Lithium hydroxide, monohydrate → HCID 56961342, compound

HRID 1506895Notes

Reaction equation

HRID 1506895 reaction equation
O.[OH-].[Li+].[F:4][C:5]([F:31])([F:30])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH:15][C:16]1[S:20][C:19]2[CH2:21][CH2:22][CH2:23][CH2:24][C:18]=2[C:17]=1[C:25]([O:27]CC)=[O:26])(=[O:14])=[O:13]>O1CCOCC1.O>[F:30][C:5]([F:4])([F:31])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH:15][C:16]1[S:20][C:19]2[CH2:21][CH2:22][CH2:23][CH2:24][C:18]=2[C:17]=1[C:25]([OH:27])=[O:26])(=[O:14])=[O:13]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68278820HCID 68278820, compound2×

Product 1

HCID 56961342HCID 56961342, compoundYield 8.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Lithium hydroxide monohydrate (0.188 g) was added to a solution of ethyl 2-(2-trifluoromethylbenzenesulphonylamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (Intermediate 27, 0.194 g) in dioxane (1 ml) and water (1 ml) and the mixture was stirred at room temperature for 16 hours. The mixture was then warmed to 60° C. for 1 hour and finally heated in the microwave at 160° C. for 15 minutes. After cooling to room temperature the volatile components were removed under reduced pressure. The residual solution was acidified with aqueous hydrochloric acid (1M) and directly purified by preparative HPLC(C18), eluting with a mixture of methanol and water containing 0.1% formic acid and a gradient of 40-95% to give 2-(2-trifluoromethylbenzenesulphonylamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid (0.015 g) as a white solid.

Workup

  1. temperatureThe mixture was then warmed to 60° C. for 1 hour
  2. temperaturefinally heated in the microwave at 160° C. for 15 minutes
  3. temperatureAfter cooling to room temperature the volatile components
  4. customwere removed under reduced pressure
  5. customdirectly purified by preparative HPLC(C18)
  6. washeluting with a mixture of methanol and water containing 0.1% formic acid

Sources & evidence

ORD record
ord-acab2c95d2eb43beb02e2b8e6cec7b16
Source dataset
uspto-grants-2015_12
Patent number
US09221787B2

Reaction notes

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