N,N-Dimethyl-1,3-propanediamine → HCID 70489094, compound

HRID 851365Notes

Reaction equation

HRID 851365 reaction equation
[CH2:1]([C@@H:4]1[N:7]([C:8](=[C:19]([CH3:21])[CH3:20])[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[C:6](=[O:22])[C@H:5]1[N:23]1C(=O)C2=CC=CC=C2C1=O)[CH:2]=[CH2:3].CN(C)CCCN>C(Cl)Cl.CO>[CH2:1]([C@@H:4]1[N:7]([C:8](=[C:19]([CH3:20])[CH3:21])[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[C:6](=[O:22])[CH:5]1[NH2:23])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 70490067HCID 70490067, compound

Product 1

HCID 70489094HCID 70489094, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl 2-[(3S,4S)-4-allyl-3-phthalimido-2-oxo-azetidin-1-yl]-3-methyl-2-butenoate (340 mg) in a mixture of methylene chloride (5 ml) and methanol (2.5 ml) was added N,N-dimethyl-1,3-propanediamine (0.21 ml) and the mixture was stirred at room temperature for 25 hours. After removal of the solvent by evaporation, the residue was dissolved in ethyl acetate and washed with water. Drying over magnesium sulfate and evaporation gave an oil, which was chromatographed on silica gel (3 g) eluting with a mixture of methylene chloride and acetone (6:1) to give benzyl 2-[(4S)-4-allyl-3-amino-2-oxoazetidin-1-yl]-3-methyl-2-butenoate (155 mg) as an oil.

Workup

  1. customAfter removal of the solvent
  2. customby evaporation
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialDrying over magnesium sulfate and evaporation
  6. customgave an oil, which
  7. customwas chromatographed on silica gel (3 g)
  8. washeluting with a mixture of methylene chloride and acetone (6:1)

Sources & evidence

ORD record
ord-2e024b0a354449c299bbdb47a172d734
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

Loading…