Hydrochloric Acid → HCID 59853078, compound

HRID 2237294Notes

Reaction equation

HRID 2237294 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-47150ad158194b6fb7a61e743ecbef38
Source dataset
uspto-grants-2010_05
Patent number
US07714138B2

Reaction notes

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