Lithium Hydroxide → HCID 71543453, compound

HRID 1746419Notes

Reaction equation

HRID 1746419 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:26][CH:27]([CH3:29])[CH3:28])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][C:22]([O:24]C)=[O:23])=[CH:15][CH:14]=1)(=[O:12])=[O:11].[OH-].[Li+]>O1CCCC1.O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:26][CH:27]([CH3:29])[CH3:28])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:15][CH:14]=1)(=[O:12])=[O:11]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86731594HCID 86731594, compound

Product 1

HCID 71543453HCID 71543453, compoundYield 54.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of methyl 4-(4-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)phenyl)butanoate (10.9 mg, 0.026 mmol) in tetrahydrofuran (THF) (0.25 mL) stirred in air at RT was added a solution of lithium hydroxide (0.625 mg, 0.026 mmol) in water (0.250 mL) in one charge. The reaction mixture was stirred at 20° C. for 30 min, to ensure dissolution and then left to stand overnight. Analysis showed complete conversion. The reaction mixture was evaporated and the residue partitioned between ethyl acetate 5 mL and water 5 mL, stirring vigorously for 2 hours before separation with a hydrophilic frit. Analysis showed product to be in both layers. Both layers were separately acidified (2N hydrochloric acid, ca. 1 mL), diluted with water (2 mL) and dichloromethane (2×3 mL). The organic fractions were separated by hydrophobic frit. The appropriate fractions were combined and dried under a stream of nitrogen in the Radleys blowdown apparatus to give the two batches of the required product 5.75 mg and 3.05 mg. LCMS (M+1) 404, RT 1.27 mins.

Workup

  1. additioncharge
  2. dissolutiondissolution
  3. waitleft
  4. waitto stand overnight
  5. customThe reaction mixture was evaporated
  6. customthe residue partitioned between ethyl acetate 5 mL and water 5 mL
  7. stirringstirring vigorously for 2 hours before separation with a hydrophilic frit
  8. additiondiluted with water (2 mL) and dichloromethane (2×3 mL)
  9. customThe organic fractions were separated by hydrophobic frit
  10. customdried under a stream of nitrogen in the Radleys blowdown apparatus

Sources & evidence

ORD record
ord-80ae53d102f744258d5fe08298572efe
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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