Sodium Hydroxide → HCID 59752292, compound

HRID 1807989Notes

Reaction equation

HRID 1807989 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:8][C:9]=1[N:10]([C:18]([CH:20]1[CH2:25][CH2:24][CH:23]([CH3:26])[CH2:22][CH2:21]1)=[O:19])[CH:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1)=[O:4].Cl.[NH2:34][OH:35].[OH-].[Na+]>CO>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:8][C:9]=1[N:10]([CH:11]1[CH2:16][CH2:15][C:14](=[N:34][OH:35])[CH2:13][CH2:12]1)[C:18]([CH:20]1[CH2:25][CH2:24][CH:23]([CH3:26])[CH2:22][CH2:21]1)=[O:19])=[O:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 597523053-[(4-Methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 59752292HCID 59752292, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[(4-Methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (67 mg, 0.148 mmol) was dissolved in methanol (1.5 ml) and hydroxylamine hydrochloride salt (62 mg, 0.888 mmol) was added. After stirring for 2 hours at room temperature and 2 hours at reflux, the pH of the solution was adjusted to 8-9 by addition of a 10% sodium hydroxide solution. The resulting solution was then refluxed for 30 minutes and cooled to room temperature. It was then quenched with water (5 ml) and extracted with ethyl acetate (3×5 ml). The combined ethyl acetate layer was washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (0% to 60% EtOAc/Hex) to obtain 49 mg (71%) of 3-[(4-Hydroxyimino-cyclohexyl)-(4-methyl-cyclohexanecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester.

Workup

  1. temperatureat reflux
  2. temperatureThe resulting solution was then refluxed for 30 minutes
  3. temperaturecooled to room temperature
  4. customIt was then quenched with water (5 ml)
  5. extractionextracted with ethyl acetate (3×5 ml)
  6. washThe combined ethyl acetate layer was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography (0% to 60% EtOAc/Hex)

Sources & evidence

ORD record
ord-da229b845cca485aab01f76ebb676241
Source dataset
uspto-grants-2013_01
Patent number
US08357718B2

Reaction notes

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