Hydrochloric Acid → HCID 59180407, compound

HRID 1925697Notes

Reaction equation

HRID 1925697 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]([C:18]2[CH:22]=[CH:21][S:20][C:19]=2[C:23]([O:25][CH3:26])=[O:24])COC)(=[O:13])=[O:12])=[C:7]([CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl>O1CCCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:18]2[CH:22]=[CH:21][S:20][C:19]=2[C:23]([O:25][CH3:26])=[O:24])(=[O:13])=[O:12])=[C:7]([CH2:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 59180376HCID 59180376, compound

Product 1

HCID 59180407HCID 59180407, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 41 (143.0 mg; 0.32 mmol) in tetrahydrofuran (6 mL) was added aqueous hydrochloric acid (6 mL; 12 mmol; 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 an orange oil residue which was purified by automated silica gel column chromatography (Biotage®) eluting with ethyl acetate/hexanes (0 to 40% v/v over 400 mL gradient elution) to yield the title product as a clear oil (80.0 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 an orange oil residue which
  10. customwas purified by automated silica gel column chromatography (Biotage®)
  11. washeluting with ethyl acetate/hexanes (0 to 40% v/v over 400 mL gradient elution)

Sources & evidence

ORD record
ord-9689f0804fa04db5962c00fadc3f96ea
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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