Ethanol → HCID 67827891, compound

HRID 2248502Notes

Reaction equation

HRID 2248502 reaction equation
C([O:8][C:9](=[O:47])[CH2:10][CH2:11][NH:12][C:13](=[O:46])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21](=[O:45])[C@H:22]([CH2:31][CH2:32][CH2:33][NH:34]C(OCC2C=CC=CC=2)=O)[NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:15]=1)C1C=CC=CC=1.C(O)C>[Pd].C(O)(=O)C>[C:9]([OH:47])(=[O:8])[CH3:10].[C:27]([O:26][C:24]([NH: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:47])=[O:8])=[O:46])=[O:45])[CH2:31][CH2:32][CH2:33][NH2:34])=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

5

Reactant 2

HCID 702EthanolHCID 53702692HCID 53702692, compound

Product 1

HCID 67827891HCID 67827891, compoundYield 178.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

500 mg of N-[m-[[N5 -(benzyloxycarbonyl)-N2 -t-butoxycarbonyl-L-ornithyl]amino]benzoyl]-β-alanine benzyl ester, 10 ml of ethanol, 0.05 ml of acetic acid and 125 mg of Pd/C are stirred under hydrogen for 3.5 hours. The reaction mixture is filtered and the filtrate is evaporated in a vacuum. There are obtained 333 mg of N-[m-[[(S)-N2 -(t-butoxycarbonyl)-L-ornithyl]amino]benzoyl]-β-alanine acetate (1:1), [α]D =-18.1° (MeOH, c=0.44%).

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated in a vacuum

Sources & evidence

ORD record
ord-7818e2ecf27e4f8d85dbecb405829fe8
Source dataset
uspto-grants-1991_08
Patent number
US05039805

Reaction notes

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