Lithium Hydroxide → HCID 57565215, compound

HRID 1727059Notes

Reaction equation

HRID 1727059 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][C:6]1[C:7]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([S:17]([N:20]3[CH2:25][CH2:24][N:23]([C:26]4[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][N:27]=4)[CH2:22][CH2:21]3)(=[O:19])=[O:18])[C:8]=2[S:9][CH:10]=1)C.[Li+].[OH-].FC(F)(F)C1C=CC(C2CCNCC=2)=CC=1>C1COCC1.CO>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:7]2[C:6]([CH2:5][C:4]([OH:36])=[O:3])=[CH:10][S:9][C:8]=2[C:11]=1[S:17]([N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][N:27]=2)[CH2:22][CH2:21]1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 12440708Pyridine, 1,2,3,6-tetrahydro-4-[4-(trifluoromethyl)phenyl]-HCID 57565241{6-Methoxy-7-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazine-1-sulfonyl]-benzo[b]thiophen-3-yl}-acetic acid ethyl ester

Product 1

HCID 57565215HCID 57565215, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Compound from step 4 (22 mg, 0.041 mmol) was dissolved in 2 mL of THF/MeOH (3:1), followed by addition of 1N LiOH (5.0 eqv). The resulting mixture were stirred at 40° C. for 3 hours. The organic solvent was evaporated under N2 and residues were diluted with water (2 mL). The aqueous layers were partitioned with ether (2 mL). After removal of organic layers, the aqueous layers were neutralized by 1N HCl (5.0 eqv) and then extracted with ethyl acetate (5 mL). The organic layers were washed with H2O, brine, and dried over Na2SO4. The solution was concentrated in vacuo to afford {6-Methoxy-7-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazine-1-sulfonyl]-benzo[b]thiophen-3-yl}-acetic acid. 1H NMR (400 MHz, CDCl3) δ 8.32 (s, 1H), 8.38 (s, 1H), 7.78 (d, 1H), 7.61 (d, 1H), 7.22 (s, 1H), 6.60 (m, 1H), 4.01 (s, 2H), 3.98 (s, 3H), 3.77 (m, 4H), 3.22 (m, 4H).

Workup

  1. customThe organic solvent was evaporated under N2
  2. additionresidues were diluted with water (2 mL)
  3. customThe aqueous layers were partitioned with ether (2 mL)
  4. customAfter removal of organic layers
  5. extractionextracted with ethyl acetate (5 mL)
  6. washThe organic layers were washed with H2O, brine
  7. dry with materialdried over Na2SO4
  8. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-b4b45682d14345d2969b2c02a0da9f3b
Source dataset
uspto-grants-2009_02
Patent number
US07494999B2

Reaction notes

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