Lithium hydroxide, monohydrate → HCID 86686912, compound

HRID 2363865Notes

Reaction equation

HRID 2363865 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][CH:28]=[CH:27][C:26]=3[O:31][CH3:32])(=[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.O.[OH-].[Li+]>C1COCC1.O>[F:33][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([CH2:4][C:3]([OH:34])=[O:2])[C:14]([CH3:15])=[C:13]2[CH:16]1[CH2:21][CH2:20][N:19]([S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])(=[O:24])=[O:23])[CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86686911HCID 86686911, compound

Product 1

HCID 86686912HCID 86686912, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {6-fluoro-4-[1-(2-methoxy-benzenesulfonyl)-piperidin-4-yl]-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (64 mg, 0.132 mmol) in THF (8.0 mL) was added a solution of lithium hydroxide monohydrate (63.3 mg, 1.5 mmol) in water (2 mL). The reaction mixture was stirred at room temperature overnight under nitrogen. After this time, the reaction mixture was concentrated. Water (˜20 mL) was added and the mixture was acidified with 1.0 N aqueous HCl (2.7 mL). The resulting white precipitate was collected by vacuum filtration, washed with hexanes, and then further dried under vacuum to provide {6-fluoro-4-[1-(2-methoxy-benzenesulfonyl)-piperidin-4-yl]-3-methyl-naphthalen-2-yl}-acetic acid (51.5 mg, 83%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.45 (br. s, 1H), 8.04 (br. s, 1H), 7.85-7.92 (m, 1H), 7.78-7.84 (m, 1H), 7.67 (s, 2H), 7.29-7.37 (m, 2H), 7.13 (t, J=8.00 Hz, 1H), 3.94 (s, 3H), 3.82-3.92 (m, 2H), 3.70-3.80 (m, 2H), 2.82-3.02 (m, 2H), 2.35 (s, 3H), 2.13-2.32 (m, 1H), 1.60-1.71 (m, 2H). MS cald. for C25H27FNO5S [(M+H)+]: 472, obsd. 472.2.

Workup

  1. concentrationAfter this time, the reaction mixture was concentrated
  2. additionWater (˜20 mL) was added
  3. filtrationThe resulting white precipitate was collected by vacuum filtration
  4. washwashed with hexanes
  5. customfurther dried under vacuum

Sources & evidence

ORD record
ord-f595e46413e54d23afef604ffe327956
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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