Pivaloyl chloride → Methyl 2-hydroxy-6-pivalamidobenzoate

HRID 715974ノート

反応式

HRID 715974 の反応式
[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+]>O.C(OCC)(=O)C>[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]

参加物

6

反応物 3

HCID 62493Pivaloyl chloride2 回HCID 516892Sodium BicarbonateHCID 21514499Methyl 2-amino-6-hydroxybenzoate

生成物 1

HCID 66686167Methyl 2-hydroxy-6-pivalamidobenzoate収率 64.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Trimethylacetyl chloride (5.57 g) was added dropwise to a vigorously stirred mixture of methyl 2-amino-6-hydroxybenzoate (prepared according to Comess et al, US2004 0167128, 5.15 g) and sodium bicarbonate (7.76 g) in a mixture of water (40 mL) and ethyl acetate (100 mL) and the mixture was stirred for one hour. Further trimethylacetyl chloride (5.57 g) was added and the mixture stirred overnight. The organic layer was separated, dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and the residue was triturated with pentane. The solid was collected by filtration and purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-25% to give methyl 2-(2,2-dimethyl-propionylamino)-6-hydroxy-benzoate (4.96 g) as a white solid.

後処理

  1. stirringthe mixture stirred overnight
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was triturated with pentane
  7. filtrationThe solid was collected by filtration
  8. custompurified by chromatography on silica
  9. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-25%

出典と根拠

ORDレコード
ord-0afc0b8d38c54f139c24c9e0b0e6914d
出典データセット
uspto-grants-2015_11
特許番号
US09187494B2

反応ノート

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