Hydrochloric Acid → HCID 58280096, compound

HRID 2189095Notes

Reaction equation

HRID 2189095 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[C:14]3[C:21]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)=[C:20]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[O:19][C:15]=3[N:16]=[CH:17][N:18]=2)[CH:7]=1.[OH-].[Na+].Cl>O1CCOCC1>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([C:21]2[C:14]3[C:13]([O:12][C:8]4[CH:7]=[C:6]([NH:5][CH2:4][C:3]([OH:36])=[O:2])[CH:11]=[CH:10][CH:9]=4)=[N:18][CH:17]=[N:16][C:15]=3[O:19][C:20]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58280090HCID 58280090, compound

Product 1

HCID 58280096HCID 58280096, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Stir 65 mg (0.135 mmol) of N-(3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}-phenyl)glycine methyl ester, 0.27 ml of 1N sodium hydroxide solution and 2 ml of dioxane at RT overnight. Acidify the mixture with 1N hydrochloric acid and extract repeatedly with ethyl acetate/dichloromethane (1:1). Dry the combined organic phases over magnesium sulphate and concentrate. Chromatograph the residue on silica gel (eluent: dichloromethane/methanol 100:1→50:1). 16.8 mg (13.8% of theory) of the target compound are obtained as a yellowish hard oil.

Workup

  1. extractionextract repeatedly with ethyl acetate/dichloromethane (1:1)
  2. dry with materialDry the combined organic phases over magnesium sulphate
  3. concentrationconcentrate
  4. custom16.8 mg (13.8% of theory) of the target compound are obtained as a yellowish hard oil

Sources & evidence

ORD record
ord-659b3c9290ea48e8bf5f82f360e57b90
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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