Ammonium formate → HCID 25164597, compound

HRID 1098741Notes

Reaction equation

HRID 1098741 reaction equation
C([O:3][C:4](=[O:19])[CH2:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[NH:18])[NH:16]O)=[CH:11][CH:10]=1)=[O:7])C.C([O-])=O.[NH4+]>C(O)(=O)C>[C:15]([C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:6](=[O:7])[CH2:5][C:4]([OH:19])=[O:3])=[CH:14][CH:13]=1)(=[NH:16])[NH2:18]

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 178472237HCID 178472237, compound

Product 1

HCID 25164597HCID 25164597, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of N-[4-(N-hydroxycarbamimidoyl)-phenyl]-malonamic acid ethyl ester (16.9 g, 63.41 mmol) and ammonium formiate (20.0 g, 317.1 mmol) in glacial acetic acid (400 ml) Pd/C, 10% (675 mg) was added. The suspension was stirred for 5 h under reflux. The reaction mixture was filtered through celite and evaporated. The crude product was dissolved in ethanol (400 ml) and treated with an aqueous solution of sodium hydroxide (2 M, 300 ml). The reaction mixture was stirred for 4 h at RT and then hydrochloric acid (2 N) was added (pH=8). The suspension was filtered and the solid was dissolved in ACN/water and acidified with trifluoroacetic acid (pH=1). Lyophilization left the product (9.88 g, 46%) as a white solid.

Workup

  1. temperatureunder reflux
  2. filtrationThe reaction mixture was filtered through celite
  3. customevaporated
  4. dissolutionThe crude product was dissolved in ethanol (400 ml)
  5. additiontreated with an aqueous solution of sodium hydroxide (2 M, 300 ml)
  6. stirringThe reaction mixture was stirred for 4 h at RT
  7. additionhydrochloric acid (2 N) was added (pH=8)
  8. filtrationThe suspension was filtered
  9. dissolutionthe solid was dissolved in ACN/water
  10. waitLyophilization left the product (9.88 g, 46%) as a white solid

Sources & evidence

ORD record
ord-81af5f3f43854c0dbb1487005e360bc7
Source dataset
uspto-grants-2012_03
Patent number
US08143242B2

Reaction notes

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