Lithium hydroxide, monohydrate → HCID 46203918, compound

HRID 1644726Notes

Reaction equation

HRID 1644726 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][C:6]1[CH:15]=[C:14]([C:16](=[O:32])[C:17]2[CH:22]=[CH:21][C:20]([S:23]([N:26]3[CH2:31][CH2:30][NH:29][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:33])[CH:12]=2)[CH:7]=1)C.O.[OH-].[Li+]>O1CCCC1.O>[F:33][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH:7]=[C:6]([CH2:5][C:4]([OH:34])=[O:3])[CH:15]=[C:14]2[C:16](=[O:32])[C:17]1[CH:18]=[CH:19][C:20]([S:23]([N:26]2[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]2)(=[O:25])=[O:24])=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59350847HCID 59350847, compound

Product 1

HCID 46203918HCID 46203918, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of {6-fluoro-4-[4-(piperazine-1-sulfonyl)-benzoyl]-naphthalen-2-yl}-acetic acid ethyl ester (0.100 g, 0.17 mmol) in tetrahydrofuran (6 mL) was added a solution of lithium hydroxide monohydrate (0.035 g, 0.83 mmol) in water (1.5 mL) and the reaction mixture was stirred for 48 hours at room temperature. The reaction mixture was concentrated under reduced pressure, diluted with water (8 mL) and washed with ethyl acetate (2×5 mL). The aqueous layer was acidified with an aqueous solution of hydrochloric acid (1 N), then extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 0.050 g (52%) of {6-fluoro-4-[4-(piperazine-1-sulfonyl)-benzoyl]-naphthalen-2-yl}-acetic acid as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.13-8.17 (m, 1 H), 8.12 (s, 1 H), 7.99 (d, J=8.0 Hz, 2 H), 7.93-7.98 (m, 1 H), 7.89 (d, J=8.0 Hz, 2 H), 7.67 (s, 1 H), 7.57 (td, J=8.6, 2.0 Hz, 1 H), 3.76 (s, 2 H), 2.89 (br. s, 4 H), 2.76 (br. s, 4 H). MS cald. for C23H21FN2O5S [M+] 456, obsd. 456.9.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with water (8 mL)
  3. washwashed with ethyl acetate (2×5 mL)
  4. extractionextracted with ethyl acetate (3×10 mL)
  5. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-27d4ad3cce664473ae516b4c59465970
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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