Hydrochloric Acid → HCID 71543455, compound

HRID 1746426Notes

Reaction equation

HRID 1746426 reaction equation
[CH2:1]([N:5]([C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:25]=1[CH3:34])[S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([CH3:23])([CH3:22])[C:17]([O:19]CC)=[O:18])=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH:2]([CH3:4])[CH3:3].[OH-].[Li+].Cl>O1CCCC1.O>[CH2:1]([N:5]([C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:31])[F:32])[CH:27]=[CH:26][C:25]=1[CH3:34])[S:6]([C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([CH3:22])([CH3:23])[C:17]([OH:19])=[O:18])=[CH:13][CH:14]=1)(=[O:7])=[O:8])[CH:2]([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 86731596HCID 86731596, compound

Product 1

HCID 71543455HCID 71543455, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

To a stirred solution of ethyl 3-(4-(N-isobutyl-N-(2-methyl-5-(trifluoromethyl)phenyl)sulfamoyl)phenyl)-2,2-dimethylpropanoate (15 mg, 0.030 mmol) in tetrahydrofuran (THF) (1.5 mL), at room temperature, was added a solution of lithium hydroxide (approximately 0.719 mg, 0.030 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 evaporated in vacuo, then partitioned between water (2 mL) and ethyl acetate (2×5 mL). The organic fraction was separated (hydrophilic frit) and evaporated in vacuo to give a residue. This was redissolved in THF (1 mL) and water (1 mL) and new lithium hydroxide (tip of spatula) was added. The reaction was stood for 3 days, after which time the solvents had evaporated to give a white residue. The residue was acidified (2N HCl, 3 mL) and extracted with ethyl acetate (2×5 mL). The organics were separated (hydrophilic frit) and concentrated in vacuo, then purified by MDAP (Method F) to give the required product, 2.38 mg. LCMS (M+1) 472, RT 1.37 mins.

Workup

  1. waitstood overnight
  2. customThe mixture was evaporated in vacuo
  3. custompartitioned between water (2 mL) and ethyl acetate (2×5 mL)
  4. customThe organic fraction was separated (hydrophilic frit)
  5. customevaporated in vacuo
  6. customto give a residue
  7. waitThe reaction was stood for 3 days
  8. customafter which time the solvents had evaporated
  9. customto give a white residue
  10. extractionextracted with ethyl acetate (2×5 mL)
  11. customThe organics were separated (hydrophilic frit)
  12. concentrationconcentrated in vacuo
  13. custompurified by MDAP (Method F)

Sources & evidence

ORD record
ord-6920052898b94aee8f457e4fd8676902
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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