HCID 140369479, compound → HCID 22849512, compound

HRID 1647113Notes

Reaction equation

HRID 1647113 reaction equation
C(OC([NH:11][C:12]([C:14]1[CH:35]=[CH:34][C:17]([C:18]([N:20]2[CH2:24][CH2:23][CH2:22][C@H:21]2[CH2:25][C:26]([NH:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[O:27])=[O:19])=[CH:16][CH:15]=1)=[NH:13])=O)C1C=CC=CC=1>C(O)(=O)C.[Pd]>[C:12]([C:14]1[CH:35]=[CH:34][C:17]([C:18]([N:20]2[CH2:24][CH2:23][CH2:22][C@H:21]2[CH2:25][C:26]([NH:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[O:27])=[O:19])=[CH:16][CH:15]=1)(=[NH:11])[NH2:13]

Participants

4

Reactant 1

HCID 140369479HCID 140369479, compound

Product 1

HCID 22849512HCID 22849512, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

115 mg of N-[[(S)-1-[p-[N-[(benzyloxy)carbonyl]-amidino]benzoyl]-2-pyrrolidinyl]acetyl]-β-alanine and 50 mg of Pd/C were stirred under hydrogen for 4 hours in 2.5 ml of acetic acid. The catalyst was filtered off and the solution was evaporated. The residue was dissolved in water, evaporated again and chromatographed on silica gel using methanol. 46 mg of N-[[(S)-1-(p-amidino-benzoyl)-2-pyrrolidinyl]acetyl]-βalanine, m.p. >250° C., are obtained.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solution was evaporated
  3. dissolutionThe residue was dissolved in water
  4. customevaporated again
  5. customchromatographed on silica gel

Sources & evidence

ORD record
ord-7f1c229cb4184117b477ab82e6d2d27f
Source dataset
uspto-grants-1995_07
Patent number
US05430024

Reaction notes

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