Water → HCID 70093772, compound

HRID 1603249Notes

Reaction equation

HRID 1603249 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([C@@H:22]1[C@H:25](OC(=O)C)[N:24]([NH2:30])[C:23]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.[C:32]1([SH:38])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.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]([C@H:22]1[C@H:25]([S:38][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:24]([NH2:30])[C:23]1=[O:31])=[O:21])[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 962WaterHCID 7969ThiophenolHCID 70093171HCID 70093171, compound

Product 1

HCID 70093772HCID 70093772, compoundYield 80.6%

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 (500 mg, 1.18 mmol) obtained in example 7, thiophenol (117 mg, 1.07 mmol), and zinc acetate dihydrate (207 mg, 0.95 mmol) in a mixture of benzene (20 ml) and toluene (20 ml) was refluxed for 4 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 the solvent to dryness, a white solid was washed with dichloromethane and 410 mg of the title compound was obtained as a white solid.

Workup

  1. temperaturewas refluxed for 4 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 the solvent to dryness
  8. washa white solid was washed with dichloromethane

Sources & evidence

ORD record
ord-51f5502e8fa5477cb0d46209264be8e0
Source dataset
uspto-grants-1999_11
Patent number
US05986108

Reaction notes

Loading…