction notes

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