Ammonium formate → HCID 25135868, compound

HRID 2250187Notes

Reaction equation

HRID 2250187 reaction equation
C([O-])=O.[NH4+].[CH3:5][O:6][C:7](=[O:33])[C@H:8]([NH:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[C:12]([N+:19]([O-])=O)[CH:11]=1>[Zn].CO>[CH3:5][O:6][C:7](=[O:33])[C@H:8]([NH:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([NH2:19])[CH:11]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 25135866HCID 25135866, compound

Product 1

HCID 25135868HCID 25135868, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Solid ammonium formate (2.27 g, 36 mmol) was added in small portions at 0° C. to a methanol (50 mL, degassed with nitrogen for 2 h) suspension of (R)-2-benzyloxycarbonylamino-3-(3,4-dinitro-phenyl)-propionic acid methyl ester (1.45 g, 3.6 mmol) and zinc powder (1.41 g, 21.6 mmol). The resulting mixture was stirred at room temperature overnight. The solvents were removed in vacuo and then toluene (30 mL, degassed) and ethyl acetate (30 mL, degassed) were added, followed by acetic acid (3 mL). The mixture was further diluted until all organic solids dissolved, then it was washed with water, brine and dried over sodium sulfate. After filtration, solvents were removed in vacuo to afford the title compound containing 1 equivalent of acetic acid as a reddish gummy solid (85%). Mass Spec.: 344.18 (MH)+.

Workup

  1. customThe solvents were removed in vacuo
  2. additiontoluene (30 mL, degassed) and ethyl acetate (30 mL, degassed) were added
  3. additionThe mixture was further diluted until all organic solids
  4. dissolutiondissolved
  5. washit was washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter filtration, solvents
  8. customwere removed in vacuo

Sources & evidence

ORD record
ord-86991b5a941349d5b39878e0fcb869c5
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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