Trifluoroacetic acid → 5-Fluoro-4-oxo-3-[(S)-2-(2-oxo-2H-pyridin-1-yl)-propionylamino]-pentanoic acid

HRID 602923Notes

Reaction equation

HRID 602923 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:32])[CH2:14][CH:15]([NH:20][C:21](=[O:31])[C@@H:22]([N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]1=[O:30])[CH3:23])[C:16](=[O:19])[CH2:17][F:18])(C)(C)C>ClCCl>[F:18][CH2:17][C:16](=[O:19])[CH:15]([NH:20][C:21](=[O:31])[C@@H:22]([N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]1=[O:30])[CH3:23])[CH2:14][C:13]([OH:32])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 865905065-Fluoro-4-oxo-3-[(S)-2-(2-oxo-2H-pyridin-1-yl)-propionylamino]-pentanoic acid tert-butyl ester

Product 1

HCID 99660225-Fluoro-4-oxo-3-[(S)-2-(2-oxo-2H-pyridin-1-yl)-propionylamino]-pentanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic acid (2 ml) was added to a stirred ice cold solution of 5-Fluoro-4-oxo-3-[(S)-2-(2-oxo-2H-pyridin-1-yl)-propionylamino]-pentanoic acid tert-butyl ester (115 mg, 0.32 mmol) in anhydrous dichloromethane (2 ml). The mixture was stirred at 0° C. for 0.5 h then at room temperature for 0.5 h. The mixture was concentrated under reduced pressure and then the residue was redissolved in dry dichloromethane. This process was repeated several times in order to remove excess trifluoroacetic acid. The gum was lyophilized twice from HPLC grade water to afford the title compound as an off white solid: IR (solid) 1789, 1730, 1654 cm−1; 1H NMR (400 MHz, DMSO) δ 1.4-1.6 (3H, m), 2.5-2.9 (2H, m), 4.2-4.7 (2H, m), 5.0-5.5 (2H, m), 6.2-6.3 (1H, m), 6.3-6.5 (1H, m), 7.3-7.4 (1H, m), 7.6-7.7 (1H, m), 8.4-8.9 (1H, m); 13C NMR (100 MHz, DMSO) δ 17.15, 17.27, 17.61, 17.87, 17.94, 33.50, 33.57, 35.02, 35.23, 35.31, 52.69, 53.08, 53.31, 53.42, 53.47, 53.79, 53.91, 54.49, 54.85, 81.55, 81.92, 83.31, 83.68, 83.95, 84.07, 85.72, 85.84, 105.87, 106.07, 106.19, 119.67, 119.86, 120.26, 137.05, 137.31, 137.36, 137.40, 137.43, 140.60, 140.65, 140.74, 140.85, 162.14, 162.18, 162.28, 162.32, 171.25, 171.48, 171.62, 171.69, 172.55, 172.63, 173.63, 173.67, 174.52, 203.04, 203.18, 203.28, 203.42; MS (FAB +ve, HR) Calculated for C13H16FN2O5 (MH+) 299.1043. found 299.1045.

Workup

  1. waitat room temperature for 0.5 h
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionthe residue was redissolved in dry dichloromethane
  4. customto remove excess trifluoroacetic acid

Sources & evidence

ORD record
ord-9413fc5d8259484baf1df7a805ba0b95
Source dataset
uspto-grants-2011_03
Patent number
US07906650B2

Reaction notes

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