Lithium Hydroxide → HCID 71543454, compound

HRID 1746424Notes

Reaction equation

HRID 1746424 reaction equation
[CH2:1]([N:5]([C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:22]=1[CH3:31])[S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19]C)=[O:18])=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH:2]([CH3:4])[CH3:3].[OH-].[Li+]>O1CCCC1.O>[CH2:1]([N:5]([C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:24]=[CH:23][C:22]=1[CH3:31])[S:6]([C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:13][CH:14]=1)(=[O:7])=[O:8])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86731595HCID 86731595, compound

Product 1

HCID 71543454HCID 71543454, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of methyl 3-(4-(N-isobutyl-N-(2-methyl-5-(trifluoromethyl)phenyl)sulfamoyl)phenyl)propanoate (15 mg, 0.033 mmol) in tetrahydrofuran (THF) (1.5 mL) at room temperature, was added a solution of lithium hydroxide (approximately 0.785 mg, 0.033 mmol—tip of spatula used) in water (1.5 mL). The reaction mixture was stirred at 20° C. for 4 hours and then stood overnight. The mixture was concentrated in vacuo then partitioned between water (2 mL) and ethyl acetate (2×5 mL). The aqueous layer was separated (hydrophilic frit) and acidified, then extracted with ethyl acetate (5 mL). The organic layer was separated (hydrophobic frit) and concentrated in vacuo to give required product, 2.4 mg. LCMS (M+1) 444, RT 1.25 mins.

Workup

  1. waitstood overnight
  2. concentrationThe mixture was concentrated in vacuo
  3. customthen partitioned between water (2 mL) and ethyl acetate (2×5 mL)
  4. customThe aqueous layer was separated (hydrophilic frit)
  5. extractionextracted with ethyl acetate (5 mL)
  6. customThe organic layer was separated (hydrophobic frit)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-98bb46eb071345d296ca5c416508310e
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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