Pivaloyl chloride → Methyl 2-hydroxy-6-pivalamidobenzoate

HRID 2200345노트

반응식

HRID 2200345 반응식
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[NH2:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[C:10]=1[C:11]([O:13][CH3:14])=[O:12].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O>[CH3:1][C:2]([CH3:7])([CH3:6])[C:3]([NH:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[O:4]

참가 물질

6

반응물 3

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

생성물 1

HCID 66686167Methyl 2-hydroxy-6-pivalamidobenzoate수율 96.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매2회

실험 절차

Trimethylacetyl chloride (3.69 g) was added to a mixture of methyl 2-amino-6-hydroxybenzoate (prepared according to Comess et al, US2004 0167128, 3.99 g) and sodium bicarbonate (2.57 g) in ethyl acetate (77 mL) and water (18 mL). The reaction mixture was stirred at room temperature for 1 hour. A further amount of trimethylacetyl chloride (1.85 g) was added and the mixture was stirred for 1 hour. A further amount of trimethylacetyl chloride (0.920 g) was added and the mixture was stirred for 30 minutes. The mixture was diluted with ethyl acetate, the layers were separated and the organic layer was dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and 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-(2,2-dimethylpropionylamino)-6-hydroxybenzoate (5.79 g) as a white solid.

후처리

  1. stirringthe mixture was stirred for 1 hour
  2. stirringthe mixture was stirred for 30 minutes
  3. customthe layers were separated
  4. dry with materialthe organic layer was dried (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-1b5685dc8b9d4e0d84b343c8484b55d7
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359369B2

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