Hydrochloric Acid → HCID 59180387, compound

HRID 1925679Notes

Reaction equation

HRID 1925679 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:20]([N:23]([C:27]2[CH:31]=[CH:30][S:29][C:28]=2[C:32]([O:34][CH3:35])=[O:33])COC)(=[O:22])=[O:21])=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([N:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Cl>O1CCCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:20]([NH:23][C:27]2[CH:31]=[CH:30][S:29][C:28]=2[C:32]([O:34][CH3:35])=[O:33])(=[O:21])=[O:22])=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([N:17]([CH3:18])[CH3:19])=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 59180399HCID 59180399, compound

Product 1

HCID 59180387HCID 59180387, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 13 (150.0 mg; 0.30 mmol) in tetrahydrofuran (6 mL) was added aqueous hydrochloric acid (1.0 mL; 2.0 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 phase was dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and the resulting white solid residue 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 (50.9 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. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe resulting white solid residue was purified by automated silica gel column chromatography (Biotage®)
  9. washeluting with ethyl acetate/hexanes (0 to 30% v/v over 400 mL gradient elution)

Sources & evidence

ORD record
ord-a7532e98aeef42ba9e22420b100e998d
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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