Ammonium Chloride → HCID 67743997, compound

HRID 904996Notes

Reaction equation

HRID 904996 reaction equation
[CH3:1][Mg]Cl.[O:4]([CH2:11][C:12]([NH:14][C@H:15]1[C@H:18](S(C2C=CC=CC=2)(=O)=O)[NH:17][C:16]1=[O:28])=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl-].[NH4+]>[Cl-].[Cl-].[Mg+2].O1CCCC1>[O:4]([CH2:11][C:12]([NH:14][C@H:15]1[C@@H:18]([CH3:1])[NH:17][C:16]1=[O:28])=[O:13])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 11024808HCID 11024808, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 67743997HCID 67743997, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 5360315Magnesium ChlorideSolvent

Conditions

Temperature
-10 °C

Procedure

Methyl magnesium chloride (2.9 ml, of 2.9 M in tetrahydrofuran) was added to a solution of 500 mg (3R-trans)-3-phenoxyacetylamino-4-phenylsulfonyl-2-azetidinone in 11.1 ml of 0.5 M magnesium dichloride in tetrahydrofuran under nitrogen and chilled in an ice/acetone bath (-10° C.). After 2 hours, the mixture was added to saturated aqueous ammonium chloride and extracted with ethyl acetate. The extract was washed with water, dried over sodium sulfate, and evaporated. Treatment of the residue with dichloromethane/ethyl ether gave 106 mg of cis-3-phenoxyacetylamino-4-methyl-2-azetidinone. The corresponding trans isomer, as well as some cis isomer, was present in the mother liquor, as shown by NMR.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-0367e442cc00439494c7e41159036afa
Source dataset
uspto-grants-1983_12
Patent number
US04421686

Reaction notes

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