Hydrochloric Acid → 3-(3-Tert-butoxycarbonyl-propane-1-sulfonyl)-5-trifluoromethyl-benzoic acid

HRID 403389Notes

Reaction equation

HRID 403389 reaction equation
C[O:2][C:3](=[O:27])[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([S:14]([CH2:17][CH2:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])(=[O:16])=[O:15])[CH:5]=1.O.O.[OH-].[Li+].Cl>O1CCOCC1>[C:23]([O:22][C:20]([CH2:19][CH2:18][CH2:17][S:14]([C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([C:10]([F:13])([F:11])[F:12])[CH:7]=1)[C:3]([OH:27])=[O:2])(=[O:15])=[O:16])=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 682038303-(3-Tert-butoxycarbonyl-propane-1-sulfonyl)-5-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 682038293-(3-Tert-butoxycarbonyl-propane-1-sulfonyl)-5-trifluoromethyl-benzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-(3-tert-butoxycarbonyl-propane-1-sulfonyl)-5-trifluoromethyl-benzoic acid methyl ester (100 mg, 0.244 mmol) in dioxane (1 mL) was added water (1 mL) and lithiumhydroxide monohydrate (11.2 mg, 0.268 mmol) and the resulting suspension stirred at room temperature for 4 hours. The reaction mixture was acidified with 1M aqueous hydrochloric acid and extracted with EtOAc (30 mL) and the layers were separated. The aqueous layer was extracted a second time with EtOAc (30 mL). The organic layers were washed with brine (30 mL), dried over magnesium sulfate, filtered and concentrated under vacuum. Colorless solid (76 mg, 78.7%). MS (ESI−): m/z=395.08 ([M−H]−).

Workup

  1. extractionextracted with EtOAc (30 mL)
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted a second time with EtOAc (30 mL)
  4. washThe organic layers were washed with brine (30 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-39e6a454549243eb86cbd92d39b5acf7
Source dataset
uspto-grants-2014_06
Patent number
US08748434B2

Reaction notes

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