Water → HCID 66973058, compound

HRID 1367194Notes

Reaction equation

HRID 1367194 reaction equation
Cl.[NH2:2][C:3]1([C:8]([O:10][CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1.Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15].C([O-])(O)=O.[Na+].O>CN(C=O)C>[O:15]=[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:13][NH:2][C:3]1([C:8]([O:10][CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 6259Phenacyl bromideHCID 516892Sodium BicarbonateHCID 11513856Methyl 1-amino-1-cyclopentanecarboxylate, HCl2×

Product 1

HCID 66973058HCID 66973058, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 1-aminocyclopentanecarboxylate hydrochloride (2.00 g, 11.1 mmol, described in Intermediate 25), 2-bromoacetophenone (2.44 g, 12.2 mmol), and NaHCO3 (2.34 g, 27.9 mmol) in DMF (20 mL) was stirred at ambient temperature for 5 h. H2O (25 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=262 (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-dacd424f12cd4cb8973dd4236beb74aa
Source dataset
uspto-grants-2011_02
Patent number
US07893079B2

Reaction notes

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