Sodium Hydroxide → HCID 76493621, compound

HRID 538292Notes

Reaction equation

HRID 538292 reaction equation
C(OC(N1[C:12](=[O:13])[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[N:16]=2)([CH3:14])[N:10](C(OC(C)(C)C)=O)C1=O)=O)(C)(C)C.[OH-:30].[Na+]>CCOC(C)=O.CO>[NH2:10][C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[N:16]=1)([CH3:14])[C:12]([OH:13])=[O:30]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86668007HCID 86668007, compound

Product 1

HCID 76493621HCID 76493621, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(6-bromo-pyridin-2-yl)-4-methyl-2,5-dioxo-imidazolidine-1,3-dicarboxylic acid di-tert-butyl ester (31.53 g, 67.0 mmol) in 2.5M aq. NaOH soln. (215 ml) was refluxed for 40 h. The reaction mixture was diluted with EtOAc (100 ml) and filtered. The filtrates were separated and the org. layer was washed with H2O. The combined aq. layers were evaporated to dryness to leave a solid that was suspended in MeOH (350 ml) and stirred for 30 min. The suspension was filtered and the white precipitate was washed with MeOH. The filtrates were evaporated to leave a pale orange solid which was used for the next step without further purification.

Workup

  1. temperature(215 ml) was refluxed for 40 h
  2. filtrationfiltered
  3. customThe filtrates were separated
  4. washlayer was washed with H2O
  5. customThe combined aq. layers were evaporated to dryness
  6. customto leave a solid
  7. filtrationThe suspension was filtered
  8. washthe white precipitate was washed with MeOH
  9. customThe filtrates were evaporated
  10. customto leave a pale orange solid which
  11. customwas used for the next step without further purification

Sources & evidence

ORD record
ord-4decde819ab64daeae83f43ea4c689a8
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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