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

HRID 1719271Notes

Reaction equation

HRID 1719271 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-be3f676a84784a15b9d25b9b20984f7d
Source dataset
uspto-grants-1985_09
Patent number
US04539152

Reaction notes

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