Lithium hydroxide, monohydrate → HCID 71604112, compound

HRID 2363853Notes

Reaction equation

HRID 2363853 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]([S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:31])(=[O:24])=[O:23])[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:31][C:26]1[CH:27]=[CH:28][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:32])[CH:11]=3)[CH:6]=[C:5]([CH2:4][C:3]([OH:33])=[O:2])[C:14]=2[CH3:15])[CH2:17][CH2:18]1)(=[O:23])=[O:24]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86686905HCID 86686905, compound

Product 1

HCID 71604112HCID 71604112, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a clear, almost colorless solution of {4-[1-(2-chloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (108 mg, 0.23 mmol) in THF (8.0 mL) was added a solution of lithium hydroxide monohydrate (106 mg, 4.4 mmol) in water (2.0 mL) The mixture was heated with a heat gun to give a clear solution. The resulting solution was stirred for 15 hours at room temperature. The solvent was removed under vacuum. The residue was diluted with water (˜20 mL) and the mixture was neutralized with 1.0 N HCl. The precipitated white solids were collected by filtration and washed with water and hexanes. After air drying, {4-[1-(2-chloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid (93 mg, 87%) was isolated as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.42 (br. s, 1H), 8.07 (d, J=7.53 Hz, 2H), 783-7.96 (m, 1H), 7.65-7.82 (m, 3H), 7.56-7.64 (m, 1H), 7.28-7.40 (m, 1H), 3.91 (d, J=11.29 Hz, 4H), 3.76 (br. s, 3H), 3.05 (br. s, 2H), 2.36 (s, 3H), 1.68 (d, J=12.3 Hz, 2H). MS cald. for C24H24ClFNO4S [(M+H)+] 476, obsd. 476.1.

Workup

  1. temperaturewas heated with a heat gun
  2. customto give a clear solution
  3. customThe solvent was removed under vacuum
  4. additionThe residue was diluted with water (˜20 mL)
  5. filtrationThe precipitated white solids were collected by filtration
  6. washwashed with water and hexanes
  7. customAfter air drying

Sources & evidence

ORD record
ord-09c51a2c778c4197a02c5cffa19737c8
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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