HCID 178501508, compound → HCID 131723229, compound

HRID 1937815Notes

Reaction equation

HRID 1937815 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[NH:5][C:6](=[O:24])[CH:7]([C:19](=[O:23])[N:20]([CH3:22])[CH3:21])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[NH:18])[NH:16]O)=[CH:11][CH:10]=1>C(O)(=O)C.[Pd]>[C:3]([OH:31])(=[O:2])[CH3:4].[CH3:1][O:2][C:3](=[O:31])[C@@H:4]([NH:5][C:6](=[O:24])[CH:7]([C:19](=[O:23])[N:20]([CH3:22])[CH3:21])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[NH:16])[NH2:18])=[CH:11][CH:10]=1)[CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

4

Reactant 1

HCID 178501508HCID 178501508, compound

Product 1

HCID 131723229HCID 131723229, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

(S)-Cyclohexyl-{2-(R,S)-dimethylcarbamoyl-3-[4-(N-hydroxycarbamimidoyl)-phenyl]-propionylamino}-acetic acid methyl ester (13 g, 30 mmol) was dissolved in acetic acid (150 ml). After addition of palladium on charcoal (10%, 100 mg) the mixture was hydrogenated at 50° C. for 9 hours. The catalyst was filtered off, the solvent evaporated and the residue dissolved in water and lyophilized. Yield: 14.3 g (100%); MS m/z: 417.4 (M+H)+.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated
  3. dissolutionthe residue dissolved in water

Sources & evidence

ORD record
ord-59a67f0fff3948fc8e0db4820a37d0f1
Source dataset
uspto-grants-2002_05
Patent number
US06395737B1

Reaction notes

Loading…