HCID 86752866, compound → HCID 131720741, compound

HRID 965143Notes

Reaction equation

HRID 965143 reaction equation
C([O:8][C:9](=[O:35])[CH:10]([CH:15]1[CH2:32][C:31]2=[CH:33][N:24]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=32)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][NH:17][C:16]1=[O:34])[CH2:11][C:12]([NH2:14])=[O:13])C1C=CC=CC=1>C1COCC1.CCO.[Pd]>[O:34]=[C:16]1[CH:15]([CH:10]([CH2:11][C:12]([NH2:14])=[O:13])[C:9]([OH:35])=[O:8])[CH2:32][C:31]2=[CH:33][N:24]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=32)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][NH:17]1

Participants

4

Reactant 1

HCID 86752866HCID 86752866, compound

Product 1

HCID 131720741HCID 131720741, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of (3RS,10S)-3-(4-biphenyl-4-yl-imidazol-1-yl)-N-(9-oxo-1,8-diaza-tricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraen-10-yl-succinamic acid benzyl ester (190 mg) in THF/EtOH (5/1, 20 mL) was hydrogenated with 10% Pd/C (170 mg) for 8 hours until TLC indicated that the starting compound was consumed. The solution was filtered through a pad of Celite. The filtrate was evaporated and recrystallized (THF/EtOAc) to give 147 mg of (3RS,10S)-3-(4-biphenyl-4-yl-imidazol-1-yl)-N-(9-oxo-1,8-diaza-tricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraen-10-yl-succinamic acid, melting point: 222°-226° C., MS: 604.2 (M+H)+.

Workup

  1. customwas consumed
  2. filtrationThe solution was filtered through a pad of Celite
  3. customThe filtrate was evaporated
  4. customrecrystallized (THF/EtOAc)

Sources & evidence

ORD record
ord-4d726058ae6442b28e9a40f825bd2c4c
Source dataset
uspto-grants-1998_06
Patent number
US05773428

Reaction notes

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