Lithium hydroxide, monohydrate → HCID 71604108, compound

HRID 2363845Notes

Reaction equation

HRID 2363845 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][C:5]1[CH:14]=[C:13]([CH:15]2[CH2:20][CH2:19][N:18]([S:21]([C:24]3[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=3[Cl:31])(=[O:23])=[O:22])[CH2:17][CH2:16]2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:32])[CH:11]=2)[CH:6]=1.O.[OH-].[Li+]>C1COCC1.O>[Cl:31][C:25]1[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:24]=1[S:21]([N:18]1[CH2:19][CH2:20][CH:15]([C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([F:32])[CH:11]=3)[CH:6]=[C:5]([CH2:4][C:3]([OH:33])=[O:2])[CH:14]=2)[CH2:16][CH2:17]1)(=[O:23])=[O:22]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86686901HCID 86686901, compound

Product 1

HCID 71604108HCID 71604108, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of {4-[1-(2,5-dichloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-naphthalen-2-yl}-acetic acid methyl ester (120 mg, 0.24 mmol) in THF (6 mL) was added a solution of lithium hydroxide monohydrate (50 mg, 1.2 mmol) in water (1.5 mL) and the reaction mixture was stirred for 24 h at RT. The reaction mixture was concentrated under reduced pressure and washed with diethyl ether (3×5 mL). The washings were discarded. Water (5 mL) was added to the residue, and the mixture acidified (pH ˜2-3) with an aqueous solution of hydrochloric acid (2 N) and extracted with ethyl acetate (3×5 mL). The combined organic extracts were dried over Na2SO4 and evaporated under reduced pressure to give {4-[1-(2,5-dichloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-naphthalen-2-yl}-acetic acid (105 mg, 90%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.38 (br s, 1H), 7.96-8.01 (m, 2H), 7.94 (d, J=4.4 Hz, 1H), 7.80-7.83 (m, 2H), 7.69 (s, 1H), 7.41 (t, J=8.8 Hz, 1H), 7.36 (s, 1H), 3.91 (d, J=12.2 Hz, 2H), 3.72 (s, 2H), 3.08 (t, J=11.5 Hz, 2H), 1.90-1.96 (m, 2H), 1.67-1.77 (m, 2H); MS cald. for C23H19Cl2FNO4S [(M−H)−]: 494, obsd. 494.3.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washwashed with diethyl ether (3×5 mL)
  3. additionWater (5 mL) was added to the residue
  4. extractionextracted with ethyl acetate (3×5 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-97d5b7b719b74aa584d3a3dad4a5ed66
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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