Ammonium formate → HCID 18678924, compound

HRID 1634712Notes

Reaction equation

HRID 1634712 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][CH2:8][N:9]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=1.CO.C(OCC)(=O)C.C([O-])=O.[NH4+]>C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH2:8][N:9]([S:16]([C:19]2[CH:20]=[CH:21][C:22]([NH2:25])=[CH:23][CH:24]=2)(=[O:17])=[O:18])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 2723923Ammonium formateHCID 18678889HCID 18678889, compoundHCID 21584119Ethylacetate methanol

Product 1

HCID 18678924HCID 18678924, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 297MethaneSolvent

Procedure

To a clear solution of methyl 3-[(4-methoxyphenethyl)-(4-nitrobenzensulfonyl)-amino]-propionate in 5:1 methanol/ethyl acetate (4.2 mL/mmol) is added by portion palladium (10%) in charcoal solid (10% w/w), followed by ammonium formate (4 eq.). The resulting mixture is refluxed for 6 hours and filtered through a pad of celite. Filtrate is concentrated and partitioned between ethyl acetate and water. The organic layer is washed with brine, dried over sodium sulfate, filtered and concentrated to give methyl 3-[(4-methoxyphenethyl)-(4-aminobenzenesulfonyl)-amino]-propionate as a brown oily product in quantitative yield.

Workup

  1. temperatureThe resulting mixture is refluxed for 6 hours
  2. filtrationfiltered through a pad of celite
  3. concentrationFiltrate is concentrated
  4. custompartitioned between ethyl acetate and water
  5. washThe organic layer is washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ed3fe9f05db040ee8c3d33cb10a1778d
Source dataset
uspto-grants-2003_01
Patent number
US06506936B1

Reaction notes

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