Hydrochloric Acid → HCID 15462778, compound

HRID 1420785Notes

Reaction equation

HRID 1420785 reaction equation
[CH3:1][O:2][C:3](=[O:33])[C:4]([N:19]=C(C1C=CC=CC=1)C1C=CC=CC=1)([CH2:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1.Cl>C1COCC1>[CH3:1][O:2][C:3](=[O:33])[C:4]([NH2:19])([CH2:5][C:6]1[CH:7]=[CH:8][N:9]=[CH:10][CH:11]=1)[CH2:12][C:13]1[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 541067012-Benzhydrylideneamino-3-pyridin-4-yl-2-pyridin-4-ylmethyl-propionic acid methyl ester

Product 1

HCID 15462778HCID 15462778, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Benzhydrylideneamino-3-pyridin-4-yl-2-pyridin-4-ylmethyl-propionic acid methyl ester (49.6 g, 113 mmol) was dissolved in anhydrous THF (640 ml). To the reaction was added 227 ml of a solution of 2.0 M aqueous hydrochloric acid (HCl). The mixture was stirred at ambient temperature for one hour. The reaction was subsequently concentrated under vacuum to remove the THF. The reaction was then partitioned between ethyl ether and water. The aqueous layer was washed two more times with ethyl ether. The pH of the aqueous layer was then adjusted to 9 with sodium carbonate (Na2CO3) and the solution is extracted with methylene chloride until virtually no product is left in the methylene chloride (CH2Cl2) layer. The CH2Cl2 extracts were combined, dried over Na2SO4, filtered and concentrated under vacuum to give 25.6 g (94.4 mmol) of the titled compound as a yellow solid.

Workup

  1. concentrationThe reaction was subsequently concentrated under vacuum
  2. customto remove the THF
  3. customThe reaction was then partitioned between ethyl ether and water
  4. washThe aqueous layer was washed two more times with ethyl ether
  5. extractionthe solution is extracted with methylene chloride until virtually no product
  6. waitis left in the methylene chloride (CH2Cl2) layer
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7a5576927ce548288d0dfe43a646c38e
Source dataset
uspto-grants-2000_06
Patent number
US06071935

Reaction notes

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