O-ethylhydroxylamine hydrochloride → HCID 89601426, compound

HRID 570915Notes

Reaction equation

HRID 570915 reaction equation
[C:1]([N:4]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[N:5]1[CH2:10][C:9]([CH:11]=O)=[N:8][N:7]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:6]1=[O:20])(=[O:3])[CH3:2].C([O-])(=O)C.[Na+].Cl.[CH2:34]([O:36][NH2:37])[CH3:35]>CCO>[C:1]([N:4]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[N:5]1[CH2:10][C:9](/[CH:11]=[N:37]/[O:36][CH2:34][CH3:35])=[N:8][N:7]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[C:6]1=[O:20])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 517045Sodium AcetateHCID 89601756HCID 89601756, compound

Product 1

HCID 89601426HCID 89601426, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of tert-butyl 4-[acetyl(tert-butoxycarbonyl)amino]-6-formyl-3-oxo-5H-1,2,4-triazine-2-carboxylate (192 mg, 0.500 mmol) and sodium acetate (45 mg, 0.55 mmol) in EtOH (1.0 mL) at room temperature was added O-ethylhydroxylamine HCl-salt (54 mg, 0.55 mmol). The mixture was heated to 70° C. and stirred for 2 h. The obtained reaction mixture was filtered hot and the solid residual washed with EtOH. The filtrate was concentrated to give the desired product which was used without further purification. LCMS (Method I) RT 1.94 min. [M+Na]+ 450.

Workup

  1. customThe obtained reaction mixture
  2. filtrationwas filtered hot
  3. washthe solid residual washed with EtOH
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b1c458658af54ea59dbe546f4c61b6b7
Source dataset
uspto-grants-2015_05
Patent number
US09024019B2

Reaction notes

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