Lithium hydroxide, monohydrate → HCID 68931117, compound

HRID 1027470Notes

Reaction equation

HRID 1027470 reaction equation
[CH3:1][C@@H:2]1[CH2:7][N:6]([C@@H:8]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:9]2[CH:14]=[CH:13][C:12]([C:15]#[C:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][N:3]1[CH2:29][C:30]([O:32]C(C)(C)C)=[O:31].O.[OH-].[Li+]>C1COCC1.CO.O>[CH3:1][C@@H:2]1[CH2:7][N:6]([C@@H:8]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:9]2[CH:10]=[CH:11][C:12]([C:15]#[C:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:13][CH:14]=2)[CH2:5][CH2:4][N:3]1[CH2:29][C:30]([OH:32])=[O:31]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68930450HCID 68930450, compound

Product 1

HCID 68931117HCID 68931117, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of tert-butyl 2-((R)-2-methyl-4-((S)-phenyl(4-(2-phenylethynyl)phenyl)-methyl)piperazin-1-yl)acetate (320 mg, 0.666 mmol) in THF/MeOH/H2O=5:5:1 (5.5 mL) was added lithium hydroxide monohydrate (279 mg, 6.658 mmol) and the resulting solution was stirred overnight. The solvent was evaporated to dryness under high vacuum and the residue was diluted with water, adjusted pH=5, extracted with DCM, dried over Na2SO4, filtered and evaporated to dryness. The residue was loaded onto flash column (SiO2, DCM to DCM/MeOH=100:5 to 100:10 to 100:15 to 100:20) to give 2-((R)-2-methyl-4-((S)-phenyl(4-(2-phenylethynyl)phenyl)methyl)piperazin-1-yl)acetic acid (240 mg) as a white solid.

Workup

  1. customThe solvent was evaporated to dryness under high vacuum
  2. additionthe residue was diluted with water, adjusted pH=5
  3. extractionextracted with DCM
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-3ba386ade2e74b2aa5ed98c2d312089c
Source dataset
uspto-grants-2014_05
Patent number
US08735383B2

Reaction notes

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