Methanol → 3-Amino-1-(2-methoxycarbonyl-1-phenylethyl)-2-azetidinone

HRID 1706526Notes

Reaction equation

HRID 1706526 reaction equation
C1(=O)[N:5]([CH:6]2[CH2:9][N:8]([CH:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:7]2=[O:22])C(=O)C2=CC=CC=C12.CN(C)CCCN.CO.C(Cl)(Cl)Cl>C(OCC)(=O)C>[NH2:5][CH:6]1[CH2:9][N:8]([CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:7]1=[O:22]

Participants

6

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 23463638HCID 23463638, compound

Product 1

HCID 539654873-Amino-1-(2-methoxycarbonyl-1-phenylethyl)-2-azetidinoneYield 82.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Phthalimido-1-(2-methoxycarbonyl-1-phenylethyl)-2-azetidinone (1.90 g.) and N,N-dimethyl-1,3-propanediamine (1.14 g.) were added to a mixture of methanol (20 ml.) and chloroform (5 ml.), whereafter the mixture was stirred at ambient temperature for 17 hours. The reaction mixture was evaporated to dryness under reduced pressure to give a residue, which was dissolved in ethyl acetate (20 ml.). The solution was extracted with three portions of an aqueous solution consisting of 1 N hydrochloric acid (5.3 ml.) and water (11.3 ml.), and then the combined extract was washed with ethyl acetate. The aqueous solution was adjusted to pH 8 with sodium bicarbonate under ice-cooling and then extracted with three 10 ml. portions of chloroform. The extracts were washed with water and then dried over magnesium sulfate. The solvent was removed by distillation from the solution under reduced pressure to give oily 3-amino-1-(2-methoxycarbonyl-1-phenylethyl)-2-azetidinone (1.030 g.).

Workup

  1. customThe reaction mixture was evaporated to dryness under reduced pressure
  2. customto give a residue, which
  3. extractionThe solution was extracted with three portions of an aqueous solution
  4. extractionthe combined extract
  5. washwas washed with ethyl acetate
  6. temperaturecooling
  7. extractionextracted with three 10 ml
  8. washThe extracts were washed with water
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was removed by distillation from the solution under reduced pressure

Sources & evidence

ORD record
ord-67c3f9330db54dec966e098c979dc729
Source dataset
uspto-grants-1980_06
Patent number
US04207234

Reaction notes

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