Lithium hydroxide, monohydrate → HCID 22275143, compound

HRID 1063990Notes

Reaction equation

HRID 1063990 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]([N:17]([S:26]([C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)(=[O:28])=[O:27])[C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[F:25])[CH3:16])C.O[Li].O>C1COCC1.CO.O>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([S:26]([N:17]([CH:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:36])=[O:3])[CH3:16])[C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])(=[O:27])=[O:28])=[CH:34][CH:33]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22275695HCID 22275695, compound

Product 1

HCID 22275143HCID 22275143, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl-4-[2-(1-{[(4-chlorophenyl)sulfonyl]-2,5-difluoroanilino}ethyl)phenoxy]butanoate (1.16 g, 2.2 mmol) in THF (5.2 mL), methanol (1.7 mL) and H2O (1.7 mL) was treated with LiOH.H2O (91 mg, 2.2 mmol) at 25° C. for 3 h. The reaction was then quenched with 1 N HCl solution. The aqueous phase was extracted with ethyl acetate. The combined organic phase was washed with H2O and sat. NaCl aqueous solution, then dried over MgSO4. Concentration and chromatography afforded the desired product (457 mg, 41%) as white crystal: m.p. 141.0-142.0° C.; Rf 0.14 (10:10, hexane-ethyl acetate); 1H NMR (CDCl3, 300 MHz) δ 11.08 (br s, 1H), 7.62 (d, 2H, J=8.4 Hz), 7.35 (d, 2H, J=8.7 Hz), 7.16 (t, 1H, J=7.5 Hz), 6.38-6.93 (m, 6H), 6.03 (br s, 1H), 4.06 (m, 2H), 2.70 (t, 2H, J=7.0 Hz), 2.17 (m, 2H), 1.57 (d, 3H, J=6.9 Hz); LCMS 3.05 min, m/z 527.2 (C24H22ClF2NO5S requires 509.95).

Workup

  1. customThe reaction was then quenched with 1 N HCl solution
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washThe combined organic phase was washed with H2O and sat. NaCl aqueous solution
  4. dry with materialdried over MgSO4
  5. concentrationConcentration and chromatography

Sources & evidence

ORD record
ord-37636f9eeb6d4222bcc6ad14fd5bcdac
Source dataset
uspto-grants-2005_11
Patent number
US06967196B1

Reaction notes

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