Ethyl Acetate → HCID 20445629, compound

HRID 1706536Notes

Reaction equation

HRID 1706536 reaction equation
C1(=O)[N:5]([CH:6]2[CH2:9][N:8]([CH2:10][C:11]([O-:13])=[O:12])[C:7]2=[O:14])C(=O)C2=CC=CC=C12.O.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.C(OCC)(=O)C>C(Cl)(Cl)Cl.C(O)C>[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28]([OH:12])(=[O:30])=[O:29])=[CH:24][CH:23]=1.[NH2:5][CH:6]1[CH2:9][N:8]([CH2:10][C:11]([O:13][CH2:32][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:12])[C:7]1=[O:14]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 20445626HCID 20445626, compoundHCID 21708529HCID 21708529, compound

Product 1

HCID 20445629HCID 20445629, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent5×HCID 6212ChloroformSolvent

Procedure

2-(3phthalimido-2-oxo-1-azetidinyl)acetate was dissolved in a mixture (5 ml.) of chloroform and ethanol (1:1), and 1N ethanol solution of hydrozene monohydrate (1ml.) was added thereto at ambient temperature while stirring. The stirring was continued for 72 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue thus obtained was dissolved in ethanol, and then ethanol solution (1 ml.) of p-toluenesulfonyl chloride monohydrate (190 mg.) was added thereto. The mixture was concentrated under reduced pressure, and to the residue thus obtained there were added ethanol (1 ml.) and ethyl acetate (2 ml.) to give crystalline benzyl 2-(3-amino-2-oxo-1-azetidinyl)acetate p-toluenesulfonic acid salt, mp 147.5°-149° C.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue thus obtained
  5. concentrationThe mixture was concentrated under reduced pressure
  6. customto the residue thus obtained there

Sources & evidence

ORD record
ord-2b7992858927430f97fc2375487528ca
Source dataset
uspto-grants-1980_06
Patent number
US04207234

Reaction notes

Loading…