HCID 86588493, compound → HCID 9803820, compound

HRID 1862533Notes

Reaction equation

HRID 1862533 reaction equation
C([O:8][C:9](=[O:35])[C@@H:10]([NH:31][C:32](=[O:34])[CH3:33])[CH2:11][NH:12][C:13]([C@@H:15]1[CH2:20][CH2:19][CH2:18][N:17]([C:21](=[O:30])[CH:22]=[CH:23][C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[CH2:16]1)=[O:14])C1C=CC=CC=1>C(O)C.Cl.C(OCC)(=O)C.O=[Pt]=O>[NH:27]1[CH2:28][CH2:29][CH:24]([CH2:23][CH2:22][C:21]([N:17]2[CH2:18][CH2:19][CH2:20][C@@H:15]([C:13]([NH:12][CH2:11][C@H:10]([NH:31][C:32](=[O:34])[CH3:33])[C:9]([OH:35])=[O:8])=[O:14])[CH2:16]2)=[O:30])[CH2:25][CH2:26]1

Participants

6

Reactant 1

HCID 86588493HCID 86588493, compound

Product 1

HCID 9803820HCID 9803820, compoundYield 79.8%

Reagents, catalysts & solvents 4

HCID 345198Adams' catalystCatalyst2×HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-[(R)-1-[3-(4-pyridyl)-2-propenoyl]-3-piperidylcarbonyl]-2(S)-acetylamino-β-alanine benzyl ester (233 mg), PtO2 (60 mg) in ethanol (10 ml), 4N HCl in ethyl acetate (121 μl) and PtO2 (50% wet, 1.2 g) was stirred vigorously under hydrogen (1 atm) atmosphere. After 3.5 hours, the catalyst was removed by filtration, and the filtrate was evaporated in vacuo. The residue was dissolved in water (10 ml). The solution was adjusted to pH 6.5 with aqueous NaHCO3, then evaporated in vacuo. The residue was purified by ODS-chromatography (Disogel SP-120®) eluting with 4% CH3CN/water. The eluent was concentrated in vacuo and freeze-dried to give N-[(R)-1-[3-(4-piperidyl)propionyl]-3-piperidylcarbonyl]-2(S)-acetylamino-β-alanine (154 mg) as a white powder, which is the compound obtained in Example 8.

Workup

  1. customthe catalyst was removed by filtration
  2. customthe filtrate was evaporated in vacuo
  3. dissolutionThe residue was dissolved in water (10 ml)
  4. customevaporated in vacuo
  5. customThe residue was purified by ODS-chromatography (Disogel SP-120®)
  6. washeluting with 4% CH3CN/water
  7. concentrationThe eluent was concentrated in vacuo
  8. customfreeze-dried

Sources & evidence

ORD record
ord-ebe703dea99f4d2babeb37aa14b89e1d
Source dataset
uspto-grants-2003_03
Patent number
US06538007B1

Reaction notes

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