HCID 58136467, compound → HCID 58136711, compound

HRID 877276Notes

Reaction equation

HRID 877276 reaction equation
[CH:1]1([CH:6]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][N:28]3[C:33](=[O:34])[CH2:32][O:31][C:30]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[N:29]3)=[CH:23][CH:22]=2)[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19])=[CH:12][CH:11]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].C(O)C>[CH:1]1([CH:6]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][N:28]3[C:33](=[O:34])[CH2:32][O:31][C:30]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[N:29]3)=[CH:23][CH:22]=2)[C:7]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:14][CH:15]=2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 58136467HCID 58136467, compound

Product 1

HCID 58136711HCID 58136711, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

50 mg of palladium on carbon (10%) were added to a solution of 46 mg (0.085 mmol) of (2E)-3-{4-[(cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetyl)amino]phenyl}prop-2-enoic acid (Example 96) in 10 ml of ethanol. Under an atmosphere of hydrogen, the mixture was hydrogenated at atmospheric pressure for 2 h. The reaction mixture was then filtered through Tonsil, the filter residue was washed with ethanol and the combined filtrates were concentrated on a rotary evaporator. The crude product was purified by preparative HPLC. This gave 29 mg (63% of theory) of the title compound.

Workup

  1. filtrationThe reaction mixture was then filtered through Tonsil
  2. washthe filter residue was washed with ethanol
  3. concentrationthe combined filtrates were concentrated on a rotary evaporator
  4. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-13ff711b09f846a9b6305238de33f547
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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