HCID 178512179, compound → HCID 178512902, compound

HRID 2248491Notes

Reaction equation

HRID 2248491 reaction equation
C([O:8][C:9](=[O:46])[CH2:10][CH2:11][NH:12][C:13](=[O:45])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21](=[O:44])[C@H:22]([CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:43])[NH:39][N+]([O-])=O)[NH:23]C(OCC2C=CC=CC=2)=O)[CH:15]=1)C1C=CC=CC=1>C(O)=O.[Pd]>[CH:9]([OH:46])=[O:8].[NH2:23][C@H:22]([C:21]([NH:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[C:13]([NH:12][CH2:11][CH2:10][C:9]([OH:46])=[O:8])=[O:45])=[O:44])[CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:39])[NH2:43]

Participants

4

Reactant 1

HCID 178512179HCID 178512179, compound

Product 1

HCID 178512902HCID 178512902, compoundYield 187%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 284Formic AcidSolvent

Procedure

900 mg of N-[m-[[N2 -[(benzyloxy)carbonyl]-N5 -(N-nitroamidino)-L-ornithyl]amino]benzoyl]-β-alanine benzyl ester and 300 mg of Pd/C (5%) are stirred in 20 ml of formic acid for 18 hours under hydrogen. The reaction mixture is filtered and the filtrate is evaporated in a vacuum. The residue is taken up in water and again evaporated in a vacuum. After drying there are obtained 545 mg of N-[m-(L-arginylamino)benzoyl]-β-alanine formate (2:3), [α]D20 =+39° (H2O, c=0.5%).

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated in a vacuum
  3. customagain evaporated in a vacuum
  4. customAfter drying there

Sources & evidence

ORD record
ord-5659822028784bbb95336bc119a74048
Source dataset
uspto-grants-1991_08
Patent number
US05039805

Reaction notes

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