Ammonium Acetate → HCID 18348725, compound

HRID 2268020Notes

Reaction equation

HRID 2268020 reaction equation
C([O-])(=O)C.[NH4+].C[O:7][C:8](=O)[C:9]([CH3:23])([CH3:22])[CH2:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=1)=O.C([BH3-])#[N:26].[Na+]>CO>[F:21][C:16]1[CH:15]=[C:14]([CH:12]2[NH:26][C:8](=[O:7])[C:9]([CH3:23])([CH3:22])[CH2:10][CH2:11]2)[CH:19]=[CH:18][C:17]=1[F:20]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride2×HCID 18348738HCID 18348738, compound

Product 1

HCID 18348725HCID 18348725, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ammonium acetate (36.62 g, 475.1 mmol) was dissolved in 200 mL of methanol. To this solution was added methyl-5-(3,4-difluorophenyl)-2,2-dimethyl-5-oxopentanoate (12.76 g, 47.2 mmol) and sodium cyanoborohydride (2.96 g, 47.1 mmol). This reaction mixture was stirred at ambient temperature for 24 hours. Another portion of sodium cyanoborohydride (1.50 g, 23.9 mmol) was added, and the mixture was stirred at ambient temperature for another 66 hours. The reaction mixture was concentrated in vacuo, and the residue was partitioned between dichloromethane and saturated sodium carbonate. A 1.0M solution of aqueous sodium hydroxide was added to the aqueous phase to achieve a pH of 10. The phases were then separated, and the aqueous phase was extracted three more times with dichloromethane. The combined organic phases were then washed once with brine, dried over sodium sulfate, filtered, and the filtrate was evaporated to dryness. This residue was purified by “flash” chromatography (98:2 dichloromethane:methanol). The product fractions were evaporated to dryness to give the title compound as a solid.

Workup

  1. stirringthe mixture was stirred at ambient temperature for another 66 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was partitioned between dichloromethane and saturated sodium carbonate
  4. additionA 1.0M solution of aqueous sodium hydroxide was added to the aqueous phase
  5. customThe phases were then separated
  6. extractionthe aqueous phase was extracted three more times with dichloromethane
  7. washThe combined organic phases were then washed once with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customthe filtrate was evaporated to dryness
  11. customThis residue was purified by “flash” chromatography (98:2 dichloromethane:methanol)
  12. customThe product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-35c42c4c25364bd8a679973a7d99c2a7
Source dataset
uspto-grants-2001_12
Patent number
US06326372B1

Reaction notes

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