HCID 46633065, compound → HCID 28505590, compound

HRID 1061658Notes

Reaction equation

HRID 1061658 reaction equation
C(OC([NH:11][C@@H:12]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)=[O:14])=O)C1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:11][C@@H:12]([CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:17][CH2:16]1)=[O:14]

Participants

4

Reactant 1

HCID 46633065HCID 46633065, compound

Product 1

HCID 28505590HCID 28505590, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of (2S)-2-(benzyloxycarbonyl)amino-1-{4-(tert-butoxycarbonyl)piperazin-1-yl}-3-phenyl-1-propanone (4.2 g, Reference compound No. 25-1) in ethanol (30 ml) is saturated with a nitrogen gas. Then, 5% palladium hydroxide/carbon (2.1 g) is added to the solution, and the whole is stirred overnight under a hydrogen atmosphere (4.2 kgf/cm−1). The reaction mixture is filtered to remove the catalyst. The filtrate is concentrated under reduced pressure, ethyl acetate is added to the resulting residue, and the whole is extracted with a 10% aqueous citric acid solution. Sodium hydrogencarbonate is added to the extract to basify the system, and the whole is extracted with ethyl acetate. The extract is dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the titled reference compound (1.32 g).

Workup

  1. filtrationThe reaction mixture is filtered
  2. customto remove the catalyst
  3. concentrationThe filtrate is concentrated under reduced pressure, ethyl acetate
  4. additionis added to the resulting residue
  5. extractionthe whole is extracted with a 10% aqueous citric acid solution
  6. additionSodium hydrogencarbonate is added to the
  7. extractionextract
  8. extractionthe whole is extracted with ethyl acetate
  9. dry with materialThe extract is dried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ab2d20d1a53a4a05b80cfe848a550cd7
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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