Trifluoroacetic acid → (S)-2-amino-N-benzyl-N-(2-hydroxyethyl)butanamide

HRID 249873Notes

Reaction equation

HRID 249873 reaction equation
C(O)(C(F)(F)F)=O.[CH2:8]([N:15]([CH2:29][CH2:30][OH:31])[C:16](=[O:28])[C@@H:17]([NH:20]C(=O)OC(C)(C)C)[CH2:18][CH3:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[NH2:20][C@@H:17]([CH2:18][CH3:19])[C:16]([N:15]([CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:29][CH2:30][OH:31])=[O:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66874668(S)-tert-butyl 1-(benzyl(2-hydroxyethyl)amino)-1-oxobutan-2-ylcarbamate

Product 1

HCID 66874126(S)-2-amino-N-benzyl-N-(2-hydroxyethyl)butanamideYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

TFA(10 mL) was added to (S)-tert-butyl 1-(benzyl(2-hydroxyethyl)amino)-1-oxobutan-2-ylcarbamate (3 g, 8.92 mmol) in CH2Cl2 (50 mL) at 0° C. The mixture was stirred at 0° C. for 1.5 h, followed by solvent removal under reduced pressure. The residue was partitioned between CH2Cl2 (300 mL) and 25% aqueous sodium hydroxide (100 mL). The aqueous fraction was further extracted with CH2Cl2 (2×100 mL), and combined organic fraction was dried (Na2SO4), filtered and concentrated to afford (S)-2-amino-N-benzyl-N-(2-hydroxyethyl)butanamide as a yellow oil (1.84 g, 87%). 1H NMR consistent.

Workup

  1. customfollowed by solvent removal under reduced pressure
  2. customThe residue was partitioned between CH2Cl2 (300 mL) and 25% aqueous sodium hydroxide (100 mL)
  3. extractionThe aqueous fraction was further extracted with CH2Cl2 (2×100 mL)
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-551ff0636d9b408ca6024fa134892363
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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