Lithium Hydroxide → HCID 68512729, compound

HRID 1958874Notes

Reaction equation

HRID 1958874 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:37])[CH2:6][NH:7][C:8]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:20]2[CH2:24][C:23]([C:29]3[CH:34]=[C:33]([Cl:35])[CH:32]=[C:31]([Cl:36])[CH:30]=3)([C:25]([F:28])([F:27])[F:26])[O:22][N:21]=2)=[CH:12][CH:11]=1)=[O:9]>O1CCCC1.O>[Cl:36][C:31]1[CH:30]=[C:29]([C:23]2([C:25]([F:27])([F:26])[F:28])[O:22][N:21]=[C:20]([C:13]3[C:14]4[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:10]([C:8]([NH:7][CH2:6][C:5]([OH:37])=[O:4])=[O:9])=[CH:11][CH:12]=3)[CH2:24]2)[CH:34]=[C:33]([Cl:35])[CH:32]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68514950HCID 68514950, compound2×

Product 1

HCID 68512729HCID 68512729, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

An aqueous solution of LiOH (300 mg, in 5 mL of H2O) was added to a stirred solution of N-[[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenyl]carbonyl]glycine methyl ester (i.e. the product of Step C, 620 mg) in tetrahydrofuran (5 mL). After stirring at room temperature for 1 h, the reaction mixture was diluted with water and extracted with hexane. The aqueous layer was acidified with 6.0 N HCl to pH 2, and a white precipitate formed. The aqueous mixture was extracted with ethyl acetate. The organic extract was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to provide the title compound (600 mg) as a white solid. 1H NMR (Me2S(O)-d6): δ 9.02 (t, 1H), 8.81 (d, 1H), 8.37 (d, 1H), 7.92 (d, 1H), 7.83 (t, 1H), 7.65-7.74 (m, 5H), 4.58 (d, 1H), 4.54 (d, 1H), 4.02 (d, 2H).

Workup

  1. extractionextracted with hexane
  2. customa white precipitate formed
  3. extractionThe aqueous mixture was extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-90a88703efd54ced8c90d93a0008339e
Source dataset
uspto-grants-2013_04
Patent number
US08410153B2

Reaction notes

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