Methanol → HCID 25183369, compound

HRID 1925721Notes

Reaction equation

HRID 1925721 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([S:14]([NH:17][C:18]2[CH:22]=[CH:21][S:20][C:19]=2[C:23]([O:25]C)=[O:24])(=[O:16])=[O:15])[CH:9]=1.[OH-].[Na+].CO>O1CCCC1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([S:14]([NH:17][C:18]2[CH:22]=[CH:21][S:20][C:19]=2[C:23]([OH:25])=[O:24])(=[O:15])=[O:16])[CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 59180460HCID 59180460, compound

Product 1

HCID 25183369HCID 25183369, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 82 (78 mg; 0.20 mmol) in tetrahydrofuran (2 mL) were added aqueous sodium hydroxide (1 mL; 2N) and methanol (0.5 mL), sequentially. The reaction mixture was heated at 60° C. for 17 hours, allowed to cool to room temperature, and then extracted with aqueous sodium hydroxide (20 mL; 2N). The aqueous layer was washed with dichloromethane (20 mL), acidified with aqueous hydrochloric acid (20 mL; 6N), and extracted with dichloromethane (30 mL). The organic layer was washed with aqueous saturated sodium chloride (20 mL), dried over magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting white solid was purified by a silica gel plug eluting with a 25% to 100% ethyl acetate gradient to yield the title compound as a white solid (36 mg).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with aqueous sodium hydroxide (20 mL; 2N)
  3. washThe aqueous layer was washed with dichloromethane (20 mL)
  4. extractionextracted with dichloromethane (30 mL)
  5. washThe organic layer was washed with aqueous saturated sodium chloride (20 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe resulting white solid was purified by a silica gel plug
  10. washeluting with a 25% to 100% ethyl acetate gradient

Sources & evidence

ORD record
ord-9c8d6829b01e4f54af84c31bda009c36
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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