HCID 67526105, compound → HCID 86612739, compound

HRID 133770Notes

Reaction equation

HRID 133770 reaction equation
[C:1]([C:3]1[CH:27]=[CH:26][C:6]([O:7][CH2:8][C:9]([OH:25])([CH3:24])[C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([CH2:22][OH:23])[CH:14]=2)=[O:11])=[CH:5][C:4]=1[F:28])#[N:2]>ClCCl.[O-2].[Mn+4].[O-2]>[C:1]([C:3]1[CH:27]=[CH:26][C:6]([O:7][CH2:8][C:9]([OH:25])([CH3:24])[C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([CH:22]=[O:23])[CH:14]=2)=[O:11])=[CH:5][C:4]=1[F:28])#[N:2]

Participants

4

Reactant 1

HCID 67526105HCID 67526105, compound

Product 1

HCID 86612739HCID 86612739, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

3-(4-Cyano-3-fluorophenoxy)-2-hydroxy-N-(3-hydroxymethyl-4-nitrophenyl)-2-methylpropionamide (0.2 g, 0.51 mmol) was dissolved in dichloromethane (10 ml) and manganese(IV) oxide (0.4 g, 4.6 mmol) was added. The mixture was stirred at room temperature for 48 hours. The solid oxidant was removed by filtration and the solvent was evaporated. The crude product was purified by flash chromatography (dichloromethane-3% methanol). 1H NMR (400 MHz, DMSO-d6): 1.45 (3H, s), 4.13 (1H, d, J=10.0 Hz), 4.38 (1H, d, J=10.0 Hz), 6.32 (1H, s), 6.94-6.97 (1H, m), 7.16-7.20 (1H, m), 7.77-7.82 (1H, m), 8.18-8.24 (2H, m), 8.36 (1H, d, J=2.1 Hz), 10.28 (1H, s), 10.55 (1H, s).

Workup

  1. customThe solid oxidant was removed by filtration
  2. customthe solvent was evaporated
  3. customThe crude product was purified by flash chromatography (dichloromethane-3% methanol)

Sources & evidence

ORD record
ord-3f26d7cf33244c2d96859e900a3c88b7
Source dataset
uspto-grants-2008_06
Patent number
US07390923B2

Reaction notes

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