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

HRID 548678Notes

Reaction equation

HRID 548678 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-523d08df92b54da8b4195977ad58991d
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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