5-[1-(3-Phenyl-allyl)-1H-imidazol-4-yl]-4-(7-phenyl-heptanoylamino)-pent-2-enoic acid ethyl ester → 4-(7-Phenyl-heptanoylamino)-5-[1-(3-phenyl-propyl)-1H-imidazol-4-yl]-pentanoic acid ethyl ester

HRID 852864Notes

Reaction equation

HRID 852864 reaction equation
[CH2:1]([O:3][C:4](=[O:38])[CH:5]=[CH:6][CH:7]([NH:23][C:24](=[O:37])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:8][C:9]1[N:10]=[CH:11][N:12]([CH2:14][CH:15]=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:38])[CH2:5][CH2:6][CH:7]([NH:23][C:24](=[O:37])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:8][C:9]1[N:10]=[CH:11][N:12]([CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=1)[CH3:2]

Participants

4

Reactant 1

HCID 694153655-[1-(3-Phenyl-allyl)-1H-imidazol-4-yl]-4-(7-phenyl-heptanoylamino)-pent-2-enoic acid ethyl ester

Product 1

HCID 694170144-(7-Phenyl-heptanoylamino)-5-[1-(3-phenyl-propyl)-1H-imidazol-4-yl]-pentanoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-[1-(3-phenyl-allyl)-1H-imidazol-4-yl]-4-(7-phenyl-heptanoylamino)-pent-2-enoic acid ethyl ester (110 mg, 0.21 mmol) and Pd/C (50 mg) in ethanol (100 mL) was subject to hydrogenation (42 psi) for 2 hr. The solution was filtered and the solvent removed. The residue, ESMS 518 (M+H+) was hydrolysed directly without characterisation.

Workup

  1. filtrationThe solution was filtered
  2. customthe solvent removed

Sources & evidence

ORD record
ord-2d77506d1fe04f6d8761d15310726512
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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