Benzyl Alcohol → HCID 86754558, compound

HRID 619706Notes

Reaction equation

HRID 619706 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([NH:11][C@H:12]([C:24]([C@@H:26]2[C@H:29](OC(=O)C)[N:28]([NH2:34])[C:27]2=[O:35])=[O:25])[CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:36]([OH:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.O>C1C=CC=CC=1.C1(C)C=CC=CC=1.O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[C:1]1([CH2:7][CH2:8][C:9]([NH:11][C@H:12]([C:24]([C@@H:26]2[CH:29]([O:43][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[N:28]([NH2:34])[C:27]2=[O:35])=[O:25])[CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 244Benzyl AlcoholHCID 962WaterHCID 86754559HCID 86754559, compound

Product 1

HCID 86754558HCID 86754558, compoundYield 23%

Reagents, catalysts & solvents 3

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

Procedure

A mixture of (3S,4S)-3{N-(3-phenylpropionoyl)-β-(2-naphthyl)-L-alanyl}-amino-4-acetoxy-azetidin-2-one (236 mg, 0.5 mmol), benzyl alcohol (54 mg, 0.5 mmol), and zinc acetate dihydrate (110 mg, 0.5 mmol) in benzene (20 ml) and toluene (20 ml) was refluxed for 5 hrs using Dean-Stark water separator. After cooling, the reaction mixture was partitioned between ethyl acetate, containing a small volume of acetone, and water. The organic layer was washed with water, brine and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography using hexane-ethyl acetate (1:1) as eluent and the title compound was obtained.

Workup

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

Sources & evidence

ORD record
ord-29a2617612fd4256975af8bb933e04fd
Source dataset
uspto-grants-1999_09
Patent number
US05959123

Reaction notes

Loading…