Lithium hydroxide, monohydrate → HCID 178461334, compound

HRID 1810059Notes

Reaction equation

HRID 1810059 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][S:5][C:6]1[S:10][C:9]([NH:11][C:12]([N:14]([CH2:22][C:23]([F:31])([F:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:15]2[CH2:20][CH2:19][CH:18]([CH3:21])[CH2:17][CH2:16]2)=[O:13])=[N:8][CH:7]=1.O[Li].O>C1COCC1.O>[F:31][C:23]([F:30])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:22][N:14]([C@H:15]1[CH2:16][CH2:17][C@H:18]([CH3:21])[CH2:19][CH2:20]1)[C:12](=[O:13])[NH:11][C:9]1[S:10][C:6]([S:5][CH2:4][C:3]([OH:32])=[O:2])=[CH:7][N:8]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86639125HCID 86639125, compound

Product 1

HCID 178461334HCID 178461334, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {2-[3-(2,2-difluoro-2-phenyl-ethyl)-3-(4-methyl-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid methyl ester (350 mg, 0.725 mmol) in THF (50 mL) was added LiOH.H2O (183 mg, 4.35 mmol) in water (3 mL) at RT. The mixture was stirred at RT for 16 h. Water was added and the mixture was extracted with dichloromethane. The organic layer was collected, dried over anhydrous sodium sulfate. The solvent was removed at reduced pressure and the residue was purified by preparative HPLC to give {2-[3-(2,2-difluoro-2-phenyl-ethyl)-3-(trans-4-methyl-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. customThe organic layer was collected
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed at reduced pressure
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-0f0f1bcd1f0a4a798fe712d54a502b45
Source dataset
uspto-grants-2013_01
Patent number
US08362049B2

Reaction notes

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