Hydroxyamine hydrochloride → N-hydroxy-2-[[4-methoxybenzenesulfonyl](benzyl)amino]propionamide

HRID 742029Notes

Reaction equation

HRID 742029 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:13]([CH3:18])[C:14](OC)=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.Cl.[NH2:27][OH:28].C[O-].[Na+]>CO>[OH:28][NH:27][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])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:18]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 22907154Methyl 2-[[4-methoxybenzenesulfonyl](benzyl)amino]propionate

Product 1

HCID 15296597N-hydroxy-2-[[4-methoxybenzenesulfonyl](benzyl)amino]propionamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-[[4-methoxybenzenesulfonyl](benzyl)amino]propionate (2.1 g, 6.01 mmol) is dissolved in methanol (20.0 mL). To this solution is added hydroxylamine hydrochloride (0.84 g, 12.0 mmol), followed by the addition of sodium methoxide (7.0 mL of a 4.37M solution). The reaction is stirred overnight at room temperature. The reaction is worked up by first removing all the solvent, and partitioning between ethyl acetate/hexane (2/1) and saturated sodium bicarbonate. The aqueous phase is extracted well with ethyl acetate/hexane, the combined organic layers 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]propionamide, m.p. 149°-151° C.

Workup

  1. customby first removing all the solvent
  2. custompartitioning between ethyl acetate/hexane (2/1) and saturated sodium bicarbonate
  3. extractionThe aqueous phase is extracted well with ethyl acetate/hexane
  4. dry with materialthe combined organic layers are dried (MgSO4)
  5. customthe solvent is evaporated
  6. customThe product is purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-00b694a9bfee4a718c81ecbe5f01804f
Source dataset
uspto-grants-1996_09
Patent number
US05552419

Reaction notes

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