Lithium Hydroxide → HCID 25183372, compound

HRID 1925695Notes

Reaction equation

HRID 1925695 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]([C:24]#[N:25])[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:13])=[O:12])=[C:7]([C:24]#[N:25])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59180386HCID 59180386, compound

Product 1

HCID 25183372HCID 25183372, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
77.5 °C

Procedure

To a solution of 38 (220.0 mg; 0.58 mmol) in tetrahydrofuran (4 mL) and methanol (1 mL) was added aqueous lithium hydroxide (1.45 mL; 2M. The reaction mixture was heated at 75-80° C. for 6 hours, allow ed 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 white solid residue was purified by preparative HPLC to yield the title compound as a white solid (110 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 white solid residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-2acdc32cef6a41fba6c528aa86dbafda
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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