HCID 22915464, compound → HCID 22915452, compound

HRID 1377908Notes

Reaction equation

HRID 1377908 reaction equation
C([O:8][NH:9][C:10](=[O:28])[CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH:16]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[F:27][C:24]1[CH:23]=[CH:22][C:21]([C:17]2[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=2)[O:14][CH2:13][CH2:12][CH2:11][C:10]([NH:9][OH:8])=[O:28])=[CH:26][CH:25]=1

Participants

4

Reactant 1

HCID 22915464HCID 22915464, compound

Product 1

HCID 22915452HCID 22915452, compoundYield 25.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution in THF (15 mL) of O-benzyl-4-[3-(4-fluorophenyl)phenoxy]butanohydroxamic acid (0.29 g, 0.77 mmol), prepared as in step 3, was added 10% palladium on carbon (0.107 g) and the mixture was stirred overnight under a positive H2 pressure. Purification by reverse phase high performance liquid chromatography gave 4-[3-(4-fluorophenyl)phenoxy]butanohydroxamic acid (57 mg) as a white solid. 1H NMR (DMSO-d6) δ 1.94 (m, 2H), 2.16 (t, 2H, J=7 Hz), 4.03 (t, 2H, J=6 Hz), 6.92 (dd, 1H, J=2, 8 Hz), 7.16 (m, 1H), 7.20 (d, 1H, J=7 Hz), 7.28 (t, 2H, J=9 Hz), 7.37 (t, 1H, J=8 Hz), 7.71 (dd, 2H, J=5, 8 Hz), 8.71 (s, 1H), 10.42 (s, 1H). MS (DCI/NH3) 307 (M+NH4+, 100), 290 (M+H+, 30). Anal. Calcd for: C16H16FNO3 : C, 66.43; H, 5.57; N, 4.84. Found: C, 66.04; H, 5.48; N, 4.78.

Workup

  1. customPurification by reverse phase high performance liquid chromatography

Sources & evidence

ORD record
ord-83613c860db549f1a99200f9a3484409
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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