Lithium hydroxide, monohydrate → HCID 71603338, compound

HRID 2363892Notes

Reaction equation

HRID 2363892 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]([C:22](=[O:32])[NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:30][CH3:31])[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]([C:22](=[O:32])[NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH3:31])[CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86686926HCID 86686926, compound

Product 1

HCID 71603338HCID 71603338, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {6-fluoro-4-[1-(2-methoxy-phenylcarbamoyl)-piperidin-4-yl]-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (107.6 mg, 0.232 mmol) in THF (8.0 mL) was added a solution of lithium hydroxide monohydrate (111.1 mg, 2.6 mmol) in water (2.0 mL) at room temperature. The resulting solution was stirred overnight at room temperature under a nitrogen atmosphere. The solvent was evaporated. Water (˜25 mL) was added and the mixture was acidified with 1.0 N aqueous HCl (4.6 mL). The resulting white precipitate was collected by filtration and dried under high vacuum to provide {6-fluoro-4-[1-(2-methoxy-phenylcarbamoyl)-piperidin-4-yl]-3-methyl-naphthalen-2-yl}-acetic acid (86.4 mg, 83%) as a white powder. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.45 (b. s, 1H), 7.90 (dd, J=9.23, 6.59 Hz, 1H), 7.78 (br. s., 1H), 7.65-7.72 (m, 2H), 7.35 (t, J=8.01 Hz, 1H), 6.99-7.06 (m, 2H), 6.86-6.95 (m, 1H), 4.23 (m, 2H), 3.82 (s, 3H), 3.78 (br. s., 2H), 3.32 (br. s., 3H), 3.09 (br. s., 2H), 2.43 (s, 3H), 1.66 (m, 2H). MS cald. for C26H28FN2O4 [(M+H)+]: 451, obsd. 451.2.

Workup

  1. customThe solvent was evaporated
  2. additionWater (˜25 mL) was added
  3. filtrationThe resulting white precipitate was collected by filtration
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-76fc7da35286494b8428cb2ad8b8933c
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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