Water → HCID 15858810, compound

HRID 1075635Notes

Reaction equation

HRID 1075635 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@H:15]([O:16][C:17](=O)[CH3:18])[NH:14][C:13]1=[O:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:21]CCO.O>C1C=CC=CC=1.C1(C)C=CC=CC=1.O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@@H:15]([O:16][CH2:17][CH2:18][Br:21])[NH:14][C:13]1=[O:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 962WaterHCID 108982-BromoethanolHCID 13124491HCID 13124491, compound

Product 1

HCID 15858810HCID 15858810, compoundYield 14.1%

Reagents, catalysts & solvents 3

HCID 2724192Zinc acetate (USP)CatalystHCID 241BenzeneSolventHCID 1140TolueneSolvent

Procedure

A mixture of (3S,4S)-3-benzyloxycarbonylamino-4-acetoxy-azetidin-2-one (11.76 g, 42.3 mmole) which prepared by the known method (Eur. J. Med. Chem. 1992, 27, 131-140), 2-bromoethanol (3 ml, 42.3 mmole), and zinc acetate dihydrate (9.28 g, 42.3 mmole) in a mixture of benzene (100 ml) and toluene (100 ml) was refluxed for 5 hrs using Dean-Stark water separator. After cooling, the reaction mixture was partitioned between ethyl acetate (800 ml), acetone (100 ml) and water (500 ml). The organic layer was washed with water, brine and dried over sodium sulfate. After removal of the solvent, the residue was purified by silica gel column chromatography using ethyl acetate-hexane (6:4) as eluent and 2.04 g of (3S,4R)-3-benzyloxycarbonylamino-4-bromoethoxy-azetidin-2-one was obtained as white solid (yield: 14%).

Workup

  1. temperaturewas refluxed for 5 hrs
  2. temperatureAfter cooling
  3. customthe reaction mixture was partitioned between ethyl acetate (800 ml), acetone (100 ml) and water (500 ml)
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of the solvent
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-95323b021a324b97825165e140d02a79
Source dataset
uspto-grants-1999_05
Patent number
US05905076

Reaction notes

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