(2S)-2-amino-2-phenylpropanoic acid → (S)-2-(Boc-amino)-2-phenylpropanoic acid

HRID 875151Notes

Reaction equation

HRID 875151 reaction equation
[C:1]1([C@:7]([C:10]([OH:12])=[O:11])([CH3:9])[NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].C[NH+](C)C.[C:18]([O:22][C:23](=O)[O:24]C(C)(C)C)([CH3:21])([CH3:20])[CH3:19]>C(#N)C>[C:18]([O:22][C:23]([NH:8][C@@:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([C:10]([OH:12])=[O:11])[CH3:9])=[O:24])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 853461(2S)-2-amino-2-phenylpropanoic acidHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 11446287Trimethylazanium hydroxide

Product 1

HCID 13678038(S)-2-(Boc-amino)-2-phenylpropanoic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 500 mg of 2-phenyl-D-alanine (3.02 mmol) and trimethylammonium hydroxide (aqueous solution 10%, 2.8 mL, 3.02 mmol) in 15 mL of acetonitrile, diterbutylcarbonate (1.047 g, 4.8 mmol) was added and the mixture was stirred at room temperature for 2 days. The solvent was then removed under vacuo, the residue was dissolved in water and washed with diethylether. The aqueous layer was acidified to pH=3-4 with citric acid and the product was extracted with ethyl acetate (3×20 mL). The combined organic phase was washed with water, dried over Na2SO4 and evaporated. The title product was recovered as white solid (630 mg, yield 78%).

Workup

  1. additionwas added
  2. customThe solvent was then removed under vacuo
  3. dissolutionthe residue was dissolved in water
  4. washwashed with diethylether
  5. extractionthe product was extracted with ethyl acetate (3×20 mL)
  6. washThe combined organic phase was washed with water
  7. dry with materialdried over Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-3c0afb4300a946d18ec2bcf1e7e38b26
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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