Potassium Carbonate → Tert-butyl 6-(benzenesulfonylmethyl)-3-bromo-2-carbamoylmethoxybenzoate

HRID 1778363Notes

Reaction equation

HRID 1778363 reaction equation
Br[CH2:2][C:3]([NH2:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].[C:12]1([S:18]([CH2:21][C:22]2[C:27]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[C:26]([OH:35])[C:25]([Br:36])=[CH:24][CH:23]=2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CC(C)=O>[C:12]1([S:18]([CH2:21][C:22]2[C:27]([C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])=[C:26]([O:35][CH2:2][C:3](=[O:4])[NH2:5])[C:25]([Br:36])=[CH:24][CH:23]=2)(=[O:19])=[O:20])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 66686379Tert-butyl 6-(benzenesulfonylmethyl)-3-bromo-2-hydroxybenzoate2×

Product 1

HCID 66685566Tert-butyl 6-(benzenesulfonylmethyl)-3-bromo-2-carbamoylmethoxybenzoateYield 77.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Bromoacetamide (0.12 g) and potassium carbonate (0.28 g) were added to solution of tert-butyl 6-(benzenesulfonylmethyl)-3-bromo-2-hydroxybenzoate (Intermediate 38, 0.34 g) in acetone (10 mL) and the mixture was stirred for 18 hours. The mixture was evaporated to dryness and the residue was suspended in DCM and the insoluble material was removed by filtration. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and pentane with a gradient of 50-60% to give tert-butyl 6-(benzenesulfonylmethyl)-3-bromo-2-carbamoylmethoxybenzoate (0.30 g).

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe insoluble material was removed by filtration
  3. customThe filtrate was evaporated to dryness
  4. customthe residue was purified by chromatography on silica
  5. washeluting with a mixture of ethyl acetate and pentane with a gradient of 50-60%

Sources & evidence

ORD record
ord-e49b6ba46d004dacbe692cda2659d3a1
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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