Lithium Hydroxide → HCID 25183503, compound

HRID 1925680Notes

Reaction equation

HRID 1925680 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:20]([NH:23][C:24]2[CH:28]=[CH:27][S:26][C:25]=2[C:29]([O:31]C)=[O:30])(=[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].[OH-].[Li+]>O1CCCC1.CO>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:20]([NH:23][C:24]2[CH:28]=[CH:27][S:26][C:25]=2[C:29]([OH:31])=[O:30])(=[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

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59180387HCID 59180387, compound

Product 1

HCID 25183503HCID 25183503, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
77.5 °C

Procedure

To a solution of 14 (50.0 mg; 0.11 mmol) in tetrahydrofuran (1 mL) and methanol (1 mL) was added aqueous lithium hydroxide (2 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 combined organic phases were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield the title compound as a brown solid (47.2 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 combined organic phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9662231a3ad24bb18e53afcbbcde51d7
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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