N-(5-Acetyl-2-benzyloxyphenyl)-N-benzylmethanesulfonamide → N-Benzyl-N-[2-benzyloxy-5-(2-bromoacetyl)phenyl]methanesulfonamide

HRID 2118346Notes

Reaction equation

HRID 2118346 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:8]([N:10]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:11]([CH3:14])(=[O:13])=[O:12])[CH:9]=1)(=[O:3])[CH3:2].[Br-:30].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>C1COCC1>[Br:30][CH2:2][C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:8]([N:10]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:11]([CH3:14])(=[O:13])=[O:12])[CH:9]=1)=[O:3]

Participants

4

Reactant 2

HCID 12363924N-(5-Acetyl-2-benzyloxyphenyl)-N-benzylmethanesulfonamideHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 86607679N-Benzyl-N-[2-benzyloxy-5-(2-bromoacetyl)phenyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-{5-acetyl-2-[(phenylmethyl)oxy]phenyl}-N-(phenylmethyl) methanesulfonamide (J. Med Chem 1977, 20, 687-92) (1.18 g) in THF (50 ml) was treated with phenyltrimethylammonium tribromide (1.08 g) at <10° and stirred for 6 h. The reaction mixture was quenched with chilled water and then filtered. The filtrate was partitioned between diethyl ether and water, the organic phase was dried (MgSO4) and the solvent was removed in vacuo. The mixture was purified by column chromatography on silica (SPE bond elut, gradient 0 to 45% EtOAc-cyclohexane) to afford the title compound. LCMS RT=3.48 min

Workup

  1. customThe reaction mixture was quenched with chilled water
  2. filtrationfiltered
  3. customThe filtrate was partitioned between diethyl ether and water
  4. dry with materialthe organic phase was dried (MgSO4)
  5. customthe solvent was removed in vacuo
  6. customThe mixture was purified by column chromatography on silica (SPE bond elut, gradient 0 to 45% EtOAc-cyclohexane)

Sources & evidence

ORD record
ord-8a5d6ff9f23c4a2b82f3ef71fd30b183
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

Loading…