Triethylamine → N-Benzoyl-3-azetidinone

HRID 371910Notes

Reaction equation

HRID 371910 reaction equation
[C:1]([N:9]1[CH2:12][CH:11]([OH:13])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.S(=O)(=O)=O.N1C=CC=CC=1>CS(C)=O>[C:1]([N:9]1[CH2:12][C:11](=[O:13])[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 20352194(3-hydroxyazetidin-1-yl)(phenyl)Methanone

Product 1

HCID 11105876N-Benzoyl-3-azetidinone

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred mixture of 2.5 g. of N-benzoyl-3-azetidinol, 21 g. of triethylamine in 35 ml. of DMSO, add rapidly, in a dropwise manner, a suspension of 7.0 g. of pyridine sulfur trioxide in 35 ml. of DMSO and stir for 15 minutes. Remove most of the DMSO in vacuo at 60° C and chromatograph the residue on 100 g. of silica gel. Elute with chlorform and collect 2.4 g. of the crude compound of this example from the front running yellow band. Recrystallize from isopropyl ether.

Workup

  1. additionTo a stirred mixture of 2.5 g
  2. additiona suspension of 7.0 g
  3. customRemove most of the DMSO in vacuo at 60° C
  4. washElute with chlorform
  5. customcollect 2.4 g
  6. customRecrystallize from isopropyl ether

Sources & evidence

ORD record
ord-4e3f69f9f85544f6b8fbf5cf32ae526d
Source dataset
uspto-grants-1978_05
Patent number
US04088644

Reaction notes

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