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

HRID 1170384Notes

Reaction equation

HRID 1170384 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
5 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-81bacfab769c46d4a0fcb7aad15654df
Source dataset
uspto-grants-2010_11
Patent number
US07825264B2

Reaction notes

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