Triethylamine → [[(3-Nitrophenyl)amino]carbonyl]aminoacetic acid methyl ester

HRID 1785309

Reaction equation

HRID 1785309 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]=[C:11]=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl.[CH3:14][O:15][C:16](=[O:19])[CH2:17][NH2:18].C(N(CC)CC)C>ClCCl>[CH3:14][O:15][C:16](=[O:19])[CH2:17][NH:18][C:11]([NH:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 768353-Nitrophenyl isocyanateHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 10934009[[(3-Nitrophenyl)amino]carbonyl]aminoacetic acid methyl esterYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-nitrophenyl isocyanate (10 g, 61 mmol) and glycine methyl ester hydrochloride (8.4 g, 67 mmol, 1.1 equiv.) in dichloromethane (250 mL) was added triethylamine (10 mL, 72 mmol, 1.2 equiv.) at 0° C. The resulting solution was stirred at room temperature overnight. The resulting dark brown solution was concentrated and triturated in water to give a light yellow suspension. The suspension was filtered and the filter cake was washed with water and air-dried to give [[[(3-nitrophenyl)amino]carbonyl]aminoacetic acid methyl ester (15 g) in quantitative yield.

Workup

  1. concentrationThe resulting dark brown solution was concentrated
  2. customtriturated in water
  3. customto give a light yellow suspension
  4. filtrationThe suspension was filtered
  5. washthe filter cake was washed with water
  6. customair-dried

Sources & evidence

ORD record
ord-7cbb34cd19a849b0a82cafe0f9ba6d7b
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Linked notes

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