Hydrochloric Acid → HCID 19600266, compound

HRID 611256Notes

Reaction equation

HRID 611256 reaction equation
[C:1]([C:9]1[CH:29]=[CH:28][C:12]([C:13]([N:15]2[CH2:20][CH2:19][C:18]3[CH:21]=[C:22]([C:24]([O:26]C)=[O:25])[O:23][C:17]=3[CH2:16]2)=[O:14])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCCC1.[OH-].[Na+]>[C:1]([C:9]1[CH:10]=[CH:11][C:12]([C:13]([N:15]2[CH2:20][CH2:19][C:18]3[CH:21]=[C:22]([C:24]([OH:26])=[O:25])[O:23][C:17]=3[CH2:16]2)=[O:14])=[CH:28][CH:29]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 19600240HCID 19600240, compound

Product 1

HCID 19600266HCID 19600266, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 126 mg (0.324 mmol) of methyl 6-(4-benzoylbenzoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine-2-carboxylate in 10 ml of tetrahydrofuran, 1 ml of 2 N aqueous sodium hydroxide was added, followed by stirring at room temperature for 1 day. The reaction mixture was acidified with 10 ml of 1 N hydrochloric acid and extracted with diethyl ether 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate/methanol=4/1 to chloroform/methanol=1/1) to yield the desired product.

Workup

  1. extractionextracted with diethyl ether 3 times
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate/methanol=4/1 to chloroform/methanol=1/1)

Sources & evidence

ORD record
ord-3d4203d0a7e94fc0b05be808b7d77e36
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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