Dimethylformamide → Tert-butyl 6-(benzenesulfonylmethyl)-3-bromo-2-(2-hydroxy-acetylamino)benzoate
Reaction equation
[OH-].[Na+].[C:3]1([S:9]([CH2:12][C:13]2[C:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:17](OCC(=O)N)[C:16]([Br:31])=[CH:15][CH:14]=2)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:32](OCC)(=[O:34])C.C(=O)([O-])O.[Na+].C[N:44]([CH:46]=[O:47])C>>[C:3]1([S:9]([CH2:12][C:13]2[C:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:17]([NH:44][C:46](=[O:47])[CH2:32][OH:34])[C:16]([Br:31])=[CH:15][CH:14]=2)(=[O:10])=[O:11])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1Participants
6
Procedure
Sodium hydroxide (0.14 g) was added to a solution of tert-butyl 6-(benzenesulfonylmethyl)-3-bromo-2-carbamoylmethoxybenzoate (Intermediate 37, 0.33 g) in DMF (5 mL) and the mixture was stirred for 7 hours. Ethyl acetate and a saturated aqueous solution of sodium hydrogen carbonate were added to the mixture and the organic layer was separated, washed with water and brine, dried (Na2SO4) and filtered. 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 20-100%, to give tert-butyl 6-(benzenesulfonylmethyl)-3-bromo-2-(2-hydroxyacetylamino)-benzoate (0.17 g) as a yellow oil.
Workup
- customthe organic layer was separated
- washwashed with water and brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customThe filtrate was evaporated to dryness
- customthe residue was purified by chromatography on silica
- washeluting with a mixture of ethyl acetate and pentane with a gradient of 20-100%
Sources & evidence
- ORD record
- ord-cb59b3460a4e41fa9d553ada9ad01e8f
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266896B2
Reaction notes
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