HCID 23446817, compound → HCID 23446811, compound

HRID 1841645Notes

Reaction equation

HRID 1841645 reaction equation
C([O:9][N:10]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]#[CH:32])=[C:25]([O:33][CH3:34])[CH:24]=1)[C:11](=[O:20])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)(=O)C1C=CC=CC=1>[NH4+].[OH-].CO>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][C:11]([N:10]([OH:9])[CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]#[CH:32])=[C:25]([O:33][CH3:34])[CH:24]=2)=[O:20])=[CH:18][CH:17]=1

Participants

3

Reactant 1

HCID 23446817HCID 23446817, compound

Product 1

HCID 23446811HCID 23446811, compound

Reagents, catalysts & solvents 1

HCID 21894508Ammonium hydroxide methanolSolvent

Procedure

N-Benzoyloxy-2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide (0.3 g, 0.6 mmol) is dissolved in 2 ml 10% NH4OH/MeOH and stirred at room temperature overnight. The solvent is removed under vacuum and the crude product is purified by flash chromatography (ethyl acetate:hexane, 1:2) to yield 2-(4-chloro-phenyl)-N-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide as a solid.

Workup

  1. customThe solvent is removed under vacuum
  2. customthe crude product is purified by flash chromatography (ethyl acetate:hexane, 1:2)

Sources & evidence

ORD record
ord-438116e094424cc29e618cbe09992cb0
Source dataset
uspto-grants-2004_01
Patent number
US06683211B1

Reaction notes

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