HCID 140369479, compound → HCID 22849512, compound

HRID 327517Notes

Reaction equation

HRID 327517 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]-β-alanine, 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-026b1ad65ab44340af49c49d83a41e4f
Source dataset
uspto-grants-1993_12
Patent number
US05273982

Reaction notes

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