Ammonium Acetate → HCID 69231905, compound

HRID 1181146Notes

Reaction equation

HRID 1181146 reaction equation
[CH3:1][O:2][C:3]([CH2:5][C:6](=O)[CH:7]([O:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)=[O:11])[CH3:8])=[O:4].C([O-])(=O)C.[NH4+:29]>C(O)C>[NH2:29][C:6](=[CH:5][C:3]([O:2][CH3:1])=[O:4])[CH:7]([O:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)=[O:11])[CH3:8]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 58979133HCID 58979133, compound

Product 1

HCID 69231905HCID 69231905, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of biphenyl-4-carboxylic acid 3-methoxycarbonyl-1-methyl-2-oxo-propyl ester (1275 g, 3.9 mol, 1 eq) and ammonium acetate (640 g, 8.3 mol) in ethanol (10 L) was heated with stirring at 70-75° C. until the keto ester compound is completely consumed (1-2 h). The mixture was then kept at 0-5° C. for 1.5 h. The precipitated solid was collected by filtration and washed with hexanes (2.5 L). The product was dried overnight under vacuum at 50° C. to obtain 1244 g (90% yield, 98% HPLC purity) of the title compound.

Workup

  1. temperaturewas heated
  2. customis completely consumed (1-2 h)
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with hexanes (2.5 L)
  5. customThe product was dried overnight under vacuum at 50° C.

Sources & evidence

ORD record
ord-8ccec18b4ae24404b1c24a864d21ba92
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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