Sodium Hydroxide → N-[3-((hydroxyimino)methyl)benzyl]succinamic acid tert-butyl ester

HRID 2112434Notes

Reaction equation

HRID 2112434 reaction equation
[OH-:1].[Na+].[C:3]([O:7][C:8](=[O:23])[CH2:9][CH2:10][C:11]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=O)[CH:16]=1)=[O:12])([CH3:6])([CH3:5])[CH3:4].Cl.[NH2:25]O.S([O-])(O)(=O)=O.[Na+]>C(O)C.O>[C:3]([O:7][C:8](=[O:23])[CH2:9][CH2:10][C:11]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=[N:25][OH:1])[CH:16]=1)=[O:12])([CH3:6])([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 516919Sodium BisulfateHCID 57642047N-(3-formylbenzyl)succinamic acid tert-butyl ester

Product 1

HCID 76573399N-[3-((hydroxyimino)methyl)benzyl]succinamic acid tert-butyl esterYield 76%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A 3.2 M aqueous solution of sodium hydroxide (0.5 ml, 1.60 mmol) was added to a solution of N-(3-formylbenzyl)succinamic acid tert-butyl ester (312 mg, 1.07 mmol) and hydroxylamine hydrochloride (89 mg, 1.29 mmol) in ethanol (2.5 ml) and water (0.5 ml). The reaction mixture was stirred at room temperature for 3 days. A 10% aqueous solution of sodium hydrogensulphate (20 ml) and water (50 ml) were added. The mixture was extracted with ethyl acetate (3×50 ml). The combined organic layers were dried over magnesium sulphate. The solvent was removed in vacuo to give 249 mg of crude N-[3-((hydroxyimino)methyl)benzyl]succinamic acid tert-butyl ester, which was used without further purification in the next step.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×50 ml)
  2. dry with materialThe combined organic layers were dried over magnesium sulphate
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-01d2ac7727da40bd8a5691c749c5bc46
Source dataset
uspto-grants-2009_04
Patent number
US07524813B2

Reaction notes

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