HCID 22915476, compound → HCID 22915492, compound

HRID 1377924Notes

Reaction equation

HRID 1377924 reaction equation
C([O:5][NH:6][C:7](=[O:26])[CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)(C)(C)C>FC(F)(F)C(O)=O>[F:25][C:22]1[CH:21]=[CH:20][C:19]([C:16]2[CH:17]=[CH:18][C:13]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]([NH:6][OH:5])=[O:26])=[CH:14][CH:15]=2)=[CH:24][CH:23]=1

Participants

3

Reactant 1

HCID 22915476HCID 22915476, compound

Product 1

HCID 22915492HCID 22915492, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution in trifluoroacetic acid of O-tert-butyl 5-[4-(4-fluorophenyl)phenoxy]pentanohydroxamic acid (0.41 g, 1.1 mmol) was stirred overnight. The reaction mixture was concentrated in vacuo and the residue was suspended in acetonitrile and stirred for 30 minutes. The solid was filtered and dried in vacuo to give 5-[4-(4-fluorophenyl)phenoxy]pentanohydroxamic acid (128 mg) as a white solid. mp 160°-162° C. 1H NMR (DMSO-d6) δ 10.378 (s, 1H), 8.69 (s, 1H), 7.66-7.63 (m, 2H), 7.57-7.55 (d, 2H, J=8.8 Hz), 7.27-7.21 (t, 2H, J=8.8 Hz), 7.02-6.99 (d, 2H, J=8.8 Hz), 4.02-3.98 (t, 2H, J=5.9 Hz), 2.04-2.00 (t, 2H, J=7 Hz), 1.68-1.66 (m, 4H). 13C NMR (DMSO-d6) δ 21.76, 28.15, 31.87, 7.11, 114.85, 115.38, 115.66, 118.34, 127.66, 127.94, 128.03, 131.04, 136.20, 136.33, 158.18, 159.76, 162.98, 168.87. MS (DCI/NH3) 304 (M+H)+, 321 (M+NH4)+. Anal. Calcd for C17H18NO3F: C, 67.31; H, 5.98; N, 4.61. Found: C, 7.19; H, 6.03; N, 4.40.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. filtrationThe solid was filtered
  3. customdried in vacuo

Sources & evidence

ORD record
ord-b9694936a84647d6b813f1fb9361dc22
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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