N,N-Dimethyl-1,3-propanediamine → methyl [(3R,4R)-3-amino-4-allyl-2-oxoazetidin-1-yl]-3-methylbut-2-enoate

HRID 851367Notes

Reaction equation

HRID 851367 reaction equation
[CH2:1]([C@H:4]1[N:7]([C:8](=[C:13]([CH3:15])[CH3:14])[C:9]([O:11][CH3:12])=[O:10])[C:6](=[O:16])[C@@H:5]1[N:17]1C(=O)C2=CC=CC=C2C1=O)[CH:2]=[CH2:3].CN(C)CCCN>C(Cl)Cl.CO>[NH2:17][C@@H:5]1[C@@H:4]([CH2:1][CH:2]=[CH2:3])[N:7]([C:8](=[C:13]([CH3:15])[CH3:14])[C:9]([O:11][CH3:12])=[O:10])[C:6]1=[O:16]

Participants

5

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 14581222methyl 2-[(3R,4R)-4-allyl-3-phthalimido-2-oxoazetidin-1-yl]-3-methyl-2-butenoate

Product 1

HCID 14581224methyl [(3R,4R)-3-amino-4-allyl-2-oxoazetidin-1-yl]-3-methylbut-2-enoateYield 84.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-[(3R,4R)-4-allyl-3-phthalimido-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (6.78 g) in a mixture of methylene chloride (46 ml) and methanol (23 ml) was added N,N-dimethyl-1,3-propanediamine (6.25 ml) at 0° C. and the mixture was left at room temperature for 5 days. The reaction mixture was evaporated and the residue was chromatographed on silica gel eluting with a mixture of methylene chloride and ethyl acetate (10:1-5) to give methyl 2-[(3R,4R)-3-amino-4-allyl-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (3.70 g) as an oil.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was chromatographed on silica gel eluting with a mixture of methylene chloride and ethyl acetate (10:1-5)

Sources & evidence

ORD record
ord-72fe25c17d5f42e8ac196941b03ef464
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

Loading…