Perchloric Acid → D-Phenylalanine 1,1-dimethylethyl ester

HRID 618311Notes

Reaction equation

HRID 618311 reaction equation
[NH2:1][C@@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl(O)(=O)(=O)=O>C(OC(C)(C)C)(=O)C>[CH3:3][C:4]([O:11][C:10](=[O:12])[C@@H:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[NH2:1])([CH3:9])[CH3:5]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 71567D-Phenylalanine

Product 1

HCID 11085361D-Phenylalanine 1,1-dimethylethyl esterYield 11.1%

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

To a solution of D-phenylalanine (5.5 g, 33 mmol) in 430 mL of t-butyl acetate was added concentrated perchloric acid (2 mL, 33 mmol). After stirring at room temperature, the reaction mixture was filtered and the filter cake washed with copious diethyl ether. The filter cake was suspended in diethyl ether and washed with two portions of 5% citric acid. The acid washes were combined, neutralized with solid NaHCO3 and extracted with two portions of diethyl ether. The combined organic extracts were washed with brine, dried with magnesium sulfate and concentrated to give the title compound (404 mg) as a pale yellow liquid and the structure verified by NMR.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe filter cake washed with copious diethyl ether
  3. washwashed with two portions of 5% citric acid
  4. extractionextracted with two portions of diethyl ether
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-380657b89c01494a9dad0b178a236a09
Source dataset
uspto-grants-1999_09
Patent number
US05952377

Reaction notes

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