Ethanol → HCID 53963459, compound

HRID 1357855Notes

Reaction equation

HRID 1357855 reaction equation
O.O.C1(C)C=CC=CC=1NC1NC2C=C(CC([NH:22][C:23]3[CH:28]=[CH:27][C:26]([C@H:29]([CH3:34])[CH2:30][C:31]([OH:33])=[O:32])=[CH:25][CH:24]=3)=O)C=CC=2N=1.C([O-])=O.[NH4+].[CH2:40](O)[CH3:41]>[Pd]>[NH2:22][C:23]1[CH:24]=[CH:25][C:26]([C@H:29]([CH3:34])[CH2:30][C:31]([O:33][CH2:40][CH3:41])=[O:32])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 2723923Ammonium formateHCID 69532798(R)-3-{4-[2-(2-o-tolylamino-3H-benzimidazol-5-yl)acetylamino]phenyl}butanoic acid dihydrate

Product 1

HCID 53963459HCID 53963459, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
50 °C

Procedure

A solution of ethyl 3(R)-(4-nitrophenyl)butanoate (4.0 g, Reference Example 2) in ethanol (100 mL) was treated with ammonium formate (about 15 g). The reaction mixture was immersed in an oil-bath in a single neck flask, the solution was heated to 50° C., then treated with palladium on charcoal (about 1 g, 5%) to give an immediate visible effervescence. The mixture was kept at 50° C. with stirring for about an hour, then filtered through filter-aid. The filtrate was evaporated and the residue was partitioned between tert-butyl methyl ether and water. The organic phase was dried then evaporated to give the title compound (2.8 g) as a light brown gum.

Workup

  1. customThe reaction mixture was immersed in an oil-bath in a single neck flask
  2. customto give an immediate visible effervescence
  3. customwas kept at 50° C.
  4. filtrationfiltered
  5. filtrationthrough filter-aid
  6. customThe filtrate was evaporated
  7. customthe residue was partitioned between tert-butyl methyl ether and water
  8. customThe organic phase was dried
  9. customthen evaporated

Sources & evidence

ORD record
ord-831c250e48fb49198351168150d6ae95
Source dataset
uspto-grants-2003_07
Patent number
US06593354B2

Reaction notes

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