HCID 86587229, compound → HCID 86587228, compound

HRID 2414695Notes

Reaction equation

HRID 2414695 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][C:9]([N:11]2[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]([NH:19][CH2:20][C@H:21]([NH:25][C:26](=[O:41])[C:27]3[CH:32]=[CH:31][C:30]([O:33]CC4C=CC=CC=4)=[CH:29][CH:28]=3)[C:22]([OH:24])=[O:23])=[O:18])[CH2:12]2)=[O:10])[CH2:3][CH2:2]1.[H][H]>CO.[Pd]>[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][C:9]([N:11]2[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]([NH:19][CH2:20][C@H:21]([NH:25][C:26](=[O:41])[C:27]3[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=3)[C:22]([OH:24])=[O:23])=[O:18])[CH2:12]2)=[O:10])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 86587229HCID 86587229, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86587228HCID 86587228, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-[(R)-1-{3-(4-piperidyl)propionyl}-3-piperidylcarbonyl]-2(S)-(4-benzyloxybenzoyl)amino-β-alanine (190 mg, 0.34 mmol) and 10% Pd—C (50% wet) (60 mg) in methanol (7 mL) was hydrogenated at 1 atm of hydrogen. After 5 hours, the catalyst was removed by filtration, then the filtrate was evaporated in vacuo. The residue was purified by an ODS column chromatography using Daisogel-120SP (10% CH3CN/water)and freeze-dried to give N-[(R)-1-{3-(4-piperidyl)propionyl}-3-piperidylcarbonyl]-2(S)-(4-hydroxybenzoyl)amino-β-alanine (153 mg, 0.32 mmol, 94.1%) as a white powder

Workup

  1. customthe catalyst was removed by filtration
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by an ODS column chromatography
  4. customfreeze-dried

Sources & evidence

ORD record
ord-d5c390b015f5439b9813e44d6a35c834
Source dataset
uspto-grants-2004_11
Patent number
US06812235B2

Reaction notes

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