HCID 178427478, compound → HCID 178427477, compound

HRID 64829Notes

Reaction equation

HRID 64829 reaction equation
C([O:8][C:9](=[O:35])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:34])[C@H:16]([CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1)[NH:17][S:18]([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19])C1C=CC=CC=1>CO.C(OCC)(=O)C.[C].[Pd]>[S:18]([NH:17][C@H:16]([C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C:9]([OH:35])=[O:8])=[O:34])[CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1)([C:21]1[CH:22]=[CH:23][C:24]([CH3:25])=[CH:26][CH:27]=1)(=[O:19])=[O:20]

Participants

5

Reactant 1

HCID 178427478HCID 178427478, compound

Product 1

HCID 178427477HCID 178427477, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 150 ml of methanol was dissolved 13.5 g of compound (49) and the compound was catalytically reduced for 5 hours in the presence of 10% palladium-carbon. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue thus formed was dissolved in ethyl acetate and extracted thrice each time with an aqueous sodium hydrogen carbonate solution. The extracts were combined with each other and washed once with ethyl acetate. After acidifying the aqueous layer with 1N hydrochloric acid, the desired compound was extracted with ethyl acetate. Thus, 2.0 g of Nα -t-butyloxycarbonyl-Nim -tosyl-L-histidyl-L-proline (50) was obtained as a foamy product. Also, from the organic layer formed after extracting the product with an aqueous sodium hydrogencarbonate solution, 9.1 g of the starting material (49) was recovered.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue thus formed
  4. extractionextracted thrice each time with an aqueous sodium hydrogen carbonate solution
  5. washwashed once with ethyl acetate
  6. extractionthe desired compound was extracted with ethyl acetate

Sources & evidence

ORD record
ord-312530c2073a424489e6d30ff26f99aa
Source dataset
uspto-grants-1986_09
Patent number
US04610821

Reaction notes

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