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Sodium Hydroxide → N-(2-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}ethyl)-2,4-difluoro-N-(phenylmethyl)benzenesulfonamide

HRID 548678
ノート
印刷プレビュー

反応式

HRID 548678 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9](Cl)(=[O:11])=[O:10].[CH3:13][C:14]([Si:17]([CH3:30])([CH3:29])[O:18][CH2:19][CH2:20][NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:16])[CH3:15].[OH-].[Na+]>C(Cl)Cl>[CH3:16][C:14]([Si:17]([CH3:30])([CH3:29])[O:18][CH2:19][CH2:20][N:21]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[S:9]([C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])(=[O:11])=[O:10])([CH3:13])[CH3:15]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 27342732,4-Difluorobenzenesulfonyl ChlorideHCID 21993563Benzyl({2-[(tert-butyldimethylsilyl)oxy]ethyl})amine

生成物 1

HCID 57663174N-(2-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}ethyl)-2,4-difluoro-N-(phenylmethyl)benzenesulfonamide収率 103.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The following process was carried out according to literature precedent (JOC, 1988, 53 (7), 1372). 2,4-Difluorobenzenesulphonyl chloride (436 mg, 2.05 mmol) was added slowly to a stirred solution of 2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-N-(phenylmethyl)ethanamine (600 mg, 2.26 mmol) in a 1:1 mixture of 10% sodium hydroxide solution and DCM (80 mL) at 0° C. The reaction mixture was allowed to warm up to RT and left to stir for 5 hours. The phases were separated and the aqueous phase was extracted with DCM (3×50 mL). The combined extracts were dried (MgSO4), filtered and evaporated to afford the title compound as a colourless oil (939 mg).

後処理

  1. waitleft
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with DCM (3×50 mL)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-523d08df92b54da8b4195977ad58991d
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07943607B2

反応ノート

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