Cesium carbonate → HCID 68862791, compound

HRID 898884Notes

Reaction equation

HRID 898884 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([NH:12][C:13](=[O:15])[CH3:14])[CH2:6][CH2:5]2.C([O-])([O-])=O.[Cs+].[Cs+].Br[C:23]([CH3:32])([CH3:31])[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>CN(C=O)C.CCOC(C)=O>[C:27]([O:26][C:24](=[O:25])[C:23]([O:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH:7]([NH:12][C:13](=[O:15])[CH3:14])[CH2:6][CH2:5][C:4]=2[CH:3]=1)([CH3:32])[CH3:31])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 90290tert-Butyl 2-bromo-2-methylpropionateHCID 19855477HCID 19855477, compound

Product 1

HCID 68862791HCID 68862791, compoundYield 69.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of N-(6-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide (0.439 g; 2.1 mmol) in DMF (6 mL) is added Cs2CO3 (1.7 g; 5.2 mmol) and tert-butyl 2-bromoisobutyrate (2.1 mL; 9.4 mmol) and the reaction mixture was stirred at 100° C. for 18 h. The reaction was cooled to RT, diluted with EtOAc, washed with H2O, brine, dried over Na2SO4, filtered, and the solvent removed under reduced pressure to provide a crude oil, which was purified by flash chromatography (SiO2) eluting with a hexanes-EtOAc gradient to afford 0.51 g (69%) of 2-(6-acetylamino-5,6,7,8-tetrahydronaphthalen-2-yloxy)-2-methylpropionic acid tert-butyl ester as an oil.

Workup

  1. temperatureThe reaction was cooled to RT
  2. washwashed with H2O, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customto provide a crude oil, which
  7. customwas purified by flash chromatography (SiO2)
  8. washeluting with a hexanes-EtOAc gradient

Sources & evidence

ORD record
ord-f0716564ee484636aa0dfd1e6bbccd3d
Source dataset
uspto-grants-2008_04
Patent number
US07351857B2

Reaction notes

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