HCID 178465537, compound → HCID 178476519, compound

HRID 1709359Notes

Reaction equation

HRID 1709359 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:8]([NH:10][C@H:11]([C:16]([NH:18][C@H:19]([C:30]([N:32]1[CH2:39][CH2:38][CH2:37][C@H:33]1[C:34]([OH:36])=[O:35])=[O:31])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:29])[NH:25][N+]([O-])=O)=[O:17])[CH2:12][CH:13]([CH3:15])[CH3:14])=[O:9])[CH2:3][C:4](=[O:7])[O:5][CH3:6].[CH2:50]([NH-:52])[CH3:51]>CO.C(O)(=O)C.[Pd].O>[NH2:1][C@H:2]([C:8]([NH:10][C@H:11]([C:16]([NH:18][C@H:19]([C:30]([N:32]1[CH2:39][CH2:38][CH2:37][C@H:33]1[C:34]([OH:36])=[O:35])=[O:31])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:25])[NH2:29])=[O:17])[CH2:12][CH:13]([CH3:14])[CH3:15])=[O:9])[CH2:3][C:4](=[O:7])[O:5][CH3:6].[C:4]([O-:7])(=[O:5])[CH3:3].[C:4]([O-:7])(=[O:5])[CH3:3].[CH2:50]([NH-:52])[CH3:51]

Participants

6

Reactant 1

HCID 178465537HCID 178465537, compound

Product 1

HCID 178476519HCID 178476519, compoundYield 256%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2.16 g (3.0 millimoles) of Z-Asp(OMe)-Leu-Arg(NO2)-Pro-ethylamide are dissolved in a mixture of 24 ml of methanol and 24 ml of acetic acid, thereafter 900 mg of 10% palladium-on-charcoal catalyst suspended in 24 ml of water are added under stirring and hydrogen gas is bubbled through the reaction mixture for 8 hours. Then the catalyst is filtered off, the filtrate is evaporated and the residue is triturated with ether and dried. Thus 1.73 g (87.3%) of title product are obtained.

Workup

  1. additionare added
  2. customhydrogen gas is bubbled through the reaction mixture for 8 hours
  3. filtrationThen the catalyst is filtered off
  4. customthe filtrate is evaporated
  5. customthe residue is triturated with ether
  6. customdried

Sources & evidence

ORD record
ord-7d390800a3914dadaf5c1acd69bfbd0d
Source dataset
uspto-grants-1990_08
Patent number
US04948873

Reaction notes

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