Dichloromethane → HCID 11024808, compound

HRID 904995Notes

Reaction equation

HRID 904995 reaction equation
[NH2:1][CH:2]1[CH:5]([S:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:8])=[O:7])[NH:4][C:3]1=[O:15].C(=O)(O)[O-].[Na+].ClCCl.[O:24]([CH2:31][C:32](Cl)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[O:24]([CH2:31][C:32]([NH:1][C@H:2]1[C@H:5]([S:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:8])=[O:7])[NH:4][C:3]1=[O:15])=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 69703Phenoxyacetyl chlorideHCID 516892Sodium BicarbonateHCID 54318832HCID 54318832, compound

Product 1

HCID 11024808HCID 11024808, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice-cooled mixture of 7.6 g of 3-amino-4-phenylsulfonyl-2-azetidinone (mixture of cis and trans isomers), 5.1 g of sodium bicarbonate 100 ml of dichloromethane, and 50 ml of water was added dropwise with vigorous stirring 4.0 ml phenoxyacetyl chloride. After 90 minutes the resulting solid was removed by filtration and washed with water and dichloromethane. The solid was dissolved in tetrahydrofuran and precipitated with toluene to give 3.85 g of (3R-trans)-3-phenoxyacetylamino-4-phenylsulfonyl-2-azetidinone, melting point 192°-193° C., dec.

Workup

  1. additionwas added dropwise
  2. customAfter 90 minutes the resulting solid was removed by filtration
  3. washwashed with water and dichloromethane
  4. dissolutionThe solid was dissolved in tetrahydrofuran
  5. customprecipitated with toluene

Sources & evidence

ORD record
ord-afe803e57e7348d188936a64c9d3f156
Source dataset
uspto-grants-1983_12
Patent number
US04421686

Reaction notes

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