Sodium Carbonate → HCID 53241611, compound

HRID 1505400Notes

Reaction equation

HRID 1505400 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-f8265c976a614bd28c6ab7d47fba8d2e
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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