HCID 140369488, compound → HCID 19926324, compound

HRID 1647105Notes

Reaction equation

HRID 1647105 reaction equation
C([O:8][C:9](=[O:40])[CH2:10][CH2:11][NH:12][C:13](=[O:39])[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:38])[C:19]1[CH:24]=[CH:23][C:22]([C:25](=[NH:37])[NH:26]C(OCC2C=CC=CC=2)=O)=[CH:21][CH:20]=1)C1C=CC=CC=1>C(O)(=O)C.[Pd]>[C:25]([C:22]1[CH:21]=[CH:20][C:19]([C:18]([NH:17][CH2:16][CH2:15][CH2:14][C:13]([NH:12][CH2:11][CH2:10][C:9]([OH:40])=[O:8])=[O:39])=[O:38])=[CH:24][CH:23]=1)(=[NH:26])[NH2:37]

Participants

4

Reactant 1

HCID 140369488HCID 140369488, compound

Product 1

HCID 19926324HCID 19926324, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

512 mg of N-[4-[p-[N-(benzyloxycarbonyl)amidino]benzamido]butyryl]-β-alanine benzyl ester and 170 mg of Pd/C in 10 ml of acetic acid were stirred under hydrogen. The catalyst was filtered off and the filtrate was evaporated. The residue was dissolved in water and the solution was evaporated. The residue was suspended in water, adjusted to pH 7 using ammonia, filtered with suction, washed with water and dried. 239 mg of N-[4-(p-amidinobenzamido)butyryl]-β-alanine, m.p. >250° C., MS: 321 (12, M+H), were obtained.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in water
  4. customthe solution was evaporated
  5. filtrationfiltered with suction
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-10f97fd2328249dd958e735c131386a9
Source dataset
uspto-grants-1995_07
Patent number
US05430024

Reaction notes

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