HCID 67719824, compound → HCID 67719716, compound

HRID 1941095Notes

Reaction equation

HRID 1941095 reaction equation
C(OC([NH:8][N:9]=[CH:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:42])[NH:19][CH2:20][C:21]([NH:23][CH:24]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:25][C:26]([O:28]CC2C=CC=CC=2)=[O:27])=[O:22])=[CH:13][CH:12]=1)=O)(C)(C)C.[H][H]>CN(C=O)C.[Pd]>[NH2:8][N:9]=[CH:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:42])[NH:19][CH2:20][C:21]([NH:23][CH:24]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:25][C:26]([OH:28])=[O:27])=[O:22])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 67719824HCID 67719824, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67719716HCID 67719716, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

0.38 g (0.66 mmol) of benzyl 3-((3-(4-(tert-butyloxycarbonylaminoiminomethyl)phenyl)ureido)acetylamino)-3-phenylpropionate is dissolved in 30 ml of DMF and treated with 0.07 g of Pd/C (10%). Hydrogen is then passed through for 24 h, solid is filtered off, the filtrate is concentrated in vacuo and the residue is treated with 1.53ml of trifluoroacetic acid (99%) and 0.15 ml of water. After stirring at room temperature for 48 h, the mixture is concentrated in vacuo and the residue is chromatographed on Sephadex (LH-20).

Workup

  1. customis then passed through for 24 h, solid
  2. filtrationis filtered off
  3. concentrationthe filtrate is concentrated in vacuo
  4. additionthe residue is treated with 1.53ml of trifluoroacetic acid (99%) and 0.15 ml of water
  5. concentrationthe mixture is concentrated in vacuo
  6. customthe residue is chromatographed on Sephadex (LH-20)

Sources & evidence

ORD record
ord-bc9ee5a5e33b48768db2b62c5eb02872
Source dataset
uspto-grants-1997_12
Patent number
US05703050

Reaction notes

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