Chlorotrimethylsilane → Tert-butyl [(4-fluorophenyl)(toluene-4-sulfonyl)methyl]carbamate

HRID 1170384

反応式

HRID 1170384 の反応式
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10](=[O:17])([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[NH2:11].[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24]([O-])(=[O:26])=[O:25])=[CH:20][CH:19]=1.[Na+].Cl[Si](C)(C)C>C(#N)C.O>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([NH:11][C:10](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[S:24]([C:21]2[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=2)(=[O:26])=[O:25])=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 680234-FluorobenzaldehydeHCID 77922tert-Butyl carbamateHCID 3720192Sodium 4-methylbenzenesulfonate

生成物 1

HCID 86621947Tert-butyl [(4-fluorophenyl)(toluene-4-sulfonyl)methyl]carbamate収率 79.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
5 °C

実験手順

15.0 g (121 mmol) of 4-fluorobenzaldehyde were added to a solution of 21.3 g (184 mmol) of tert-butyl carbamate and 32.3 g (181 mmol) of sodium p-toluenesulfonate in 430 ml of acetonitrile under argon. While cooling to 0-10° C., 26.3 g (242 mmol) of chlorotrimethylsilane were added dropwise, and the mixture was left to stir at room temperature overnight. After addition of 400 ml of water, the precipitated product was filtered off with suction and dried in vacuo at 50° C. 36.3 g of tert-butyl [(4-fluorophenyl)(toluene-4-sulfonyl)methyl]carbamate were obtained.

後処理

  1. waitthe mixture was left
  2. filtrationthe precipitated product was filtered off with suction
  3. customdried in vacuo at 50° C

出典と根拠

ORDレコード
ord-81bacfab769c46d4a0fcb7aad15654df
出典データセット
uspto-grants-2010_11
特許番号
US07825264B2

関連ノート

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