Hydrochloric Acid → HCID 18659596, compound

HRID 1608511Notes

Reaction equation

HRID 1608511 reaction equation
[I-].Br[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:9]([CH:11]([NH:16][C:17](=[O:34])[C@H:18]([CH2:30][CH:31]([CH3:33])[CH3:32])[NH:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[CH2:12][CH2:13][CH2:14][CH3:15])=[O:10].Cl>C1COCC1.C1C=CC=CC=1.[Zn]>[OH:10][CH:9]([CH:11]([NH:16][C:17](=[O:34])[C@H:18]([CH2:30][CH:31]([CH3:33])[CH3:32])[NH:19][C:20]([O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:21])[CH2:12][CH2:13][CH2:14][CH3:15])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 30165Iodide IonHCID 455774117591-20-5

Product 1

HCID 18659596HCID 18659596, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 10 ml of anhydrous THF were added 360 mg of zinc powder and a small amount of iodide, and the mixture was heated at reflux. A solution of 0.54 ml of ethyl bromoacetate in 6.0 ml of anhydrous THF was added thereto dropwise, followed by heating at reflux for 5 minutes. A solution of 1.0 g of N-benzyloxycarbonyl-L-leucine-(1-formyl)pentylamide prepared in the same manner as in Example 4-(b) in 14 ml of anhydrous benzene was then added thereto dropwise, followed by heating at reflux for 30 minutes. After allowing the mixture to cool, 1N hydrochloric acid was added thereto, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was purified by medium-pressure column chromatography on silica gel to obtain 410 mg of the titled compound as an oily substance.

Workup

  1. temperatureat reflux
  2. temperatureby heating
  3. temperatureat reflux for 5 minutes
  4. additionwas then added
  5. temperatureby heating
  6. temperatureat reflux for 30 minutes
  7. temperatureto cool
  8. extractionthe reaction mixture was extracted with ethyl acetate
  9. washThe organic layer was washed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was removed by distillation under reduced pressure
  12. customthe residue was purified by medium-pressure column chromatography on silica gel

Sources & evidence

ORD record
ord-2a013cd635e2427cb261b528d896da7e
Source dataset
uspto-grants-1995_03
Patent number
US05395824

Reaction notes

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