Lithium Hydroxide → HCID 25183655, compound

HRID 1925684Notes

Reaction equation

HRID 1925684 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[S:12]([NH:15][C:16]1[CH:20]=[CH:19][S:18][C:17]=1[C:21]([O:23]C)=[O:22])(=[O:14])=[O:13].[OH-].[Li+]>O1CCCC1.CO>[C:8]([C:6]1[CH:5]=[CH:4][C:3]([S:12]([NH:15][C:16]2[CH:20]=[CH:19][S:18][C:17]=2[C:21]([OH:23])=[O:22])(=[O:13])=[O:14])=[C:2]([Cl:1])[CH:7]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59180408HCID 59180408, compound

Product 1

HCID 25183655HCID 25183655, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
77.5 °C

Procedure

To a solution of 22 (272.0 mg; 0.73 mmol) in tetrahydrofuran (8 mL) and methanol (2 mL) was added aqueous lithium hydroxide (4 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 concentrated under reduced pressure to yield the title compound as a white solid (237 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. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-88d300b5af0d45f5a810ebc5c008bf00
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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