Sodium Bicarbonate → HCID 58499557, compound

HRID 910269Notes

Reaction equation

HRID 910269 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C@@H:13]([C:15]2[N:19]([CH2:20][CH3:21])[C:18]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([N:29]4[CH2:38][CH2:37][C:32]5(OCC[O:33]5)[CH2:31][CH2:30]4)[CH:24]=3)=[N:17][N:16]=2)[CH3:14])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)(O)[O-].[Na+]>C1COCC1.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C@@H:13]([C:15]2[N:19]([CH2:20][CH3:21])[C:18]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([N:29]4[CH2:30][CH2:31][C:32](=[O:33])[CH2:37][CH2:38]4)[CH:24]=3)=[N:17][N:16]=2)[CH3:14])(=[O:10])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 58499782HCID 58499782, compound

Product 1

HCID 58499557HCID 58499557, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound (0.981 g) of Example 7 in THF (10 mL), 2N aqueous hydrochloric acid (8.4 mL) was added, and the mixture was stirred at room temperature for one hour. Concentrated hydrochloric acid (2 mL) was added, and the mixture was stirred at 50° C. for six hours. Saturated aqueous sodium bicarbonate was added for neutralization, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and then evaporated under reduced pressure to remove the solvent. The resulting residue was purified by column chromatography (acidic OH SiO2, ethyl acetate) and then recrystallized (chloroform-hexane) to give the titled compound (0.572 g, colorless powder).

Workup

  1. stirringthe mixture was stirred at 50° C. for six hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto remove the solvent
  8. customThe resulting residue was purified by column chromatography (acidic OH SiO2, ethyl acetate)
  9. customrecrystallized (chloroform-hexane)

Sources & evidence

ORD record
ord-5643ef884381467ba714691d6efe5544
Source dataset
uspto-grants-2011_09
Patent number
US08022091B2

Reaction notes

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