Trifluoroacetic acid methylene chloride → HCID 9839147, compound

HRID 1377926Notes

Reaction equation

HRID 1377926 reaction equation
C([O:5][NH:6][C:7](=[O:26])[CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][C:24]#[N:25])[CH:18]=2)=[CH:13][CH:12]=1)(C)(C)C.FC(F)(F)C(O)=O.ClCCl>>[C:24]([CH2:23][C:19]1[CH:18]=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][C:7]([NH:6][OH:5])=[O:26])=[CH:12][CH:13]=2)[CH:22]=[CH:21][CH:20]=1)#[N:25]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 22915462HCID 22915462, compound

Product 1

HCID 9839147HCID 9839147, compoundYield 45%

Procedure

A solution of O-tert-butyl 3-[4-(3-cyanomethylphenyl)phenoxy]propanohydroxamic acid (0.043 g, 0.12 mmol) in 1:1 trifluoroacetic acid-dichloromethane was stirred overnight at ambient temperature. The reaction mixture was filtered, concentrated in vacuo, and azeotroped with dichloromethane and dichloromethane-ethyl ether. Chromatography on silica gel (40:1, then 20:1 dichloromethane-methanol, both containing 0.25% acetic acid) gave 3-[4-(3-cyanomethylphenyl)phenoxy]propanohydroxamic acid (16 mg, 44%). 1H NMR (DMSO-d6) δ 2.45 (t, 2H, J=6.0 Hz), 4.08 (s, 2H), 4.23 (t, 2H, J=6.0 Hz), 7.02 (d, 2H, J=8.8 Hz), 7.29 (d, 1H, J=7.5 Hz), 7.46 (t, 1H, J=8.0 Hz), 7.57 (d, 1H, J=6 Hz), 7.58 (s, 1H), 7.60 (d, 2H, J=8.8 Hz); 8.84 (br s, 1H), 10.53 (br s, 1H). IR (microscope) 3245 (br), 2924 (m), 2251 (w), 1643 (s), 1608 (s), 1518 (s), i483 (m), 1244 (s), 784 (m) cm-1. MS (DCI/NH3) 314 (M+NH4)+. Anal. Calcd for C17H16N2O3 ·0.70 H2O·0.20 tBuOH: C, 66.04; H, 6.04; N, 8.65. Found: C, 65.93; H, 5.64; N, 8.30.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customazeotroped with dichloromethane and dichloromethane-ethyl ether

Sources & evidence

ORD record
ord-988dc00564f640b4bd66b1196be48441
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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