HCID 86584075, compound → HCID 86584074, compound

HRID 843742Notes

Reaction equation

HRID 843742 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[CH2:5][C@@H:6]([CH:33]=[CH2:34])[NH:7][C:8]([C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16](=[O:32])[CH2:17][CH2:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[CH2:11]1)=[O:9])[CH3:2]>C(O)C.O=[Pt]=O>[CH2:1]([O:3][C:4](=[O:35])[CH2:5][C@H:6]([CH2:33][CH3:34])[NH:7][C:8]([C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16](=[O:32])[CH2:17][CH2:18][CH:19]2[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])[CH2:23][CH2:24]2)[CH2:11]1)=[O:9])[CH3:2]

Participants

4

Reactant 1

HCID 86584075HCID 86584075, compound

Product 1

HCID 86584074HCID 86584074, compoundYield 90.9%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-[(R)-1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-3(S)-vinyl-β-alanine ethyl ester (0.8 g) and PtO2 (0.2 g) in ethanol (10 ml) was hydrogenated at atmospheric pressure for 2 hours. After the catalyst was removed by filtration, the filtrate was concentrated in vacuo to give N-[(R)-1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-3(S)-ethyl-β-alanine ethyl ester (0.73 g) as a colorless oil.

Workup

  1. customAfter the catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6f6ec2c59643480398f96e67fb1ab0b3
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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