Hydrochloric Acid → HCID 10237363, compound

HRID 2245861Notes

Reaction equation

HRID 2245861 reaction equation
C[O:2][C:3](=[O:36])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C@@H:10]([N:25]2[CH2:30][C@@H:29]([CH3:31])[N:28]([CH2:32][CH:33]=[CH2:34])[CH2:27][C@@H:26]2[CH3:35])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][Si](C(C)(C)C)(C)C)[CH:12]=2)[CH:5]=1.[OH-].[Na+].Cl>C1COCC1>[CH2:32]([N:28]1[C@H:29]([CH3:31])[CH2:30][N:25]([C@@H:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)[C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:36])=[O:2])[C@@H:26]([CH3:35])[CH2:27]1)[CH:33]=[CH2:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68695687HCID 68695687, compound

Product 1

HCID 10237363HCID 10237363, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-{(R)-((2S,5R)-4-allyl-2,5-dimethyl-piperazin-1-yl)[3-(tert-butyl-dimethylsilanyloxy)phenyl]methyl}benzoic acid methyl ester (7.4 g, 14.5 mmol) and 18.2 mL of 2.0 N aqueous sodium hydroxide (36.4 mmol, 2.5 eq) in THF (30 mL) was stirred overnight at room temperature. Hydrochloric acid (18.2 mL of 2 N aqueous solution) was added, and the THF was removed under vacuum. The aqueous residue was filtered to collect precipitated solid, which was washed with dichloromethane to remove organic impurities. The aqueous filtrate was concentrated to dryness to give additional solid material. The recovered solids were combined, washed with water to remove sodium chloride, and dried to give 5.5 g (99.4%) of crude 3-[(R)-((2S,5R)-4-allyl-2,5-dimethylpiperazin-1-yl)(3-hydroxyphenyl)methyl]benzoic acid (Acid A).

Workup

  1. customthe THF was removed under vacuum
  2. filtrationThe aqueous residue was filtered
  3. customto collect
  4. customprecipitated solid, which
  5. washwas washed with dichloromethane
  6. customto remove organic impurities
  7. concentrationThe aqueous filtrate was concentrated to dryness
  8. customto give additional solid material
  9. washwashed with water
  10. customto remove sodium chloride
  11. customdried

Sources & evidence

ORD record
ord-fb09191751de4d34ae4fb78af5d1525e
Source dataset
uspto-grants-2010_03
Patent number
US07683168B2

Reaction notes

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