Hydrochloric Acid → HCID 59180429, compound

HRID 1925681Notes

Reaction equation

HRID 1925681 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]([C:27]2[CH:28]=[N:29][CH:30]=[N:31][CH:32]=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]([C:27]2[CH:32]=[N:31][CH:30]=[N:29][CH:28]=2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 59180420HCID 59180420, compound

Product 1

HCID 59180429HCID 59180429, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 17 (80.0 mg; 0.17 mmol) in tetrahydrofuran (5 mL) was added aqueous hydrochloric acid (5.0 mL; 10.0 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. The resulting crude clear oil was purified by automated silica gel column chromatography (Biotage®) eluting with ethyl acetate/hexanes (0 to 30% v/v over 400 mL gradient elution) to give the title product as a clear oil (64.0 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. customThe resulting crude clear oil was purified by automated silica gel column chromatography (Biotage®)
  10. washeluting with ethyl acetate/hexanes (0 to 30% v/v over 400 mL gradient elution)

Sources & evidence

ORD record
ord-99b65e54c29244ae8622797cd5c433ad
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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