Lithium hydroxide, monohydrate → HCID 46202302, compound

HRID 1644730Notes

Reaction equation

HRID 1644730 reaction equation
C([O:3][C:4](=[O:35])[CH2:5][C:6]1[CH:15]=[C:14]([C:16](=[O:33])[C:17]2[CH:22]=[CH:21][C:20]([S:23]([N:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)(=[O:25])=[O:24])=[CH:19][CH:18]=2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:34])[CH:12]=2)[CH:7]=1)C.O.[OH-].[Li+]>O1CCCC1.O>[F:34][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH:7]=[C:6]([CH2:5][C:4]([OH:35])=[O:3])[CH:15]=[C:14]2[C:16](=[O:33])[C:17]1[CH:18]=[CH:19][C:20]([S:23]([N:26]2[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH2:31]2)(=[O:25])=[O:24])=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59350823HCID 59350823, compound

Product 1

HCID 46202302HCID 46202302, compoundYield 42.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of {6-fluoro-4-[4-(4-methyl-piperazine-1-sulfonyl)-benzoyl]-naphthalen-2-yl}-acetic acid ethyl ester (0.05 g, 0.10 mmol) in tetrahydrofuran (6 mL) was added a solution of lithium hydroxide monohydrate (0.021 g, 0.50 mmol) in water (1.5 mL) and the reaction mixture was stirred for 48 hours at room temperature. The solvents were distilled off under reduced pressure, then the residue was diluted with water (4 mL) and washed with ethyl acetate (2×3 mL) to remove unwanted organic products. The aqueous layer was separated and acidified to pH ˜3-4 with a 1.0 N aqueous solution of hydrochloric acid. The resulting mixture was extracted with ethyl acetate (2×10 mL). The combined organic phases were dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield 0.020 g (42%) of {6-fluoro-4-[4-(4-methyl-piperazine-1-sulfonyl)-benzoyl]-naphthalen-2-yl}-acetic acid as white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.09-8.19 (m, 2 H), 7.84-8.05 (m, 5 H), 7.71 (s, 1 H), 7.48-7.61 (m, 1 H), 3.81 (s, 2 H), 2.97 (br. s, 4 H), 2.38 (br. s, 4 H), 2.15 (s, 3 H). MS cald. for C24H23FN2O5S ([M+H]+) 471, obsd. 471.3.

Workup

  1. distillationThe solvents were distilled off under reduced pressure
  2. additionthe residue was diluted with water (4 mL)
  3. washwashed with ethyl acetate (2×3 mL)
  4. customto remove unwanted organic products
  5. customThe aqueous layer was separated
  6. extractionThe resulting mixture was extracted with ethyl acetate (2×10 mL)
  7. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fe60ed755c3b4dccb54b403d0791c4c6
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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