Ammonium Acetate → HCID 15434755, compound

HRID 1600884Notes

Reaction equation

HRID 1600884 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][CH:6]([N+:17]([O-])=O)[CH2:7][C:8]1[C:16]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1.C([O-])(=O)C.[NH4+]>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.[Ni]>[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][CH:6]([NH2:17])[CH2:7][C:8]1[C:16]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1

Participants

5

Reactant 2

HCID 517165Ammonium AcetateHCID 15434754HCID 15434754, compound

Product 1

HCID 15434755HCID 15434755, compoundYield 57.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterSolvent

Procedure

To a solution of 165 mg (0.595 mM) of 4-Nitro-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)-pentanoic acid methyl ester in 15 mL of acetic add was added 450 mg (0.595 mM) of ammonium acetate and approximately 100 mg of Raney nickel. The mixture was hydrogenated at 50 psi for 12 hours. The mixture was filtered and the solvent evaporated. The residue was treated with an equal volume of ethyl acetate and saturated sodium bicarbonate. The ethyl acetate layer was dried and evaporated to yield 85 mg of product which was used in the next synthetic step without further purification. TLC: (10:1 CHCl3 : CH3OH) Rf=0.1 Mass Spectrum: m/e=248 (P+1).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent evaporated
  3. additionThe residue was treated with an equal volume of ethyl acetate and saturated sodium bicarbonate
  4. dry with materialThe ethyl acetate layer was dried
  5. customevaporated

Sources & evidence

ORD record
ord-136e4acbd27147ad833e1fe8fac286dd
Source dataset
uspto-grants-1999_11
Patent number
US05977131

Reaction notes

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