Hydroxylamine → HCID 76685322, compound

HRID 2410563Notes

Reaction equation

HRID 2410563 reaction equation
[C:1]([C:3]1[CH:19]=[C:18]([F:20])[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]([F:21])[CH:4]=1)#[N:2].[NH2:22][OH:23]>C(O)C>[F:21][C:5]1[CH:4]=[C:3]([C:1](=[N:22][OH:23])[NH2:2])[CH:19]=[C:18]([F:20])[C:6]=1[CH2:7][N:8]([CH3:17])[CH2:9][C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 66677503HCID 66677503, compound

Product 1

HCID 76685322HCID 76685322, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 2-((4-cyano-2,6-difluorobenzyl)(methyl)amino)acetate (0.281 g, 0.95 mmol) and 50% aqueous hydroxylamine (0.32 mL) in ethanol (1.3 mL) was heated at 75° C. for 18 hours. The solvent was evaporated in vacuo. The residue was partitioned between EtOAc and water, and then the organic phase was passed through a hydrophobic frit. The solvent was evaporated in vacuo to afford the title compound. 1H NMR (CDCl3, 400 MHz) δ 7.22-7.13 (2H, m), 4.81 (2H, br s), 3.91 (2H, s), 3.20 (2H, s), 2.40 (3H, s), 1.48 (9H, s).

Workup

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

Sources & evidence

ORD record
ord-92e0ac305aa9483780760ba8386d4471
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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