Trifluoroacetic acid → HCID 69939868, compound

HRID 1058962Notes

Reaction equation

HRID 1058962 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:32])[CH2:11][NH:12][C:13](=[O:31])[C@@H:14]([NH:22][CH2:23]C(OC(C)(C)C)=O)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>ClCCl>[CH3:8][O:9][C:10](=[O:32])[CH2:11][NH:12][C:13](=[O:31])[C@@H:14]([NH:22][CH3:23])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69938689HCID 69938689, compound

Product 1

HCID 69939868HCID 69939868, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 mL) was added to a solution of (S)-N-(2-{N-[(1,1-dimethylethoxy)carbonyl]methylamino}-1-oxo-3-phenylpropyl)glycine methyl ester (Description 32, 2.28 g, 6.5 mmol) in dichloromethane (50 mL) and the mixture was stirred at room temperature for 3.5 h. The solvent was evaporated under reduced pressure, then toluene was added and evaporated under reduced pressure. Aqueous sodium carbonate (10%, 100 mL) was added and the mixture was extracted with dichloromethane (2×100 mL). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2/MeOH (95:5), to give the title compound as a colorless oil (1.59 g, 98%). 1H NMR (250 MHz, CDCl3) δ7.71 (1H, br s), 7.61-7.21 (5H, m), 4.15 (1H, dd, J 18.3, 6.1 Hz), 4.02 (1H, dd, J 18.3, 5.5 Hz), 3.76 (3H, s), 3.25 (2H, m), 2.69 (1H, dd, J 14.7, 10.9 Hz), 2.31 (3H, s), and 1.30 (1H, br s). m/z (ES+) 251 (M+1).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additiontoluene was added
  3. customevaporated under reduced pressure
  4. additionAqueous sodium carbonate (10%, 100 mL) was added
  5. extractionthe mixture was extracted with dichloromethane (2×100 mL)
  6. dry with materialThe combined organic fractions were dried (MgSO4)
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by flash column chromatography on silica gel
  9. washeluting with CH2Cl2/MeOH (95:5)

Sources & evidence

ORD record
ord-4f938ef44fc940278a4918cfa9ce6276
Source dataset
uspto-grants-2003_02
Patent number
US06518273B1

Reaction notes

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