HCID 140369483, compound → HCID 10256303, compound

HRID 1647108Notes

Reaction equation

HRID 1647108 reaction equation
C([O:8][C:9](=[O:62])[C@H:10]([CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[NH:11][C:12](=[O:54])[C@H:13]([CH2:43][C:44]([O:46]CC1C=CC=CC=1)=[O:45])[NH:14][C:15](=[O:42])[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:41])[C:22]1[CH:27]=[CH:26][C:25]([C:28](=[NH:40])[NH:29]C(OCC2C=CC=CC=2)=O)=[CH:24][CH:23]=1)C1C=CC=CC=1>C(O)(=O)C.[Pd]>[C:28]([C:25]1[CH:26]=[CH:27][C:22]([C:21]([NH:20][CH2:19][CH2:18][CH2:17][CH2:16][C:15]([NH:14][C@H:13]([C:12]([NH:11][C@H:10]([C:9]([OH:62])=[O:8])[CH2:55][C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=2)=[O:54])[CH2:43][C:44](=[O:45])[OH:46])=[O:42])=[O:41])=[CH:23][CH:24]=1)(=[NH:29])[NH2:40]

Participants

4

Reactant 1

HCID 140369483HCID 140369483, compound

Product 1

HCID 10256303HCID 10256303, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

443 mg of N-[3-[(benzyloxy)carbonyl]-N-[5-[p-[N-[(benzyloxy)carbonyl]amidino]benzamido]valeryl]-L-alanyl]-3-phenyl-L-alanine benzyl ester and 111 mg of Pd/C in 9 ml of acetic acid were stirred under hydrogen gas for 31/2 hours. The solution was filtered and evaporated, the residue was dissolved in water and the solution was again evaporated. The residue was stirred in water, filtered off with suction and dried. 246 mg of N-[N-[5-(p-amidinobenzamido)valeryl]-L-α-aspartyl]-3-phenyl-L-alanine, m.p. 241° C., was obtained as the hydrate (1:2).

Workup

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

Sources & evidence

ORD record
ord-e4db7221d74a4aad990b333ee8958a9a
Source dataset
uspto-grants-1995_07
Patent number
US05430024

Reaction notes

Loading…