Ammonium Acetate → HCID 58979133, compound

HRID 1181147Notes

Reaction equation

HRID 1181147 reaction equation
N[C:2](=[CH:20][C:21]([O:23][CH3:24])=[O:22])[CH:3]([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)=[O:7])[CH3:4].C([O-])(=[O:27])C.[NH4+]>C(O)(=O)C>[CH3:24][O:23][C:21]([CH2:20][C:2](=[O:27])[CH:3]([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)=[O:7])[CH3:4])=[O:22]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 69231905HCID 69231905, compound

Product 1

HCID 58979133HCID 58979133, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of biphenyl-4-carboxylic acid 2-amino-3-methoxycarbonyl-1-methyl-allyl ester (566 g, 1.74 mol, 1 eq) and ammonium acetate (283 g, 3.67 mol) in glacial acetic acid (11.3 L) was heated at reflux for 2 h, cooled, and concentrated. The residue was coevaporated with toluene (2×2.5 L) and EtOAc (2.5 L). The mixture was diluted with EtOAc (6.6 L) and transferred with EtOAc (2.2 L) to a bottom outlet separation flask. The mixture was washed twice with water (2.2 L), saturated aqueous NaHCO3 (1.1 L), and brine (2×2.2 L). The organic layer was dried (Na2SO4, 550 g), filtered with the aid of EtOAc (1.1 L), and concentrated. The residue was dissolved in isopropanol (2 L) at 50° C. and allowed to cool overnight at room temperature. The mixture was kept at 0° C. to 5° C. for 1 h. The precipitated solid was broken up and collected by filtration. The solid was washed with cold isopropanol (4×0.55 L) and dried overnight in a vacuum oven at 50° C. to yield 428 g of the title compound (72% from Step 2).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperaturecooled
  4. concentrationconcentrated
  5. additionThe mixture was diluted with EtOAc (6.6 L)
  6. customtransferred with EtOAc (2.2 L) to a bottom outlet
  7. customseparation flask
  8. washThe mixture was washed twice with water (2.2 L), saturated aqueous NaHCO3 (1.1 L), and brine (2×2.2 L)
  9. dry with materialThe organic layer was dried (Na2SO4, 550 g)
  10. filtrationfiltered with the aid of EtOAc (1.1 L)
  11. concentrationconcentrated
  12. dissolutionThe residue was dissolved in isopropanol (2 L) at 50° C.
  13. filtrationcollected by filtration
  14. washThe solid was washed with cold isopropanol (4×0.55 L)
  15. customdried overnight in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-317eafa81e614b148516a0b912fb7d31
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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