Trifluoroacetic acid → HCID 11368355, compound

HRID 2112429Notes

Reaction equation

HRID 2112429 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C@H:15]([C:28](=[O:30])[NH2:29])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25](=[O:27])[CH3:26])=[CH:19][CH:18]=1)(C)(C)C>ClCCl>[NH2:14][C@@H:15]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25](=[O:27])[CH3:26])=[CH:19][CH:18]=1)[C:28]([NH2:29])=[O:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57642030HCID 57642030, compound

Product 1

HCID 11368355HCID 11368355, compoundYield 24.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (50 ml) was added to a solution of {(S)-1-carbamoyl-2-[4-(2-oxopropoxy)phenyl]ethyl}carbamic acid tert-butyl ester (2.65 g, 7.88 mmol) in dichloromethane (50 ml). The reaction mixture was stirred for 1 h at room temperature. The solvent was removed in vacuo. The residue was dissolved in dichloromethane (50 ml) and the solvent was removed in vacuo. The latter procedure was repeated once. The crude product was purified by C-18 reversed phase chromatography on a HPLC, using a gradient of 13-33% acetonitrile in water in a buffer of trifluoroacetic acid (0.1%) to give 460 mg of (S)-2-amino-3-[4-(2-oxopropoxy)phenyl]propionamide.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (50 ml)
  3. customthe solvent was removed in vacuo
  4. customThe crude product was purified by C-18

Sources & evidence

ORD record
ord-e798ca9843ea4b669a85b0d01be00ea9
Source dataset
uspto-grants-2009_04
Patent number
US07524813B2

Reaction notes

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