Methyl 4,4-dimethyl-2-oxocyclopentane-1-carboxylate → HCID 178423155, compound

HRID 1010841Notes

Reaction equation

HRID 1010841 reaction equation
CO[C:3]([CH:5]1[CH2:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]1=O)=[O:4].[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([F:23])=[C:18]([CH:22]=1)[C:19]([NH2:21])=[NH:20]>C(O)C>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([F:23])=[C:18]([C:19]2[N:20]=[C:3]([OH:4])[C:5]3[CH2:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=3[N:21]=2)[CH:22]=1

Participants

4

Reactant 2

HCID 11789638Methyl 4,4-dimethyl-2-oxocyclopentane-1-carboxylateHCID 219309795-Chloro-2-fluorobenzene-1-carboximidamide

Product 1

HCID 178423155HCID 178423155, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4,4-Dimethyl-2-oxo-cyclopentanecarboxylic acid methyl ester (2.08 g, 12.21 mmol) and 5-Chloro-2-fluoro-benzamidine (2.32 g, 13.44 mmol) in 100% ethanol (40 mL) was heated to reflux overnight, then cooled and evaporated. The residue was dissolved in 1N (aq.) NaOH (50 mL) and washed with methylene chloride (2×50 mL). The aqueous layer was then acidified with glacial acetic acid to pH 4 and extracted with methylene chloride (2×100 mL). The organic extracts were dried (brine and MgSO4) and evaporated to give crude product, which was purified by chromatography (CH2Cl2, 0-10% MeOH) to give the desired product as a cream solid (2.10 g, 59% yield).

Workup

  1. temperatureto reflux overnight
  2. temperaturecooled
  3. customevaporated
  4. dissolutionThe residue was dissolved in 1N (aq.) NaOH (50 mL)
  5. washwashed with methylene chloride (2×50 mL)
  6. extractionextracted with methylene chloride (2×100 mL)
  7. dry with materialThe organic extracts were dried (brine and MgSO4)
  8. customevaporated
  9. customto give crude product, which
  10. customwas purified by chromatography (CH2Cl2, 0-10% MeOH)

Sources & evidence

ORD record
ord-133b06454a1644b49b18b2f1217db038
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

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