Lithium hydroxide, monohydrate → HCID 71604045, compound

HRID 2363843Notes

Reaction equation

HRID 2363843 reaction equation
C[O:2][C:3](=[O:35])[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]=[CH:28][CH:27]=[C:26]([S:30]([CH3:33])(=[O:32])=[O:31])[CH:25]=3)(=[O:23])=[O:22])[CH2:17][CH2:16]2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:34])[CH:11]=2)[CH:6]=1.O.[OH-].[Li+]>C1COCC1.O>[F:34][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([CH2:4][C:3]([OH:35])=[O:2])[CH:14]=[C:13]2[CH:15]1[CH2:16][CH2:17][N:18]([S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([S:30]([CH3:33])(=[O:32])=[O:31])[CH:25]=2)(=[O:22])=[O:23])[CH2:19][CH2:20]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86686900HCID 86686900, compound

Product 1

HCID 71604045HCID 71604045, compoundYield 80.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of {6-fluoro-4-[1-(3-methanesulfonyl-benzenesulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (115 mg, 0.22 mmol) in THF (6 mL) was added a solution of lithium hydroxide monohydrate (46 mg, 1.1 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 {6-fluoro-4-[1-(3-methanesulfonyl-benzenesulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid (90 mg, 80%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.35 (br s, 1H), 8.34 (d, J=7.8 Hz, 1H), 8.23 (s, 1H), 8.18 (d, J=7.8 Hz, 1H), 7.98-8.04 (m, 1H), 7.95 (dd, J=9.3, 6.4 Hz, 1H), 7.86 (d, J=12.7 Hz, 1H), 7.69 (s, 1H), 7.35-7.41 (m, 2H), 3.87 (d, J=10.3 Hz, 2H), 3.71 (s, 2H), 3.39 (s, 3H), 2.66 (d, J=10.3 Hz, 2H), 1.89-1.96 (m, 2H), 1.73-1.83 (m, 1H); MS cald. for C24H25FNO6S2 [(M−H)−]: 506, obsd. 506.2.

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-8d67c3d1b94249cb98e7fb32ec97e264
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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