Pyridine → HCID 86744400, compound

HRID 1111013Notes

Reaction equation

HRID 1111013 reaction equation
[N-:1]=[C:2]=[O:3].[C:4]([O:8][C:9](=[O:12])[CH2:10][NH2:11])([CH3:7])([CH3:6])[CH3:5].[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl.N[OH:21].C(OC)(OC)OC.[CH2:29]1COC[CH2:30]1>CO>[OH:21][N:13]=[CH:18][C:17]1[CH:30]=[CH:29][C:14]([NH:1][C:2]([NH:11][CH2:10][C:9]([O:8][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:12])=[O:3])=[CH:15][CH:16]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 8028Tetrahydrofuran2×HCID 9005Trimethyl orthoformateHCID 443297Hydroxyamine hydrochlorideHCID 86742135HCID 86742135, compound

Product 1

HCID 86744400HCID 86744400, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.1 mol of p-aminobenzaldehyde ethylene glycol acetal in 100 mL of anhydrous THF is added dropwise over 10 minutes to a solution of 0.1 mol of glycine tert-butyl ester isocyanate and 0.35 mol pyridine in 100 mL THF at room temperature under N2. The reaction mixture is stirred at room temperature for 2 hours. After 2 hours the solvent is removed by rotary evaporator. A solution of 0.11 mmol hydroxylamine hydrochloride and 0.1 mol trimethyl orthoformate in CH3OH is added, and the reaction mixture is heated to reflux under N2 for 1 hour. The reaction mixture is reduced to about 1/4 volume by rotary evaporator, and water is added. The product, N-[4-(hydroxyiminomethyl)phenyl]-N'-tert-butoxycarbonylmethylurea, is isolated by filtration and dried in vacuo.

Workup

  1. customAfter 2 hours the solvent is removed by rotary evaporator
  2. temperaturethe reaction mixture is heated
  3. temperatureto reflux under N2 for 1 hour
  4. customThe reaction mixture is reduced to about 1/4 volume by rotary evaporator, and water
  5. additionis added

Sources & evidence

ORD record
ord-ab7c2024ccb143f895ff072f9723e4bd
Source dataset
uspto-grants-1990_12
Patent number
US04977272

Reaction notes

Loading…