Ammonium formate → HCID 18678888, compound

HRID 1634705Notes

Reaction equation

HRID 1634705 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][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=2)(=[O:18])=[O:17])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=1.C([O-])=O.[NH4+]>[Pd].CO.C(OCC)(=O)C>[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:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=2)(=[O:17])=[O:18])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 18678869HCID 18678869, compound

Product 1

HCID 18678888HCID 18678888, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a clear solution of methyl 3-[(4-methoxyphenethyl)-(3-nitrobenzenesulfonyl)-amino]-propionate in 5/1 methanol/ethyl acetate (30 mL) was added 10% Pd/C (300 mg) and ammonium formate (1.79 g, 28.4 mmol). After being stirred at room temperature for 24 h, the catalyst was filtered off through a pad of celite and the filtrate was concentrated. The residue was partitioned between methylene chloride (100 mL) and water (100 mL). Aqueous layer was extracted with another 100 mL of methylene chloride. Combined organic layer was washed with water (100 mL) and brine, dried over Na2SO4, filtered, and concentrated to give methyl 3-[(4-methoxyphenethyl)-(3-aminobenzenesulfonyl)-amino]-propionate (2.8 g, 7.1 mmol) as a yellow gummy product.

Workup

  1. filtrationthe catalyst was filtered off through a pad of celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was partitioned between methylene chloride (100 mL) and water (100 mL)
  4. extractionAqueous layer was extracted with another 100 mL of methylene chloride
  5. washCombined organic layer was washed with water (100 mL) and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5733136add9a4b229bab430432a78637
Source dataset
uspto-grants-2003_01
Patent number
US06506936B1

Reaction notes

Loading…