Acetyl chloride → Methyl 2-acetylamino-3-[2-(tert-butyldimethylsilanyloxymethyl)-furan-3-yl]-6-(2,2-dimethylpropionylamino)benzoate

HRID 927925ノート

反応式

HRID 927925 の反応式
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[C:15]([C:16]2[CH:20]=[CH:19][O:18][C:17]=2[CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[CH:14][CH:13]=[C:12]([NH:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[C:7]=1[C:8]([O:10][CH3:11])=[O:9]>C(Cl)Cl.N1C=CC=CC=1>[C:1]([NH:5][C:6]1[C:15]([C:16]2[CH:20]=[CH:19][O:18][C:17]=2[CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[CH:14][CH:13]=[C:12]([NH:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[C:7]=1[C:8]([O:10][CH3:11])=[O:9])(=[O:3])[CH3:2]

参加物

5

反応物 2

HCID 6367Acetyl chlorideHCID 90071896Methyl 2-amino-3-[2-(tert-butyldimethylsilanyloxymethyl)furan-3-yl]-6-(2,2-dimethylpropionylamino)benzoate2 回

生成物 1

HCID 90071968Methyl 2-acetylamino-3-[2-(tert-butyldimethylsilanyloxymethyl)-furan-3-yl]-6-(2,2-dimethylpropionylamino)benzoate

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

Acetyl chloride (0.09 mL) was added to a stirred solution of methyl 2-amino-3-[2-(tert-butyldimethylsilanyloxymethyl)furan-3-yl]-6-(2,2-dimethylpropionylamino)-benzoate (Intermediate 35, 0.47 g) in DCM (5 mL) and pyridine (0.16 mL) and the mixture was stirred at room temperature for 1 hour. The mixture was diluted with DCM and washed with water and 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 ethyl acetate and cyclohexane with a gradient of 20-50% to give methyl 2-acetylamino-3-[2-(tert-butyldimethylsilanyloxymethyl)-furan-3-yl]-6-(2,2-dimethylpropionylamino)benzoate (0.442 g) as a colourless foam.

後処理

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 20-50%

出典と根拠

ORDレコード
ord-e6897daee7684f769bb187314220ea53
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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