Cesium carbonate → HCID 59349465, compound

HRID 415104Notes

Reaction equation

HRID 415104 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16].CS(O[CH:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1)(=O)=O>CC(N(C)C)=O>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 37588824-Amino-3-NitrophenolHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Product 1

HCID 59349465HCID 59349465, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

Cesium carbonate (14.19 g, 43.56 mmoles, 2 equivalents) was added to a stirred solution of 4-amino-3-nitrophenol (3.35 g, 21.78 mmoles, 1 equivalent) and tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (6.69 g, 23.96 mmoles, 1.1 equivalent) in anhydrous DMA (30 ml). The stirred reaction mixture was then heated to 90° C. (thermostatically controlled heating mantle) for 22 hours. The reaction mixture was then allowed to cool to room temperature and was filtered through a plug of Celite. The reaction flask and the Celite were then washed with ethyl acetate (250 ml). The organic solution was then transferred to a separatory funnel and extracted with additional ethyl acetate (3×200 ml). The combined ethyl acetate solution was then washed with water (2×100 ml), saturated sodium chloride (2×100 ml), dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure.

Workup

  1. customThe stirred reaction mixture
  2. temperaturethermostatically controlled heating mantle) for 22 hours
  3. temperatureto cool to room temperature
  4. filtrationwas filtered through a plug of Celite
  5. washThe reaction flask and the Celite were then washed with ethyl acetate (250 ml)
  6. customThe organic solution was then transferred to a separatory funnel
  7. extractionextracted with additional ethyl acetate (3×200 ml)
  8. washThe combined ethyl acetate solution was then washed with water (2×100 ml), saturated sodium chloride (2×100 ml)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-81efce5dc44948fe9bf443b6dd334eba
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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