HCID 140369477, compound → HCID 19926231, compound

HRID 327519Notes

Reaction equation

HRID 327519 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-2c88129c34394e0ba796b1f21de13a33
Source dataset
uspto-grants-1993_12
Patent number
US05273982

Reaction notes

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