Tetrabutylammonium Fluoride → Methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoate

HRID 927924ノート

反応式

HRID 927924 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([NH:22][C:23]1[C:32]([C:33]2[CH:37]=[CH:36][O:35][C:34]=2[CH2:38][O:39][Si](C(C)(C)C)(C)C)=[CH:31][CH:30]=[C:29]([NH:47][C:48](=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50])[C:24]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:21])[CH3:20]>C1COCC1>[C:19]([NH:22][C:23]1[C:32]([C:33]2[CH:37]=[CH:36][O:35][C:34]=2[CH2:38][OH:39])=[CH:31][CH:30]=[C:29]([NH:47][C:48](=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50])[C:24]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:21])[CH3:20]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 90071968Methyl 2-acetylamino-3-[2-(tert-butyldimethylsilanyloxymethyl)-furan-3-yl]-6-(2,2-dimethylpropionylamino)benzoate2 回

生成物 1

HCID 70984627Methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoate収率 60.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Tetrabutylammonium fluoride (1M solution in THF, 1.1 mL) was added to a stirred, cooled solution of methyl 2-acetylamino-3-[2-(tert-butyldimethylsilanyloxymethyl)-furan-3-yl]-6-(2,2-dimethylpropionylamino)benzoate (Intermediate 34, 0.43 g) in THF (10 mL) at 0° C. and the mixture was stirred at 0° C. for 40 minutes then evaporated to dryness. The residue was partitioned between ethyl acetate and water and the organic layer was washed with brine, dried (MgSO4) and filtered. 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 0-2% to give methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoate (0.2 g) as a gum.

後処理

  1. customthen evaporated to dryness
  2. customThe residue was partitioned between ethyl acetate and water
  3. washthe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica eluting with a mixture of methanol and ethyl acetate with a gradient of 0-2%

出典と根拠

ORDレコード
ord-a1a9d103046141fd823563acadee9fe4
出典データセット
uspto-grants-2016_03
特許番号
US09290472B2

反応ノート

読み込み中…