Sodium Methoxide → HCID 136146841, compound

HRID 1674412Notes

Reaction equation

HRID 1674412 reaction equation
[F:1][CH:2]([CH3:11])[C:3](=O)[CH2:4][C:5]([O:7]CC)=O.Cl.[C:13](=[NH:18])([NH2:17])[CH2:14][CH2:15][CH3:16].C[O-].[Na+]>CO.C(OCC)(=O)C>[F:1][CH:2]([C:3]1[N:17]=[C:13]([CH2:14][CH2:15][CH3:16])[NH:18][C:5](=[O:7])[CH:4]=1)[CH3:11]

Participants

6

Reactant 3

HCID 10942334Sodium MethoxideHCID 11263671ETHYL 4-FLUORO-3-OXOPENTANOATEHCID 12828983Butanimidamide hydrochloride

Product 1

HCID 136146841HCID 136146841, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 4-fluoro-3-oxopentanoate (5.0 g), butanimidamide hydrochloride (4.6 g) and sodium methoxide (28% methanol solution, 16 mL) in methanol (50 mL) was stirred overnight. The reaction mixture was diluted with ethyl acetate, washed with 1 M hydrochloric acid, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale yellow oil (5.7 g, 100%).

Workup

  1. washwashed with 1 M hydrochloric acid
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b567ab3c57814d23a6ec5b639e84a780
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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