Tributyltin fluoride → Methyl[5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridin-3-yl]acetate

HRID 1349482ノート

反応式

HRID 1349482 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][CH:33]=1)[CH2:5][NH:6][C:7]([C:9]1[N:10]([CH2:25][CH:26]([O:29][CH3:30])[O:27][CH3:28])[CH:11]=[C:12](Br)[C:13](=[O:23])[C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:8].C([Sn](F)(CCCC)CCCC)CCC.[Si]([O:55][CH:56]([O:58][CH3:59])[CH3:57])(C(C)(C)C)(C)C.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:16]([O:15][C:14]1[C:13](=[O:23])[C:12]([CH2:57][C:56]([O:58][CH3:59])=[O:55])=[CH:11][N:10]([CH2:25][CH:26]([O:29][CH3:30])[O:27][CH3:28])[C:9]=1[C:7](=[O:8])[NH:6][CH2:5][C:4]1[CH:31]=[CH:32][CH:33]=[C:2]([Cl:1])[CH:3]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

8

反応物 4

HCID 16120Tributyltin fluorideHCID 516892Sodium BicarbonateHCID 230776861-(Tert-butyldimethylsilyloxy)-1-methoxyethaneHCID 588591313-Benzyloxy-5-bromo-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide

生成物 1

HCID 58859124Methyl[5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridin-3-yl]acetate収率 62.1%

試薬・触媒・溶媒 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a solution of 3-benzyloxy-5-bromo-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide (300 mg) obtained in Example 161, Step 2 in toluene were added under an argon stream tributyltin fluoride (518 mg), tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (58 mg), 1,1′-bis(diphenylphosphino)ferrocene (64 mg) and 1-(tert-butyldimethylsilyloxy)-1-methoxyethane (525 mg), and the mixture was stirred at 100° C. for 15 hr. After cooling to room temperature, aqueous sodium hydrogen carbonate was added to the reaction mixture and the mixture was extracted three times with ethyl acetate. The extract was dried, concentrated and purified by silica gel column chromatography (ethyl acetate) to give methyl [5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridin-3-yl]acetate (184 mg).

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. customThe extract was dried
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-86457739ccdb438694853baaa7b6936c
出典データセット
uspto-grants-2007_05
特許番号
US07211572B2

反応ノート

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