Water → HCID 66973047, compound

HRID 1864901Notes

Reaction equation

HRID 1864901 reaction equation
Cl.[NH2:2][C:3]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4]1.Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14].C([O-])(O)=O.[Na+].O>CN(C=O)C>[O:14]=[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:12][NH:2][C:3]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 6259Phenacyl bromideHCID 386203Ethyl 1-aminocyclopropane-1-carboxylate hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 66973047HCID 66973047, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 1-aminocyclopropanecarboxylate hydrochloride (1.0 g, 7.74 mmol), 2-bromoacetophenone (3.08 g, 15.5 mmol), and NaHCO3 (1.30 g, 15.5 mmol) in DMF (20 mL) was stirred at ambient temperature for 18 h. H2O (20 mL) was added and the mixture was extracted with EtOAc (2×75 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H-90:10:0.1 to 5:95:0.1. The product-containing fractions were combined, adjusted to pH 10 by addition of saturated aqueous Na2CO3 and extracted with EtOAc (2×75 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to provide the title compound. MS: m/z=248 (M+1).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×75 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by HPLC
  6. washeluting with a gradient of H2O
  7. additionadjusted to pH 10 by addition of saturated aqueous Na2CO3
  8. extractionextracted with EtOAc (2×75 mL)
  9. dry with materialThe combined organic layers were dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-29bc299fb39b4f8ca4755e7498920257
Source dataset
uspto-grants-2009_12
Patent number
US07625901B2

Reaction notes

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