Dichloromethane → HCID 15592309, compound

HRID 27808Notes

Reaction equation

HRID 27808 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[CH2:14][N:13]([CH:15]([C:23]([O:25]CC3C=CC=CC=3)=[O:24])[C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[C:12]2=[O:33])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-].C1(OC)C=CC=CC=1>C(OCC)(=O)C>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[CH2:14][N:13]([CH:15]([C:23]([OH:25])=[O:24])[C:16]3[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=3)[C:12]2=[O:33])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 53982386HCID 53982386, compound

Product 1

HCID 15592309HCID 15592309, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-phenylacetamido-1-(α-carbobenzoxy-p-hydroxybenzyl) azetidin-2-one (15 mg), methylene chloride (0.5 ml), aluminum chloride (12 mg) and anisole (0.2 ml) is kept at -20° C. for 8 hours. The reaction mixture is diluted with ethyl acetate, washed with dilute hydrochloric acid and water, dried, and concentrated in vacuo. Crystallizing the residue from a mixture of ethyl acetate and ether gives 3-phenylacetamido-1-(α-carboxy-p-hydroxybenzyl)azetidin-2-one (9 mg) melting at 134°-141° C. Yield: 75%.

Workup

  1. washwashed with dilute hydrochloric acid and water
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customCrystallizing the residue
  5. additionfrom a mixture of ethyl acetate and ether

Sources & evidence

ORD record
ord-5fb5ffb3a35d46309d0b038e9ba04a48
Source dataset
uspto-grants-1980_09
Patent number
US04223132

Reaction notes

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