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

HRID 44650Notes

Reaction equation

HRID 44650 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-fb4951d7af0d4849878154799b7a4aa2
Source dataset
uspto-grants-2013_09
Patent number
US08541429B2

Reaction notes

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