Hydrochloric Acid → HCID 25183517, compound

HRID 1925715Notes

Reaction equation

HRID 1925715 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:20]([O:22]C)=[O:21])(=[O:13])=[O:12])=[C:7]([Cl:24])[CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>O1CCCC1>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:20]([OH:22])=[O:21])(=[O:12])=[O:13])=[C:7]([Cl:24])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59180392HCID 59180392, compound

Product 1

HCID 25183517HCID 25183517, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 71 (1.75 g; 4.5 mmol) in tetrahydrofuran (25 mL) was added aqueous sodium hydroxide (20 mL; 6M) and then heated at 70° C. for 24 hours. The reaction mixture was allowed to cool to room temperature and then acidified to pH 2 with concentrated hydrochloric acid. The organic solvent was removed under reduced pressure and the resulting aqueous solution was extracted with chloroform (3×20 mL). The organic extracts were combined and successively washed with water and aqueous saturated sodium chloride, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield the title compound as an off-white solid (1.57 g).

Workup

  1. temperatureto cool to room temperature
  2. customThe organic solvent was removed under reduced pressure
  3. extractionthe resulting aqueous solution was extracted with chloroform (3×20 mL)
  4. washsuccessively washed with water and aqueous saturated sodium chloride
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-626c9fac4ebe4aad841f444a1fa29fa4
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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