Lithium Hydroxide → HCID 71604240, compound

HRID 2363877Notes

Reaction equation

HRID 2363877 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]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[N+:32]([O-:34])=[O:33])(=[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.[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]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N+:32]([O-:34])=[O:33])(=[O:23])=[O:24])[CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86686918HCID 86686918, compound

Product 1

HCID 71604240HCID 71604240, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a light yellow solution of {6-fluoro-3-methyl-4-[1-(2-nitro-phenylmethanesulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (100 mg, 0.194 mmol) in THF (4 mL) was added a solution of lithium hydroxide (93.1 mg, 3.89 mmol) in water (1 mL) at room temperature. The resulting light brown solution was stirred for 15 hours at room temperature. The THF was evaporated off under vacuum and the basic aqueous layer was neutralized with 1.0 N HCl. The resulting solids were filtered using filter paper and washed with water and hexanes. The white solid (82 mg) was dissolved in ethyl acetate (˜5 mL) with heating and the mixture was diluted with hexanes. During the dilution some precipitate was formed. Cooling in the refrigerator precipitated additional solids. {6-Fluoro-3-methyl-4-[1-(2-nitro-phenylmethanesulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid (88 mg, 90%) was isolated as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 12.44 (br. s, 1H), 8.08 (d, J=8.03 Hz, 1H), 7.90 (dd, J=8.91, 6.65 Hz, 1H), 7.74-7.86 (m, 3H), 7.64-7.73 (m, 2H), 7.36 (t, J=8.03 Hz, 1H), 4.97 (s, 2H), 3.52-3.90 (m, 7H), 2.42 (br. s, 3H), 1.60-184 (m, 4H). MS cald. for C25H25FN2O6S [(M+H)+] 500, obsd. 501.1.

Workup

  1. customThe THF was evaporated off under vacuum
  2. filtrationThe resulting solids were filtered
  3. filtrationusing filter paper
  4. washwashed with water and hexanes
  5. dissolutionThe white solid (82 mg) was dissolved in ethyl acetate (˜5 mL)
  6. temperaturewith heating
  7. additionthe mixture was diluted with hexanes
  8. customDuring the dilution some precipitate was formed
  9. temperatureCooling in the refrigerator
  10. customprecipitated additional solids

Sources & evidence

ORD record
ord-977eeb9514f5447582121962f1498318
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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