Trifluoroacetic acid → HCID 54698234, compound

HRID 2214628Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 4-{[(4-hydroxy-1-methyl-5-oxo-2,5-dihydro-1H-pyrrole-3-carbonyl)-methoxyamino]-methyl}-benzoic acid tert-butyl ester (0.062 g, 0.16 mmol) in dichloromethane (3 ml) was treated with trifluoroacetic acid (0.6 ml) and stirred at 25° C. for 2 h. The solvent was then evaporated in vacuo and the residue was triturated with acetonitrile to give 0.041 g (80% yield) of the title material as a white solid; mp 196–197° C. 1HNMR 400 MHz (DMSO-d6) δ (ppm): 2.97 (3H, s, NCH3), 3.73 (3H, s, OCH3), 4.19 (2H, s, NCH2), 4.96 (2H, s, NCH2), 7.42 (2H, d, J=8.3 Hz, aromatics), 7.91 (2H, d, J=8.3 Hz, aromatics), 11.4 (1H, broad s, OH), 12.9 (1H, broad s, OH). Anal. calcd for C15H16N2O6.H2O: C, 53.25; H, 5.36; N, 8.28. Found: C, 53.59; H, 4.79; N, 8.19.

Workup

customThe solvent was then evaporated in vacuo
customthe residue was triturated with acetonitrile

Sources & evidence

ORD record: ord-54774d7ad9bd4b0cbf3bd88a2d6a44d9
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109186B2

Reaction notes

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