Lithium hydroxide, monohydrate → HCID 71603337, compound

HRID 2363890Notes

Reaction equation

HRID 2363890 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([CH:16]2[CH2:21][CH2:20][N:19]([C:22](=[O:31])[NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[CH2:18][CH2:17]2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:32])[CH:11]=2)[CH:6]=1.O.[OH-].[Li+]>C1COCC1.O>[Cl:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[NH:23][C:22]([N:19]1[CH2:18][CH2:17][CH:16]([C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([F:32])[CH:11]=3)[CH:6]=[C:5]([CH2:4][C:3]([OH:33])=[O:2])[C:14]=2[CH3:15])[CH2:21][CH2:20]1)=[O:31]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86686925HCID 86686925, compound

Product 1

HCID 71603337HCID 71603337, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {4-[1-(2-chloro-phenylcarbamoyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (10 mg, 0.021 mmol) in THF (2.0 mL) was added a solution of lithium hydroxide monohydrate (10.2 mg, 0.426 mmol) in water (0.5 mL) at room temperature. The resulting solution was stirred for 15 hours at room temperature under nitrogen atmosphere. The solvent was removed and the aqueous layer was neutralized with 1.0N HCl. The resulting white solids were collected by filtration, washed with water and hexanes, and dried in the air to give {4-[1-(2-chloro-phenylcarbamoyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid (4.5 mg, 46%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.42 (br. s, 1H), 7.9 (dd, J=8.91, 6.65 Hz, 1H), 7.69 (s, 1H), 7.48 (d, J=8.03 Hz, 2H), 7.25-7.42 (m, 3H), 7.09-7.23 (m, 1H), 4.27 (d, J=10.79 Hz, 2H), 3.79 (br. s, 4H), 2.43 (s, 4H), 1.65 (d, J=12.05 Hz, 3H), 1.23 (s, 2H). MS cald. for C25H25ClFN2O3 [(M+H)+] 455, obsd. 455.0.

Workup

  1. customThe solvent was removed
  2. filtrationThe resulting white solids were collected by filtration
  3. washwashed with water and hexanes
  4. customdried in the air

Sources & evidence

ORD record
ord-66df0c5e6e97452a8d85ac2a30699e7d
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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