O-Benzylhydroxylamine → 2-(Benzyloxyaminomethyl)-4-methylpentanoic acid

HRID 965162Notes

Reaction equation

HRID 965162 reaction equation
[CH3:1][CH:2]([CH3:9])[CH2:3][C:4](=[CH2:8])[C:5]([OH:7])=[O:6].[CH2:10]([O:17][NH2:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([O:17][NH:18][CH2:8][CH:4]([CH2:3][CH:2]([CH3:9])[CH3:1])[C:5]([OH:7])=[O:6])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 102313O-BenzylhydroxylamineHCID 1686594-Methyl-2-methylene valeric acid

Product 1

HCID 193675172-(Benzyloxyaminomethyl)-4-methylpentanoic acid

Procedure

A solution of 4-methyl-2-methylenepentanoic acid (3.5 g) and O-benzylhydroxylamine were heated at 120° for 8 h. The reaction mixture was then partitioned between 50 mL of 1.0N NaOH and 50 mL of diethyl ether. The aqueous portion was separated, acidified to pH 3 with 10% HCl and washed with 50 mL of ether. Ion exchange chromatography (Dowex-50W) eluting with 20% pyridine/water gave 2-(benzyloxyaminomethyl)-4-methylpentanoic acid.

Workup

  1. customThe reaction mixture was then partitioned between 50 mL of 1.0N NaOH and 50 mL of diethyl ether
  2. customThe aqueous portion was separated
  3. washwashed with 50 mL of ether
  4. washIon exchange chromatography (Dowex-50W) eluting with 20% pyridine/water

Sources & evidence

ORD record
ord-b8173411a4154445939911dfa7be7f37
Source dataset
uspto-grants-1998_06
Patent number
US05773428

Reaction notes

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