Lithium hydroxide, monohydrate → HCID 71604237, compound

HRID 2363871Notes

Reaction equation

HRID 2363871 reaction equation
C[O:2][C:3](=[O:36])[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]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=3)(=[O:24])=[O:23])[CH2:18][CH2:17]2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:35])[CH:11]=2)[CH:6]=1.O.[OH-].[Li+]>C1COCC1.O>[F:35][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([CH2:4][C:3]([OH:36])=[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]=[C:27]([C:31]([F:32])([F:34])[F:33])[CH:26]=2)(=[O:24])=[O:23])[CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86686915HCID 86686915, compound

Product 1

HCID 71604237HCID 71604237, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {6-fluoro-3-methyl-4-[1-(3-trifluoromethyl-benzenesulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (104.2 mg, 0.199 mmol) in THF (8.0 mL) was added a solution of lithium hydroxide monohydrate (95.3 mg, 2.3 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 (˜25 mL) was added and the mixture was acidified with 1.0 N aqueous HCl (4 mL). The resulting white precipitate was collected by vacuum filtration, washed with water and hexanes, and then further dried under vacuum to afford {6-fluoro-3-methyl-4-[1-(3-trifluoromethyl-benzenesulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid (92.2 mg, 91%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.43 (br. s, 1H), 8.18-8.20 (m, 1H), 8.16-8.18 (m, 1H), 8.07 (s, 1H), 7.97 (t, J=7.80 Hz, 1H), 7.84-7.91 (m, 1H), 7.67 (s, 1H), 7.33 (t, J=9.00 Hz, 1H), 3.92 (br. s., 2H), 3.74 (s, 2H), 3.41-3.70 (m, 2H), 2.57-2.84 (m, 2H), 2.31 (s, 3H), 2.40-2.28 (m, 1H), 1.69 (m, 2H). MS cald. for C25H22F4NO4S [(M−H)−]: 508, obsd. 508.1.

Workup

  1. concentrationAfter this time, the reaction mixture was concentrated
  2. additionWater (˜25 mL) was added
  3. filtrationThe resulting white precipitate was collected by vacuum filtration
  4. washwashed with water and hexanes
  5. customfurther dried under vacuum

Sources & evidence

ORD record
ord-f5a9884d589e4b3dadb0fdedf5e0b676
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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