Diisopropylethylamine → Methyl 2-amino-3-[(methoxyacetyl)amino]benzoate

HRID 1505769Notes

Reaction equation

HRID 1505769 reaction equation
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(N(CC)C(C)C)(C)C.[CH3:22][O:23][CH2:24][C:25](Cl)=[O:26].C(=O)(O)[O-].[Na+]>C1COCC1>[NH2:1][C:2]1[C:11]([NH:12][C:25](=[O:26])[CH2:24][O:23][CH3:22])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 516892Sodium BicarbonateHCID 5718252,3-Diaminobenzoic acid methyl ester

Product 1

HCID 90229318Methyl 2-amino-3-[(methoxyacetyl)amino]benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of methyl 2,3-diaminobenzoate (3.0 g) in THF (50 mL) was added N,N-diisopropylethylamine (4.0 mL). The solution was stirred under ice-cooling, methoxyacetyl chloride (1.81 mL) in THF (10 mL) was added dropwise slowly, and it was stirred for 3 hours at the same temperature. To the reaction mixture was added saturated aqueous sodium bicarbonate, and THF was removed under reduced pressure. To the residue was added saturated aqueous sodium bicarbonate, and it was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified on silica gel column chromatography to obtain the titled compound (3.60 g) as pale yellow powder.

Workup

  1. temperaturecooling
  2. stirringit was stirred for 3 hours at the same temperature
  3. customwas removed under reduced pressure
  4. additionTo the residue was added saturated aqueous sodium bicarbonate, and it
  5. extractionwas extracted with ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified on silica gel column chromatography

Sources & evidence

ORD record
ord-1e057f0fd1ca46ac82da946409a3220a
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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