Sodium Carbonate → HCID 53241610, compound

HRID 1023594Notes

Reaction equation

HRID 1023594 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([NH:19][C@@H:20]([C:22]([OH:24])=O)[CH3:21])=[O:18])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].C(=O)([O-])[O-].[Na+].[Na+]>Cl>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[CH:11]=[CH:12][C:13]([N:16]3[C:22](=[O:24])[C@@H:20]([CH3:21])[NH:19][C:17]3=[O:18])=[CH:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 68322495HCID 68322495, compound2×

Product 1

HCID 53241610HCID 53241610, compoundYield 12.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-[({4-[(3-chloro-4-fluorophenyl)oxy]phenyl}amino)carbonyl]-D-alanine (Intermediate 9, 352 mg) in 15 mL of 3N HCl was heated at 100° C. for 16 hours. Then sodium carbonate was added and the mixture was adjusted to pH=8. The mixture was extracted with ethyl acetate (3 times 50 mL) and the combined organic phases were washed with brine and dried over magnesium sulphate. Removal of the solvent afforded a residue which was purified by column chromatography (MeOH/DCM=1/50) to give 42 mg of the title compound as a white solid.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3 times 50 mL)
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried over magnesium sulphate
  4. customRemoval of the solvent
  5. customafforded a residue which
  6. customwas purified by column chromatography (MeOH/DCM=1/50)

Sources & evidence

ORD record
ord-bc5d07f1c58a4dd5a5ae52ae9cf3690b
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

Loading…