Water → HCID 57228824, compound

HRID 1075643Notes

Reaction equation

HRID 1075643 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([NH:22][C@H:23]1[C@H:26]([O:27][C:28](=O)[CH3:29])[NH:25][C:24]1=[O:31])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:32]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:20]([NH:22][C@H:23]1[C@H:26]([O:27][CH2:28][CH2:29][Br:32])[NH:25][C:24]1=[O:31])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 962WaterHCID 108982-BromoethanolHCID 15547238HCID 15547238, compound

Product 1

HCID 57228824HCID 57228824, compoundYield 12%

Reagents, catalysts & solvents 3

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

Procedure

A mixture of (3S,4S)-3-(N-benzyloxycarbonyl-L-phenylalanyl)amino-4-acetoxy-azetidin-2-one (4.57 g, 10.8 mmole), 2-bromoethanol (1479 mg, 11.83 mmole), and zinc acetate dihydrate (1.78 g, 8.128 mmole) in a mixture of benzene (150 ml) and toluene (150 ml) was refluxed for 7 hrs using Dean-Stark water separator. After cooling, the reaction mixture was partitioned between ethyl acetate (1000 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 (55:45) as eluent and (3S,4S)-3-(N-benzyloxycarbonyl-L-phenylalanyl)amino-4-bromoethoxy-azetidin-2-one was obtained (650 mg, 12% yield).

Workup

  1. temperaturewas refluxed for 7 hrs
  2. temperatureAfter cooling
  3. customthe reaction mixture was partitioned between ethyl acetate (1000 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-4a06891c0c36445f9405e64d7fd9f9bf
Source dataset
uspto-grants-1999_05
Patent number
US05905076

Reaction notes

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