Ethanol → HCID 54354360, compound

HRID 1018009Notes

Reaction equation

HRID 1018009 reaction equation
[CH3:1][O:2][C:3](=[O:46])[CH2:4][C@@H:5]([NH:35]C(OCC1C=CC=CC=1)=O)[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:34])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH3:31])=[O:23])=[C:17]([O:32][CH3:33])[CH:16]=2)=[CH:8][CH:7]=1.C(O)C>[Pd].C(O)=O>[CH3:1][O:2][C:3](=[O:46])[CH2:4][C@@H:5]([NH2:35])[C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:34])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH3:31])=[O:23])=[C:17]([O:32][CH3:33])[CH:16]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 54155485HCID 54155485, compound

Product 1

HCID 54354360HCID 54354360, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 284Formic AcidSolvent

Procedure

A mixture of (R)-3-benzyloxycarbonylamino-3-(4-{3-methoxy-4-[3-(2-methylphenyl)ureido]-phenylacetylamino}phenyl)-propanoic acid methyl ester (18.55 g), ethanol (750 ml) and formic acid (18 ml), under an atmosphere of hydrogen, was heated at reflux. The reaction was treated portionwise with 10% palladium on charcoal (3.0 g) over a period of 1 hour and then heated at reflux for a further 1 hour. The reaction mixture was filtered through a short pad of diatomaceous earth and the filter pad was washed three times with ethanol (75 ml) and water (75 ml). The combined filtrate and washings were evaporated. The residue was treated carefully with aqueous solution of sodium bicarbonate (600 ml, 0.6M) followed by stirring for 15 minutes. The resultant white solid was collected, washed twice with water (100 ml), then boiled in acetonitrile in the presence of activated charcoal (150 mg). The mixture was filtered through a short pad of diatomaceous earth while hot and the filtrate cooled in ice to yield the title compound (7.6 g) as a white solid m.p. 189-191° C.

Workup

  1. temperatureunder an atmosphere of hydrogen, was heated
  2. temperatureat reflux
  3. temperatureheated
  4. temperatureat reflux for a further 1 hour
  5. filtrationThe reaction mixture was filtered through a short pad of diatomaceous earth
  6. washthe filter pad was washed three times with ethanol (75 ml) and water (75 ml)
  7. customThe combined filtrate and washings were evaporated
  8. additionThe residue was treated carefully with aqueous solution of sodium bicarbonate (600 ml, 0.6M)
  9. customThe resultant white solid was collected
  10. washwashed twice with water (100 ml)
  11. filtrationThe mixture was filtered through a short pad of diatomaceous earth while hot and the filtrate
  12. temperaturecooled in ice

Sources & evidence

ORD record
ord-919241d233f94eeb8e8666d6f34739bc
Source dataset
uspto-grants-2002_11
Patent number
US06479519B1

Reaction notes

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