HCID 68956720, compound → HCID 86628161, compound

HRID 1888370Notes

Reaction equation

HRID 1888370 reaction equation
[C:1]([C:3]1[CH:26]=[CH:25][C:6]([O:7][CH2:8][C@@:9]([OH:24])([CH3:23])[C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[C:15]([CH2:21][OH:22])[CH:14]=2)=[O:11])=[CH:5][C:4]=1[F:27])#[N:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[C:1]([C:3]1[CH:26]=[CH:25][C:6]([O:7][CH2:8][C@@:9]([OH:24])([CH3:23])[C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[C:15]([CH:21]=[O:22])[CH:14]=2)=[O:11])=[CH:5][C:4]=1[F:27])#[N:2]

Participants

4

Reactant 2

HCID 68956720HCID 68956720, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 86628161HCID 86628161, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-3-(4-Cyano-3-fluorophenoxy)-N-(4-cyano-3-hydroxymethylphenyl)-2-hydroxy-2-methylpropionamide (170 mg, 0.460 mmol) and pyridinium chloro-chromate (150 mg, 0.696 mmol) in anhydrous CH2Cl2 (10 ml) were stirred for 1 h 45 min at room temperature. Then the solvent was evaporated and the residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 96:4) to afford (S)-3-(4-Cyano-3-fluorophenoxy)-N-(4-cyano-3-formylphenyl)-2-hydroxy-2-methyl-propionamide.

Workup

  1. customThen the solvent was evaporated
  2. customthe residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 96:4)

Sources & evidence

ORD record
ord-f45f76993e244a8f8fa8fb78faada61e
Source dataset
uspto-grants-2013_08
Patent number
US08501814B2

Reaction notes

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