Methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoate → methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-[cis-(2RS,3RS)-2-(hydroxymethyl)tetrahydrofuran-3-yl]benzoate

HRID 927923ノート

反応式

HRID 927923 の反応式
[C:1]([NH:4][C:5]1[C:14]([C:15]2[CH:19]=[CH:18][O:17][C:16]=2[CH2:20][OH:21])=[CH:13][CH:12]=[C:11]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2].[H][H]>O1CCOCC1.C(O)(=O)C.[OH-].[OH-].[Pd+2]>[C:1]([NH:4][C:5]1[C:14]([C@H:15]2[CH2:19][CH2:18][O:17][C@H:16]2[CH2:20][OH:21])=[CH:13][CH:12]=[C:11]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2]

参加物

6

反応物 2

HCID 70984627Methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoate2 回HCID 178418361HCID 178418361、化合物

生成物 1

HCID 70983847methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-[cis-(2RS,3RS)-2-(hydroxymethyl)tetrahydrofuran-3-yl]benzoate収率 69.3%

試薬・触媒・溶媒 3

HCID 9942167Palladium hydroxide触媒HCID 176Acetic Acid溶媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoate (Intermediate 38, 0.2 g) in dioxane (4 mL) and acetic acid (1 mL) was treated under an atmosphere of nitrogen with palladium hydroxide on carbon (10%, 0.03 g). The nitrogen was replaced by hydrogen and the mixture was stirred under an atmosphere of hydrogen overnight. The mixture was filtered through Celite and the pad was washed thoroughly with ethyl acetate. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of methanol and ethyl acetate with a gradient of 0-10% to give methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-[cis-(2RS,3RS)-2-(hydroxymethyl)tetrahydrofuran-3-yl]benzoate (0.14 g) as a white solid.

後処理

  1. filtrationThe mixture was filtered through Celite
  2. washthe pad was washed thoroughly with ethyl acetate
  3. customThe filtrate was evaporated to dryness
  4. customthe residue was purified by chromatography on silica eluting with a mixture of methanol and ethyl acetate with a gradient of 0-10%

出典と根拠

ORDレコード
ord-4ab099e12fdc4939a777b4c08bdd6a57
出典データセット
uspto-grants-2016_03
特許番号
US09290472B2

反応ノート

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