HCID 178491600, compound → HCID 178491599, compound

HRID 2248493Notes

Reaction equation

HRID 2248493 reaction equation
C([O:8][C:9](=[O:48])[CH2:10][CH2:11][NH:12][C:13](=[O:47])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([NH:22][C:23](=[O:46])[C@H:24]([CH2:36][CH2:37][CH2:38][NH:39][C:40](=[NH:45])[NH:41][N+]([O-])=O)[NH:25]C(OCC2C=CC=CC=2)=O)[CH:15]=1)C1C=CC=CC=1>C(O)=O.[Pd]>[CH:9]([OH:48])=[O:8].[NH2:25][C@H:24]([C:23]([NH:22][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=1[O:20][CH3:21])[C:13]([NH:12][CH2:11][CH2:10][C:9]([OH:48])=[O:8])=[O:47])=[O:46])[CH2:36][CH2:37][CH2:38][NH:39][C:40](=[NH:41])[NH2:45]

Participants

4

Reactant 1

HCID 178491600HCID 178491600, compound

Product 1

HCID 178491599HCID 178491599, compoundYield 150.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 284Formic AcidSolvent

Procedure

390 mg of N-[3-[[N2 -(benzyloxycarbonyl)-N5 -(N-nitroamidino)-L-ornithyl]amino]-p-anisoyl]-β-alanine benzyl ester and 160 mg of Pd/C (5%) are stirred in 8 ml of formic acid for 5 hours under hydrogen. The filtered solution is evaporated and the residue is purified on silica gel with methanol-formic acid (99:1). There are obtained 195 mg of N-[3-(L-arginylamino)-p-anisoyl]-β-alanine formate (1:2), [α]D20 =+46.6° (H2O, c=0.5%).

Workup

  1. customThe filtered solution is evaporated
  2. customthe residue is purified on silica gel with methanol-formic acid (99:1)

Sources & evidence

ORD record
ord-04f605d4f11744a4b94719f3130b8271
Source dataset
uspto-grants-1991_08
Patent number
US05039805

Reaction notes

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