Trifluoroacetic acid → (S)-N-ethylalanine methyl ester

HRID 69610Notes

Reaction equation

HRID 69610 reaction equation
C(OC([N:8]([CH2:15][CH3:16])[C@@H:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH2:15]([NH:8][C@@H:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])[CH3:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58324365(S)-methyl 2-(tert-butoxycarbonyl(ethyl)amino)propanoate

Product 1

HCID 43230256(S)-N-ethylalanine methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-methyl 2-(tert-butoxycarbonyl(ethyl)amino)propanoate (4.40 g, 19.0 mmol) was dissolved in dichloromethane and treated with TFA (10 mL). The reaction mixture was stirred for 2 h at room temperature and concentrated in vacuo. The residue was diluted with brine and NaOH (aq. 50%) was added dropwise until pH=12.5. This was extracted with EtOAc (3×30 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as an opaque liquid (1.85 g, 74%). [M+H] calc'd for C6H13NO2, 132; found, 132.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with brine and NaOH (aq. 50%)
  3. additionwas added dropwise until pH=12.5
  4. extractionThis was extracted with EtOAc (3×30 mL)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d32631dd4ac340e9b5a8a46525fb3c03
Source dataset
uspto-grants-2014_09
Patent number
US08822470B2

Reaction notes

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