Lithium Hydroxide → HCID 68512729, compound

HRID 508124Notes

Reaction equation

HRID 508124 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][NH:5][C:6]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]2[CH2:22][C:21]([C:27]3[CH:32]=[C:31]([Cl:33])[CH:30]=[C:29]([Cl:34])[CH:28]=3)([C:23]([F:26])([F:25])[F:24])[O:20][N:19]=2)=[CH:10][CH:9]=1)=[O:7].[OH-].[Li+]>O1CCCC1.O>[Cl:34][C:29]1[CH:28]=[C:27]([C:21]2([C:23]([F:25])([F:24])[F:26])[O:20][N:19]=[C:18]([C:11]3[C:12]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:8]([C:6]([NH:5][CH2:4][C:3]([OH:35])=[O:2])=[O:7])=[CH:9][CH:10]=3)[CH2:22]2)[CH:32]=[C:31]([Cl:33])[CH:30]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68514950HCID 68514950, compound2×

Product 1

HCID 68512729HCID 68512729, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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 title product of Step A) (620 mg) in tetrahydrofuran (5 mL) was added an aqueous solution of lithium hydroxide (300 mg in 5 mL of water). 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, causing a white precipitate to form. The aqueous mixture was extracted with ethyl acetate, washed with brine, dried with anhydrous sodium sulfate, and concentrated to afford the title compound as a white solid (600 mg, 99% yield).

Workup

  1. extractionextracted with hexane
  2. customto form
  3. extractionThe aqueous mixture was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e83acbad591142879f4f6c24840061e9
Source dataset
uspto-grants-2015_08
Patent number
US09095138B2

Reaction notes

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