Lithium hydroxide, monohydrate → HCID 46203588, compound

HRID 1644743Notes

Reaction equation

HRID 1644743 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:30])[CH:11]=2)[CH:6]=1.O.[OH-].[Li+]>O1CCCC1.O>[F:30][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([CH2:4][C:3]([OH:31])=[O:2])[C:14]([CH3:15])=[C:13]2[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([C:26]([F:28])([F:27])[F:29])(=[O:24])=[O:25])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59350809HCID 59350809, compound

Product 1

HCID 46203588HCID 46203588, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [6-fluoro-3-methyl-4-(4-trifluoromethanesulfonyl-benzyl)-naphthalen-2-yl]-acetic acid methyl ester (395 mg, 0.87 mmol) in tetrahydrofuran (15 mL) was added a solution of lithium hydroxide monohydrate (208 mg, 8.7 mmol) in water (3 mL) at room temperature. The resulting clear solution was stirred for 15 hours. Then, the tetrahydrofuran was removed under vacuum and the residue was diluted with water (10 mL). The aqueous solution was acidified with 1.0 N hydrochloric acid and the organic compound was extracted into ethyl acetate (2×20 mL). The combined organic extracts were washed with brine solution (50 mL) and dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the solvent under vacuum provided 343 mg (90%) of [6-fluoro-3-methyl-4-(4-trifluoromethanesulfonyl-benzyl)-naphthalen-2-yl]-acetic acid as a white solid. mp=200-201° C.: 1H NMR (300 MHz, DMSO-d6) δ ppm 12.45 (br. s, 1 H), 8.04 (d, J=8.4 Hz, 2 H), 7.96 (dd, J=9.1, 6.0 Hz, 1 H), 7.81 (s, 1 H), 7.69-7.80 (m, 1 H), 7.48 (d, J=8.4 Hz, 2 H), 7.29-7.43 (m, 1 H), 4.71 (s, 2 H), 3.84 (s, 2 H), 2.30 (s, 3 H). ES(+)-HRMS cald. for C21H16F4O4S [(M+Na)+] 463.0597, obsd. 463.0598.

Workup

  1. customThen, the tetrahydrofuran was removed under vacuum
  2. additionthe residue was diluted with water (10 mL)
  3. extractionthe organic compound was extracted into ethyl acetate (2×20 mL)
  4. washThe combined organic extracts were washed with brine solution (50 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationFiltration of the drying agent and concentration of the solvent under vacuum

Sources & evidence

ORD record
ord-3f021dfef3334ec7bdecacee21043069
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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