Lithium Hydroxide → HCID 25183376, compound

HRID 1925700Notes

Reaction equation

HRID 1925700 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:20]([O:22]C)=[O:21])(=[O:13])=[O:12])=[C:7]([CH3:24])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>O1CCCC1.CO>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:20]([OH:22])=[O:21])(=[O:12])=[O:13])=[C:7]([CH3:24])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59180413HCID 59180413, compound

Product 1

HCID 25183376HCID 25183376, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
77.5 °C

Procedure

To a solution of 48 (256.0 mg; 0.69 mmol) in tetrahydrofuran (15 mL) and methanol (3 mL) was added aqueous lithium hydroxide (3.5 mL; 2M). The reaction mixture was heated at 75-80° C. for 6 hours, allowed to cool to room temperature and then concentrated under reduced pressure. The resulting residue was dissolved in chloroform (15 mL) and washed with aqueous hydrochloric acid (2×10 mL; 2N). The organic phase was dried over magnesium sulfate, filtered and the solvent evaporated under reduced pressure. The crude beige residue was purified by automated silica gel column chromatography (Biotage®) eluting with ethyl acetate/hexanes (0 to 10% v/v over 350 mL gradient elution) to give the title product as a white solid (187 mg).

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resulting residue was dissolved in chloroform (15 mL)
  4. washwashed with aqueous hydrochloric acid (2×10 mL; 2N)
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure
  8. customThe crude beige residue was purified by automated silica gel column chromatography (Biotage®)
  9. washeluting with ethyl acetate/hexanes (0 to 10% v/v over 350 mL gradient elution)

Sources & evidence

ORD record
ord-5b178449de264da88a0ef024ebbc3bf3
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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