Lithium hydroxide, monohydrate → HCID 71604241, compound

HRID 2363879Notes

Reaction equation

HRID 2363879 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]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[NH2:32])(=[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>[NH2:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][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:33])[CH:11]=3)[CH:6]=[C:5]([CH2:4][C:3]([OH:34])=[O:2])[C:14]=2[CH3:15])[CH2:17][CH2:18]1)(=[O:24])=[O:23]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86686919HCID 86686919, compound

Product 1

HCID 71604241HCID 71604241, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {4-[1-(2-amino-phenylmethanesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (178 mg, 0.367 mmol) in THF 8.0 mL) was added a solution of lithium hydroxide monohydrate (176 mg, 7.35 mmol) in water (2.0 mL) at room temperature. The resulting solution was stirred for 15 hours under nitrogen. The solvent was removed under vacuum and the aqueous solution was diluted with water and slowly neutralized with 1.0 N HCl until the pH was between 5 and 6. The resulting precipitated solids were collected by filtration and washed with water and hexanes. After drying in the air, {4-[1-(2-amino-phenylmethane-sulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid (159 mg, 92%) was isolated as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 12.44 (br. s, 1H), 7.86 (dd, J=8.85, 6.59 Hz, 1H), 7.61 (s, 1H), 7.31 (t, J=7.91 Hz, 1H), 7.18 (d, J=7.35 Hz, 1H), 6.99-7.12 (m, 2H), 6.68-6.78 (m, 1H), 6.53-6.67 (m, 1H), 5.14 (br. s, 2H), 4.28-4.51 (m, 4H), 3.76 (d, J=10.93 Hz, 2H), 3.61 (br. s, 5H), 2.41 (br. s, 3H), 1.66 (d, J=11.49 Hz, 2H). MS cald. for C25H26FN2O4S [(M−H)−] 469, obsd. 469.1.

Workup

  1. customThe solvent was removed under vacuum
  2. additionthe aqueous solution was diluted with water and slowly neutralized with 1.0 N HCl until the pH was between 5 and 6
  3. customThe resulting precipitated solids
  4. filtrationwere collected by filtration
  5. washwashed with water and hexanes
  6. customAfter drying in the air

Sources & evidence

ORD record
ord-dd04cf8ba9a44b93a932fe2c367509db
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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