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

HRID 1170384

반응식

HRID 1170384 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
5 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-81bacfab769c46d4a0fcb7aad15654df
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825264B2

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