Hydroxylamine → tert-butyl N-{4-[amino(hydroxyimino)methyl]-2-ethylbenzyl}-N-methylglycinate

HRID 2410556Notes

Reaction equation

HRID 2410556 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]([CH3:17])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[C:5]([CH2:20][CH3:21])[CH:4]=1)#[N:2].[NH2:22][OH:23]>C(O)C>[NH2:2][C:1](=[N:22][OH:23])[C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]([CH3:17])[CH2:9][C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[C:5]([CH2:20][CH3:21])[CH:4]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 66678155tert-butyl N-(4-cyano-2-ethylbenzyl)-N-methylglycinate

Product 1

HCID 76685341tert-butyl N-{4-[amino(hydroxyimino)methyl]-2-ethylbenzyl}-N-methylglycinateYield 103.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl N-(4-cyano-2-ethylbenzyl)-N-methylglycinate (570 mg, 1.98 mmol) and 50% aqueous hydroxylamine (0.6 mL, 10 mmol) in ethanol (10 mL) was heated at 80° C. for 18 hours. The solvent was evaporated in vacuo. The residue was partitioned between DCM and water. The organic phase was passed through a hydrophobic frit and evaporated in vacuo to afford the title compound (658 mg, quantitative). 1H NMR (CDCl3, 400 MHz) δ 7.46 (1H, s), 7.39 (2H, s), 4.85 (2H, br s), 3.73 (2H, s), 3.16 (2H, s), 2.73 (2H, q, J=7.6 Hz), 2.37 (3H, s), 1.47 (9H, s), 1.25-1.19 (3H, m).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customThe residue was partitioned between DCM and water
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-d8c2805302a949bab89569e937f54d61
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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