Methanol → HCID 54411637, compound

HRID 1706525Notes

Reaction equation

HRID 1706525 reaction equation
C1(=O)[N:5]([CH:6]2[CH2:9][N:8]([CH:10]([C:17]([OH:19])=[O:18])[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:7]2=[O:20])C(=O)C2=CC=CC=C12.CN(C)CCCN.CO>O>[NH2:5][CH:6]1[CH2:9][N:8]([CH:10]([C:17]([OH:19])=[O:18])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]1=[O:20]

Participants

5

Reactant 3

HCID 887MethanolHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 54250743HCID 54250743, compound

Product 1

HCID 54411637HCID 54411637, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Phthalimido-1-(α-carboxybenzyl)-2-azetidinone (350 mg.) and N,N-dimethyl-1,3-propanediamine (310 mg.) were added to methanol (6 ml.), and the mixture was stirred at ambient temperature for 18 hours. Water (6 ml.) was poured into the reaction mixture under ice-cooling and then the mixture was adjusted to pH 5.8 to 6.0 with cation-exchange resin IRC-50 (Trade Mark, maker: Rohm & Haas Co.,) (20 ml.). The resin was removed by filtration and the filtrate was evaporated to dryness under reduced pressure. Acetonitrile was added to the residue (190 mg.) obtained and then the mixture was stirred under ice-cooling for 2.5 hours. The powder was collected by filtration to give 3-amino-1-(α-carboxybenzyl)-2-azetidinone (120 mg.).

Workup

  1. temperaturecooling
  2. customThe resin was removed by filtration
  3. customthe filtrate was evaporated to dryness under reduced pressure
  4. additionAcetonitrile was added to the residue (190 mg.)
  5. customobtained
  6. stirringthe mixture was stirred under ice-
  7. temperaturecooling for 2.5 hours
  8. filtrationThe powder was collected by filtration

Sources & evidence

ORD record
ord-71197dde664c48c1a49656dcc9137487
Source dataset
uspto-grants-1980_06
Patent number
US04207234

Reaction notes

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