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

HRID 2404307Notes

Reaction equation

HRID 2404307 reaction equation
[NH2:1][OH:2].[C:3]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][N:10]([CH3:19])[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:7][CH:6]=1)#[N:4]>CCO.O>[NH2:4][C:3](=[N:1][OH:2])[C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]([CH3:19])[CH2:11][C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 66678135tert-butyl N-(4-cyanobenzyl)-N-methylglycinate

Product 1

HCID 76685327tert-butyl N-{4-[amino(hydroxyimino)methyl]benzyl}-N-methylglycinateYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A 50% aqueous solution of hydroxylamine (13.25 mL, 225 mmol) was added at once into a solution of tert-butyl N-(4-cyanobenzyl)-N-methylglycinate (11.70 g, 45 mmol) in EtOH (75 mL). The reaction mixture was stirred at RT overnight. The solvents were removed under reduced pressure to give a white solid. The solid was suspended in water (200 mL) and stirred for 20 minutes, then filtered off, washed with water and dried to give the title compound as a white powder (12.54 g, 95%). 1H NMR (DMSO-d6, 300 MHz) δ 9.58 (s, 1H), 7.62 (d, J=8.3 Hz, 2H), 7.28 (d, J=8.3 Hz, 2H), 5.78 (s, 2H), 3.62 (s, 2H), 3.15 (s, 2H), 2.24 (s, 3H), 1.42 (s, 9H). LC/MS (Method B): 294.0 (M+H)+.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customto give a white solid
  3. stirringstirred for 20 minutes
  4. filtrationfiltered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-06a2d645c54049e78e524ad12a4afac1
Source dataset
uspto-grants-2014_08
Patent number
US08802704B2

Reaction notes

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