Hydrochloric Acid → HCID 59180408, compound

HRID 1925683Notes

Reaction equation

HRID 1925683 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[S:12]([N:15]([C:19]1[CH:23]=[CH:22][S:21][C:20]=1[C:24]([O:26][CH3:27])=[O:25])COC)(=[O:14])=[O:13].Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:9])([CH3:10])[CH3:11])[CH:5]=[CH:4][C:3]=1[S:12]([NH:15][C:19]1[CH:23]=[CH:22][S:21][C:20]=1[C:24]([O:26][CH3:27])=[O:25])(=[O:13])=[O:14]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 59180438HCID 59180438, compound

Product 1

HCID 59180408HCID 59180408, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 21 (292.0 mg; 0.68 mmol) in tetrahydrofuran (5 mL) was added aqueous hydrochloric acid (3.38 mL; 6.76 mol; 2N). The reaction mixture was heated at 75° C. for 4 hours, and then additional aqueous hydrochloric acid (3.0 mL; 6N) was added and the reaction mixture further heated at reflux for 4-5 hours. The reaction mixture was allowed to cool to room temperature and then extracted with ethyl acetate (15 mL). The organic layer was separated, dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield a white solid which was purified by automated silica gel chromatography (Biotage®) eluting with ethyl acetate/hexanes (0 to 25% v/v over 400 mL gradient elution) to yield the title as an off-white solid (180 mg).

Workup

  1. temperaturethe reaction mixture further heated
  2. temperatureat reflux for 4-5 hours
  3. temperatureto cool to room temperature
  4. extractionextracted with ethyl acetate (15 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto yield a white solid which
  10. customwas purified by automated silica gel chromatography (Biotage®)
  11. washeluting with ethyl acetate/hexanes (0 to 25% v/v over 400 mL gradient elution)

Sources & evidence

ORD record
ord-cad10f2d933649ff854e4acae3393880
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

Loading…