Lithium hydroxide, monohydrate → HCID 178449566, compound

HRID 1881117Notes

Reaction equation

HRID 1881117 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]([CH:25]2[CH2:30][CH2:29][CH:28]([CH3:31])[CH2:27][CH2:26]2)[CH2:15][C:16]([CH3:24])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:17])=[O:13])=[N:8][CH:7]=1.O[Li].O>C1COCC1.O>[CH3:31][C@H:28]1[CH2:29][CH2:30][C@H:25]([N:14]([CH2:15][C:16]([CH3:24])([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH3:17])[C:12](=[O:13])[NH:11][C:9]2[S:10][C:6]([S:5][CH2:4][C:3]([OH:32])=[O:2])=[CH:7][N:8]=2)[CH2:26][CH2:27]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86639124HCID 86639124, compound

Product 1

HCID 178449566HCID 178449566, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {2-[3-(4-methyl-cyclohexyl)-3-(2-methyl-2-phenyl-propyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid methyl ester (350 mg, 0.737 mmol) in THF(50 mL) was added LiOH.H2O (186 mg, 4.42 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-(trans-4-Methyl-cyclohexyl)-3-(2-methyl-2-phenyl-propyl)-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-bbedcc632f464472a10b60f3aa1f6008
Source dataset
uspto-grants-2012_11
Patent number
US08318778B2

Reaction notes

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