HCID 86757990, compound → HCID 69950365, compound

HRID 843744Notes

Reaction equation

HRID 843744 reaction equation
C([O:8][C:9](=[O:51])[CH2:10][C@@H:11]([C:38]([NH:40][CH2:41][CH2:42][C:43]1[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=1)=[O:39])[NH:12]C([C@@H]1CCCN(C(=O)CCC2CCN(C(OC(C)(C)C)=O)CC2)C1)=O)C1C=CC=CC=1>C(O)(=O)C.[Pd]>[CH3:50][O:49][C:46]1[CH:45]=[CH:44][C:43]([CH2:42][CH2:41][NH:40][C:38]([C@H:11]([CH2:10][C:9]([OH:51])=[O:8])[NH2:12])=[O:39])=[CH:48][CH:47]=1

Participants

4

Reactant 1

HCID 86757990HCID 86757990, compound

Product 1

HCID 69950365HCID 69950365, compoundYield 233%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of N-[(R)-1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-3(S)-(4-methoxyphenethylamino)carbonyl-β-alanine benzyl ester (0.9 g) and 10% Pd—C (0.2 g, 50% wet) in acetic acid (10 ml) was hydrogenated at atmospheric pressure for 3 hours. After the catalyst was removed by filtration, the filtrate was concentrated in vacuo. The residue was poured into water and extract with ethyl acetate. The extract washed with water, brine and dried over MgSO4, and evaporated in vacuo. To give N-[(R)-1-{3-(1-tert-butoxycarbonyl)-4-piperidyl)propionyl}-3-piperidylcarbonyl]-3(S)-(4-methoxyphenethylamino)carbonyl-β-alanine as an oil (0.79 g).

Workup

  1. customAfter the catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionThe residue was poured into water
  4. extractionextract with ethyl acetate
  5. washThe extract washed with water, brine
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-067b6238ae2748e6ba4f20e6a9bc0e9b
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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