Hydroxyamine hydrochloride → HCID 136333674, compound

HRID 2289084Notes

Reaction equation

HRID 2289084 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH:5]=[CH:6][C:7]=1[S:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=O)[CH2:20][CH3:21])=[C:15]([OH:23])[C:14]=1[CH2:24][CH2:25][CH3:26].Cl.[NH2:33][OH:34].C([O-])(=O)C.[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH:5]=[CH:6][C:7]=1[S:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[N:33][OH:34])[CH2:20][CH3:21])=[C:15]([OH:23])[C:14]=1[CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 18701926HCID 18701926, compound

Product 1

HCID 136333674HCID 136333674, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 3-chloro-4-(3-(2-propyl-3-hydroxy-4-propionylphenoxy)propylthio)phenylacetate (Step B; 25.655 grams) in dry methanol (260 mL) was treated with hydroxylamine hydrochloride (3.833 grams). Anhydrous sodium acetate (4.524 grams) was added and the mixture refluxed for 4 hours. The reaction mixture was partitioned between isopropyl acetate and pH 7 buffer. The organic phase was washed once with water and dried over magnesium sulfate, filtered and evaporated to an oil. The title compound was used without further purification.

Workup

  1. temperaturethe mixture refluxed for 4 hours
  2. customThe reaction mixture was partitioned between isopropyl acetate and pH 7 buffer
  3. washThe organic phase was washed once with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to an oil
  7. customThe title compound was used without further purification

Sources & evidence

ORD record
ord-7bd8d921062547f6a7833b23931172da
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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