Sodium Carbonate → HCID 53241611, compound

HRID 1023595Notes

Reaction equation

HRID 1023595 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 68322496HCID 68322496, compound2×

Product 1

HCID 53241611HCID 53241611, compoundYield 12%

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]-L-alanine (Intermediate 10, 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 (3×50 mL). The combined organic phases were washed with brine and dried with magnesium sulphate. Removal of the solvent afforded crude compound which was purified by column chromatography (MeOH/DCM=1/50) to give 40 mg of the title compound as a white solid.

Workup

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

Sources & evidence

ORD record
ord-3d4aad931af24a82b8459d73e902396e
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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