HCID 140369477, compound → HCID 19926231, compound

HRID 1647115Notes

Reaction equation

HRID 1647115 reaction equation
C([O:8][C:9](=[O:40])[CH2:10][CH2:11][NH:12][C:13]([CH:15]1[CH2:20][CH2:19][CH2:18][N:17]([C:21](=[O:39])[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29](=[NH:38])[NH:30]C(OC(C)(C)C)=O)=[CH:25][CH:24]=2)[CH2:16]1)=[O:14])C1C=CC=CC=1>C(O)=O.[Pd]>[C:29]([C:26]1[CH:27]=[CH:28][C:23]([CH2:22][C:21]([N:17]2[CH2:18][CH2:19][CH2:20][CH:15]([C:13]([NH:12][CH2:11][CH2:10][C:9]([OH:40])=[O:8])=[O:14])[CH2:16]2)=[O:39])=[CH:24][CH:25]=1)(=[NH:30])[NH2:38]

Participants

4

Reactant 1

HCID 140369477HCID 140369477, compound

Product 1

HCID 19926231HCID 19926231, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 284Formic AcidSolvent

Procedure

535 mg of rac-N-[[1-[p-[N-(t-butoxycarbonyl)amidino]phenylacetyl]-3-piperdinyl]carbonyl]-β-alanine benzyl ester were allowed to stand in 11 ml of formic acid for 19 hours, and the mixture was treated with 134 mg of Pd/C and stirred under hydrogen for 4 hours. The solution was filtered and evaporated, the residue was dissolved in water and the solution was evaporated again. The product was stirred in acetonitrile, filtered with suction and dried, yielding 272 mg of rac-N-[[1-[(p-amidinophenyl)acetyl]-3-piperidinyl]carbonyl]-β-alanine, MS: 361 (41, M+H).

Workup

  1. filtrationThe solution was filtered
  2. customevaporated
  3. dissolutionthe residue was dissolved in water
  4. customthe solution was evaporated again
  5. stirringThe product was stirred in acetonitrile
  6. filtrationfiltered with suction
  7. customdried

Sources & evidence

ORD record
ord-1bf0db28a73845d88be434f77b3d72fa
Source dataset
uspto-grants-1995_07
Patent number
US05430024

Reaction notes

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