Lithium Hydroxide → HCID 71604171, compound

HRID 2363857Notes

Reaction equation

HRID 2363857 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([CH:16]2[CH2:21][CH2:20][N:19]([S:22]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=3[Cl:32])(=[O:24])=[O:23])[CH2:18][CH2:17]2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:33])[CH:11]=2)[CH:6]=1.[OH-].[Li+]>C1COCC1.O>[Cl:32][C:26]1[CH:27]=[C:28]([Cl:31])[CH:29]=[CH:30][C:25]=1[S:22]([N:19]1[CH2:20][CH2:21][CH:16]([C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([F:33])[CH:11]=3)[CH:6]=[C:5]([CH2:4][C:3]([OH:34])=[O:2])[C:14]=2[CH3:15])[CH2:17][CH2:18]1)(=[O:24])=[O:23]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86686907HCID 86686907, compound

Product 1

HCID 71604171HCID 71604171, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a colorless solution of {4-[1-(2,4-dichloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (109 mg, 0.208 mmol) in THF (8.0 mL) was added a solution of an excess lithium hydroxide (100 mg, 4.18 mmol) in water (2.0 mL) at room temperature. The resulting light yellow solution was stirred for 15 hours. The reaction mixture was concentrated and the aqueous solution was diluted with water then neutralized with 1.0 N aqueous HCl. The resulting suspension was extracted into ethyl acetate (2×40 mL). The combined extracts were washed with brine and dried over anhydrous MgSO4, filtered, and concentrated to afford {4-[1-(2,4-dichloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid (105 mg, 99%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.32 (br. s, 1H), 8.06 (d, J=8.5 Hz, 1H), 7.98 (d, J=2.0 Hz, 1H), 7.88 (dd, J=8.5, 6.8 Hz, 1H), 7.64-7.82 (m, 3H), 7.25-7.39 (m, 1H), 3.82-3.94 (m, 2H), 3.76 (br. s, 2H), 3.47-3.72 (m, 1H), 3.07 (br. s, 2H), 2.36 (s, 3H), 2.09-2.46 (m, 2H), 1.68 (d, J=12.0 Hz, 2H). MS cald. for C24H23Cl2FNO4S [(M+H)+] 510, obsd. 510.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe aqueous solution was diluted with water
  3. extractionThe resulting suspension was extracted into ethyl acetate (2×40 mL)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2361286615684b08ad38c99a8bf3a7cb
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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