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

HRID 1505769ノート

反応式

HRID 1505769 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1e057f0fd1ca46ac82da946409a3220a
出典データセット
uspto-grants-2015_12
特許番号
US09216968B2

反応ノート

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