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

HRID 1600428Notes

Reaction equation

HRID 1600428 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-9e2a651c8f1b4fbcb78a07f7492df0f3
Source dataset
uspto-grants-1998_04
Patent number
US05744631

Reaction notes

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