Water → HCID 21927816, compound

HRID 1243506Notes

Reaction equation

HRID 1243506 reaction equation
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[NH2:16][C:17](=O)[CH2:18][C:19]([CH3:26])([CH3:25])[CH2:20][C:21]([O:23][CH3:24])=[O:22].C(N(CC)CC)C.O>C(Cl)Cl>[C:17]([CH2:18][C:19]([CH3:26])([CH3:25])[CH2:20][C:21]([O:23][CH3:24])=[O:22])#[N:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 21927859HCID 21927859, compound

Product 1

HCID 21927816HCID 21927816, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (5.4 mL; 31.8 mmoles) was added to an ice cooled solution of methyl 5-amino-3,3-dimethyl-5-oxopentanoate (5.00 g; 28.9 mmoles) in methylene chloride (250 mL) and triethylamine (8 mL; 57.8 mmoles), under nitrogen while keeping the temperature below 5° C. The reaction mixture was allowed to warm to room temperature and stirred for 30 minutes. Water (125 mL) was added and the phases were separated. The aqueous phase was extracted with methylene chloride (100 mL). The organic phases were combined, washed with saturated aqueous sodium chloride solution and dried over sodium sulfate. The solution was filtered and the solvent was removed under vacuum to give the product, methyl 4-cyano-3,3-dimethylbutanoate (3.1 g; 69%). 1H NMR (400 MHz) DMSO-d6 δ 3.60 (3H, s), 2.61 (2H, s), 2.35 (2H, s), 1.07 (6H, s).

Workup

  1. customthe temperature below 5° C
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with methylene chloride (100 mL)
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationThe solution was filtered
  7. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-28d0db5835e84f14801e91359bebea73
Source dataset
uspto-grants-2006_10
Patent number
US07119098B2

Reaction notes

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