Hydrochloric Acid → HCID 15713248, compound

HRID 847377Notes

Reaction equation

HRID 847377 reaction equation
Cl.C([N:4]1[CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:8][C:7](=[CH2:15])[CH2:6][CH:5]1[C:16]([O:18][CH2:19][CH3:20])=[O:17])=O>C(O)C>[CH2:15]=[C:7]1[CH2:6][CH:5]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:4][CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:8]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15713246HCID 15713246, compound

Product 1

HCID 15713248HCID 15713248, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.5 ml of 12N hydrochloric acid were added to a solution of 2.8 g of the product of Step C of Example 5 and 30 ml of ethanol and the reaction mixture was refluxed for 2 hours. After evaporation to dryness, the residue was taken up in ethyl acetate and washed with 10% sodium bicarbonate. The organic phase was dried, filtered and evaporated to dryness to obtain 2.0 g of product which was purified on silica eluting with a cyclohexane-ethyl acetate (8-2) mixture to obtain 0.730 g of the cis product and 0.980 g of the trans product.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 hours
  2. customAfter evaporation to dryness
  3. washwashed with 10% sodium bicarbonate
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-a0087a29053147d4b082a32e52073820
Source dataset
uspto-grants-1992_08
Patent number
US05141952

Reaction notes

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