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

HRID 219886Notes

Reaction equation

HRID 219886 reaction equation
[NH2:1][OH:2].[C:3]([C:5]1[CH:6]=[CH:7][C:8]([F:23])=[C:9]([CH:22]=1)[CH2:10][N:11]([CH3:21])[CH2:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])#[N:4]>CCO>[NH2:4][C:3](=[N:1][OH:2])[C:5]1[CH:6]=[CH:7][C:8]([F:23])=[C:9]([CH:22]=1)[CH2:10][N:11]([CH3:21])[CH2:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 66677998tert-butyl N-(5-cyano-2-fluorobenzyl)-N-methyl-beta-alaninate

Product 1

HCID 72307493tert-butyl N-{5-[amino(hydroxyimino)methyl]-2-fluorobenzyl}-N-methyl-beta-alaninate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine (50% in water) (513.54 μL; 8.55 mmol; 5 eq.) was added to a solution of tert-butyl N-(5-cyano-2-fluorobenzyl)-N-methyl-beta-alaninate, obtained in step 1 (500 mg; 1.71 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 (560 mg; quantitative). 1H NMR (CDCl3) δ 7.74 (dd, J=6.6, 2.2 Hz, 1H), 7.58-7.53 (m, 1H), 7.03 (t, J=9.1 Hz, 1H), 5.10 (s, 2H), 3.59 (s, 2H), 2.69 (t, J=7.0 Hz, 2H), 2.44 (t, J=6.9 Hz, 2H), 2.28 (s, 3H), 1.46 (s, 9H). LC/MS (Method B): 326.2 (M+H)+. HPLC (Method A) Rt 2.18 min (Purity: 86.2%).

Workup

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

Sources & evidence

ORD record
ord-36d9b8fb066e42a28988e87939f9dfe7
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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