Acetic Acid → HCID 178512520, compound

HRID 1415675Notes

Reaction equation

HRID 1415675 reaction equation
C([NH:11][C:12](=[NH:41])[NH:13][C:14]1[CH:40]=[CH:39][C:17]([C:18]([N:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][C:29]([O:31]CC3C=CC=CC=3)=[O:30])[CH2:22][CH2:21]2)=[O:19])=[CH:16][CH:15]=1)(OCC1C=CC=CC=1)=O.O.C(O)(=O)C>CO.[Pd]>[NH:13]([C:14]1[CH:15]=[CH:16][C:17]([C:18]([N:20]2[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH2:24][CH2:25]2)=[O:19])=[CH:39][CH:40]=1)[C:12]([NH2:41])=[NH:11]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 178512413HCID 178512413, compound

Product 1

HCID 178512520HCID 178512520, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1 g of benzyl 4-(4-(4-(3-CBZ-guanidino)benzoyl)piperazin-1-yl)butyrate (FAB 558; obtainable by condensing 4-(3-CBZ-guanidino)benzoic acid with benzyl 4-(piperazin-1-yl)butyrate) in a mixture of 38 ml of methanol, 6 ml of water and 6 ml of acetic acid is hydrogenated on 0.6 g of 5% Pd/C at 20° and 1 bar until the uptake of H2 has ceased. It is filtered, the filtrate is evaporated and the residue is recrystallized from ethyl acetate to give 4-(4-(4-guanidinobenzoyl)piperazin-1-yl)butyric acid, FAB 334.

Workup

  1. filtrationIt is filtered
  2. customthe filtrate is evaporated
  3. customthe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fdfed0ba8f37443da256195c68fd5c6f
Source dataset
uspto-grants-1999_06
Patent number
US05908843

Reaction notes

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