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

HRID 1505769노트

반응식

HRID 1505769 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1e057f0fd1ca46ac82da946409a3220a
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216968B2

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