Hydrochloric Acid → HCID 178501218, compound

HRID 926035Notes

Reaction equation

HRID 926035 reaction equation
[CH:1]([N:4]([C@H:23]1[CH2:28][CH2:27][C@H:26]([C:29]([O:31][CH3:32])=[O:30])[CH2:25][CH2:24]1)[S:5]([C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=1)[C:11]([O:13]CC[Si](C)(C)C)=[O:12])(=[O:7])=[O:6])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].Cl>C1COCC1>[CH:1]([N:4]([C@H:23]1[CH2:28][CH2:27][C@H:26]([C:29]([O:31][CH3:32])=[O:30])[CH2:25][CH2:24]1)[S:5]([C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=1)[C:11]([OH:13])=[O:12])(=[O:7])=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 178501219HCID 178501219, compound

Product 1

HCID 178501218HCID 178501218, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 305 mg of 2-(trimethylsilyl)ethyl 3-{isopropyl[trans-4-(methoxycarbonyl)cyclohexyl]sulfamoyl}benzoate, a solution of TBAF in THF (1.0 M, 1.0 mL), and 3.0 mL of THF was stirred at room temperature for 2 hours. To the reaction mixture was added 0.2 M hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with 0.2 M hydrochloric acid, water, and saturated brine in this order, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 240 mg of 3-{isopropyl[trans-4-(methoxycarbonyl)cyclohexyl]sulfamoyl}benzoic acid as a colorless oil.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with 0.2 M hydrochloric acid, water, and saturated brine in this order
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7061f9e68ba047b2a120bf2750b56e87
Source dataset
uspto-grants-2016_03
Patent number
US09284295B2

Reaction notes

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