Hydroxyamine hydrochloride → HCID 22907079, compound

HRID 264294Notes

Reaction equation

HRID 264294 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:13]([CH2:18][CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])[C:14](OC)=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C[O-].[Na+].[Na].Cl.[NH2:36][OH:37]>>[OH:37][NH:36][C:14](=[O:15])[CH:13]([N:12]([S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:18][CH2:19][S:20]([CH3:23])(=[O:22])=[O:21]

Participants

5

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 22907181HCID 22907181, compound

Product 1

HCID 22907079HCID 22907079, compound

Procedure

A solution of methyl 2-[[4-methoxybenzenesulfonyl](benzyl)amino]-4-(methylsulfonyl)butyrate (900 mg, 2.0 mmol), sodium methoxide previously generated from sodium metal spheres (100.0 mg, 4.5 mmol), and hydroxylamine hydrochloride (280.0 mg, 4.0 mmol) is refluxed for 2 days. The mixture is cooled to room temperature, concentrated in vacuo, diluted with water, acidified with citric acid, and extracted with ethyl acetate. The combined organic extracts are dried (MgSO4) and the solvent is evaporated. The product is purified by silica gel chromatography (ethyl acetate) to give N-hydroxy-2-[[4-methoxybenzenesulfonyl](benzyl)amino]-4-(methylsulfonyl)butyramide, [M+1]=157.

Workup

  1. temperatureis refluxed for 2 days
  2. concentrationconcentrated in vacuo
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic extracts are dried (MgSO4)
  6. customthe solvent is evaporated
  7. customThe product is purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-edf3804fc9804224ab0fea6a35025e01
Source dataset
uspto-grants-1997_07
Patent number
US05646167

Reaction notes

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