Water → HCID 57116796, compound

HRID 1075641Notes

Reaction equation

HRID 1075641 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([NH:16][C@H:17]1[C@H:20]([O:21][C:22](=O)[CH3:23])[NH:19][C:18]1=[O:25])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:26]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]([C:14]([NH:16][C@H:17]1[C@@H:20]([O:21][CH2:22][CH2:23][Br:26])[NH:19][C:18]1=[O:25])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 962WaterHCID 108982-BromoethanolHCID 57305915HCID 57305915, compound

Product 1

HCID 57116796HCID 57116796, compoundYield 12%

Reagents, catalysts & solvents 3

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

Procedure

A mixture of (3S,4S)-3-(N-benzyloxycarbonyl-L-alanyl)amino-4-acetoxy-azetidin-2-one (1.36 g, 3.894 mmole), 2-bromoethanol (440 mg, 3.5 mmole), and zinc acetate dihydrate (642 mg, 2.9 mmole) in a mixture of benzene (40 ml) and toluene (40 ml) was refluxed for 5 hrs using Dean-Stark water separator. After cooling, the reaction mixture was partitioned between ethyl acetate (200 ml), acetone (25 ml) and water (150 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 (2:1) as eluent and (3S,4R)-3-(N-benzyloxycarbonyl-L-alanyl)amino-4-bromoethoxy-azetidin-2-one was obtained (169 mg, 12% yield).

Workup

  1. temperaturewas refluxed for 5 hrs
  2. temperatureAfter cooling
  3. customthe reaction mixture was partitioned between ethyl acetate (200 ml), acetone (25 ml) and water (150 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-221e899a258b4b78981389fc7e97084a
Source dataset
uspto-grants-1999_05
Patent number
US05905076

Reaction notes

Loading…