Hydroxylamine → tert-Butyl N-{4-[amino(hydroxyimino)methyl]-2-fluorophenyl}glycinate

HRID 219848Notes

Reaction equation

HRID 219848 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[C:5]([F:18])[CH:4]=1)#[N:2].[NH2:19][OH:20]>CO>[NH2:2][C:1](=[N:19][OH:20])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])=[C:5]([F:18])[CH:4]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 81651672tert-Butyl N-(4-cyano-2-fluorophenyl)glycinate

Product 1

HCID 72307482tert-Butyl N-{4-[amino(hydroxyimino)methyl]-2-fluorophenyl}glycinate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl N-(4-cyano-2-fluorophenyl)glycinate obtained in Step 1 (290 mg; 1.16 mmol; 1 eq.) was dissolved in MeOH (1 mL) and hydroxylamine (0.34 mL; 5.79 mmol; 5 eq.) was added. The mixture was stirred at RT overnight. Solvents were evaporated off, affording the title product as an off-white solid, which was used further without purification (302 mg, 92%). HPLC (Method A) Rt 2.23 min (Purity: 74.2%).

Workup

  1. customSolvents were evaporated off

Sources & evidence

ORD record
ord-2d6c73a9be3341778097526a85f9b02b
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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