Nitrogen → HCID 66599131, compound

HRID 2068509Notes

Reaction equation

HRID 2068509 reaction equation
N#N.[CH2:3]([O:5][C:6](=[O:11])[CH2:7][CH2:8][CH2:9]Br)[CH3:4].C(=O)([O-])[O-].[Cs+].[Cs+].[C:18]([O:22][C:23]([NH:25][C:26]1[C:35]([CH3:36])=[CH:34][C:33]([CH3:37])=[CH:32][C:27]=1[C:28]([O:30][CH3:31])=[O:29])=[O:24])([CH3:21])([CH3:20])[CH3:19]>CN(C=O)C>[C:18]([O:22][C:23]([N:25]([CH2:9][CH2:8][CH2:7][C:6]([O:5][CH2:3][CH3:4])=[O:11])[C:26]1[C:35]([CH3:36])=[CH:34][C:33]([CH3:37])=[CH:32][C:27]=1[C:28]([O:30][CH3:31])=[O:29])=[O:24])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 947NitrogenHCID 10796Cesium carbonateHCID 76300Ethyl 4-bromobutyrateHCID 66599225HCID 66599225, compound

Product 1

HCID 66599131HCID 66599131, compoundYield 113.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

Charge a 22 L flask, equipped with overhead agitation, heating mantle, condenser and a N2 purge, with DMF (10 L), ethyl-4-bromobutyrate (1.07 kg, 787.8 mL, 5.32 moles), cesium carbonate (2.92 kg, 22.5 moles), and methyl 2-(tert-butoxycarbonylamino)-3,5-dimethylbenzoate (1,000.0 g, 3.54 moles). Heat the resulting mixture to about 55° C. and stir for about 48 hours. Cool; filter off the solid; and wash the solid with MTBE (2×4 L). Combine the filtrate and the MTBE washings into a 50 L flask and cool to less than about 5° C. Add water (6 L) to quench the reaction. Separate the layers. Wash the aqueous layer with MTBE (3 L); combine the organic layers; and wash the resulting organic solution with brine (2×3 L). Dry the organic solution over Na2SO4; filter; and wash the collected solids with MTBE to yield 1.582 kg of the title compound.

Workup

  1. additionCharge a 22 L flask
  2. customequipped with overhead agitation
  3. temperatureheating mantle, condenser
  4. temperatureCool
  5. filtrationfilter off the solid
  6. washand wash the solid with MTBE (2×4 L)
  7. temperatureCombine the filtrate and the MTBE washings into a 50 L flask and cool to less than about 5° C
  8. customAdd water (6 L) to quench
  9. customthe reaction
  10. customSeparate the layers
  11. washWash the aqueous layer with MTBE (3 L)
  12. washand wash the resulting organic solution with brine (2×3 L)
  13. dry with materialDry the organic solution over Na2SO4
  14. filtrationfilter
  15. washand wash the collected solids with MTBE

Sources & evidence

ORD record
ord-0fa50ec233f648e9b8a1c00f9cc73bfe
Source dataset
uspto-grants-2012_10
Patent number
US08299060B2

Reaction notes

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