Trifluoroacetic acid → HCID 9837913, compound

HRID 988016Notes

Reaction equation

HRID 988016 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:29])[CH2:14][CH:15]([NH:20][C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16](=[O:19])[CH2:17][F:18])(C)(C)C>C(Cl)Cl>[C:21]([NH:20][CH:15]([C:16](=[O:19])[CH2:17][F:18])[CH2:14][C:13]([OH:29])=[O:12])(=[O:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86585878HCID 86585878, compound

Product 1

HCID 9837913HCID 9837913, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic acid (TFA) (10 ml) was added to a stirred ice cold solution of above prepared 3-benzoylamino-5-fluoro-4-oxo-pentanoic acid tert-butyl ester (600 mg, 1.94 mmol) in dry DCM (10 ml). The mixture was stirred at 0° C. for 0.5 h then at r.t. for 0.5 h. The mixture was concentrated under reduced pressure and the residue redissolved in dry DCM. This process was repeated several times in order to remove excess TFA. The resulting gum was triturated with Et2O. Filtration of the resulting suspension yielded the title compound as finely divided white powder (333 mg, 68%): 1H NMR (DMSO) δ 12.6 (1H, br s), 8.8 (1H, br m), 7.85 (2H, m), 7.50 (3H, m), 4.90 (2H, m), 4.80 (1H, m), 2.80 (2H, m); 13C NMR (DMSO) δ 166.97, 133.72, 132.5, 128.70, 127.83, 52.64, 34.58; 19F NMR (DMSO) δ −226.66(m), −230.34(m), −232.24(m); Acc. Mass; Calc. 254.0828, Found 254.0793.

Workup

  1. waitat r.t. for 0.5 h
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionthe residue redissolved in dry DCM
  4. customto remove excess TFA
  5. customThe resulting gum was triturated with Et2O
  6. filtrationFiltration of the resulting suspension

Sources & evidence

ORD record
ord-11599255e9a24cbe9f3139224f5a0b3e
Source dataset
uspto-grants-2003_10
Patent number
US06632962B2

Reaction notes

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