Trifluoroacetic acid → HCID 54691722, compound

HRID 2214633Notes

Reaction equation

HRID 2214633 reaction equation
C([O:5][C:6](=[O:28])[CH2:7][O:8][N:9]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[C:10]([C:12]1[CH2:13][N:14]([CH3:19])[C:15](=[O:18])[C:16]=1[OH:17])=[O:11])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][N:9]([C:10]([C:12]2[CH2:13][N:14]([CH3:19])[C:15](=[O:18])[C:16]=2[OH:17])=[O:11])[O:8][CH2:7][C:6]([OH:28])=[O:5])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54698236HCID 54698236, compound

Product 1

HCID 54691722HCID 54691722, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

A solution of [(4-fluorobenzyl)-(4-hydroxy-1-methyl-5-oxo-2,5-dihydro-1H-pyrrole-3-carbonyl)-aminooxy]-acetic acid tert-butyl ester (0.041 g, 0.104 mmol) in dichloromethane (4 ml) was treated with trifluoroacetic acid (1 ml) and the resulting mixture was stirred at 22° C. for 2 h. The solvent was evaporated in vacuo and the residue was recrystallized from a mixture of ethyl acetate and hexane to give 0.027 g (80% yield) of the tittle material as white crystals; mp 147–150° C. 1HNMR 400 MHz (DMSO-d6) δ (ppm): 2.95 (3H, s, NCH3), 4.14 (2H, s, CH2), 4.62 (2H, s, CH2), 4.92 (2H, s, CH2), 7.17 (2H, m, aromatics), 7.36 (2H, m, aromatics), 11.4 (1H, broad s, OH), 13.1 (1H, broad s, OH). HRMS (ES+) calculated for C15H16FN2O6, [M+H]+: 339.099240. found: 339.100624.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-84a8b2a919e34890889efe4ecc2fb3af
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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