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

HRID 1170384

Reaktionsgleichung

Reaktionsgleichung von HRID 1170384
[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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 86621947Tert-butyl [(4-fluorophenyl)(toluene-4-sulfonyl)methyl]carbamateAusbeute 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-81bacfab769c46d4a0fcb7aad15654df
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07825264B2

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