Hydroxylamine → tert-butyl N-{5-[amino(hydroxyimino)methyl]-2-fluorobenzyl}-N-methylglycinate

HRID 219879Notes

Reaction equation

HRID 219879 reaction equation
[NH2:1][OH:2].[C:3]([C:5]1[CH:6]=[CH:7][C:8]([F:22])=[C:9]([CH:21]=1)[CH2:10][N:11]([CH3:20])[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])#[N:4]>CCO>[NH2:4][C:3](=[N:1][OH:2])[C:5]1[CH:6]=[CH:7][C:8]([F:22])=[C:9]([CH:21]=1)[CH2:10][N:11]([CH3:20])[CH2:12][C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 67529926tert-butyl N-(5-cyano-2-fluorobenzyl)-N-methylglycinate

Product 1

HCID 72307469tert-butyl N-{5-[amino(hydroxyimino)methyl]-2-fluorobenzyl}-N-methylglycinate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine (50% in water) (539.42 μL; 8.98 mmol; 5 eq.) was added to a solution of tert-butyl N-(5-cyano-2-fluorobenzyl)-N-methylglycinate, obtained in step 1 (500 mg; 1.80 mmol; 1 eq.) in EtOH (20 mL) and the resulting mixture was stirred at RT for 24 hours. Solvent was evaporated in vacuo and the resulting oily residue was freeze-dried to afford the title compound as a colourless oil (602 mg; quantitative). 1H NMR (DMSO-d6, 300 MHz) δ 9.61 (br s, 1H), 7.73 (dd, J=7.3, 2.3 Hz, 1H), 7.62-7.56 (m, 1H), 7.20-7.12 (m, 1H), 5.81 (s, 2H), 3.71 (s, 2H), 3.20 (s, 2H), 2.28 (s, 3H), 1.43 (s, 9H). LC/MS (Method B): 310.1 (M−H)−, 312.2 (M+H)+.

Workup

  1. customSolvent was evaporated in vacuo
  2. customthe resulting oily residue was freeze-dried

Sources & evidence

ORD record
ord-cc14bb4fe4b34588b18fdb90dcd6f92d
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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