Hydrochloric Acid → HCID 59853078, compound

HRID 1670325Notes

Reaction equation

HRID 1670325 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[C:16]([F:17])=[CH:15][C:14]([NH:18][C:19](=[O:26])[CH2:20][C:21]([O:23]CC)=[O:22])=[C:13]([F:27])[CH:12]=2)[CH:7]=[CH:6][N:5]=1)(=[O:3])[NH2:2].[OH-].[Na+].Cl>CO>[C:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[C:16]([F:17])=[CH:15][C:14]([NH:18][C:19](=[O:26])[CH2:20][C:21]([OH:23])=[O:22])=[C:13]([F:27])[CH:12]=2)[CH:7]=[CH:6][N:5]=1)(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59852995HCID 59852995, compound

Product 1

HCID 59853078HCID 59853078, compoundYield 112.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a heterogeneous mixture of ethyl 3-(4-(2-carbamoylpyridin-4-yloxy)-2,5-difluorophenylamino)-3-oxopropanoate (305 mg, 0.80 mmol) in MeOH (8 mL) was added aqueous 1 M NaOH (1.70 mL, 1.70 mmol). After one hour of stirring, the mixture was acidified with aqueous 1N HCl (5 mL). The reaction was extracted with EtOAc before the combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to afford the title compound (317 mg) which was used without further purification. HRMS (ESI+), 352.0745 (M+H)+ calcd., 352.0752 (M+H)+ found.

Workup

  1. extractionThe reaction was extracted with EtOAc before the combined organic layers
  2. dry with materialwere dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a2a7c9bc6db4b61b9493b4e27d54c07
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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