Pivaloyl chloride → Methyl 2-hydroxy-6-pivalamidobenzoate

HRID 1778395노트

반응식

HRID 1778395 반응식
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)(O)[O-].[Na+].[C:18](Cl)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]>C(OCC)(=O)C.O>[C:19]([C:18]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[O:23])([CH3:22])([CH3:21])[CH3:20]

참가 물질

6

반응물 3

HCID 62493Pivaloyl chloride3회HCID 516892Sodium Bicarbonate2회HCID 21514499Methyl 2-amino-6-hydroxybenzoate

생성물 1

HCID 66686167Methyl 2-hydroxy-6-pivalamidobenzoate수율 78.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매2회

실험 절차

A solution of methyl 2-amino-6-hydroxybenzoate (prepared according to Comess et al, US2004 167128, 3.8 g) and sodium bicarbonate (2.52 g) in ethyl acetate (75 mL) and water (17.5 mL) was stirred at room temperature and pivaloyl chloride (3.51 g) was added dropwise. The resultant mixture was stirred at room temperature for 1 hour. A further amount of pivaloyl chloride (1.75 g) was added and the mixture was stirred at room temperature for 2.5 hours. A further amount of pivaloyl chloride (1 g) was added and the mixture was stirred at room temperature for 4 hours and 20 minutes. Ethyl acetate and saturated aqueous sodium bicarbonate solution were added and the layers were separated. The organic phase was washed with brine, dried (Na2SO4), filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 5-25% to give methyl 2-tert-butylcarbonylamino-6-hydroxybenzoate (4.46 g) as a white solid.

후처리

  1. stirringthe mixture was stirred at room temperature for 4 hours and 20 minutes
  2. customthe layers were separated
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was purified by chromatography on silica
  8. washeluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 5-25%

출처 및 근거

ORD 기록
ord-930c6cc44e9940e0889d56266f0c752b
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266896B2

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