2-Mesitylenesulfonyl chloride → Benzyl N-[methyl(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)phosphoryl]glycinate

HRID 1084802Notes

Reaction equation

HRID 1084802 reaction equation
[C:1]1([C:7]2[CH2:11][CH:10]([P:12]([CH3:15])(=[O:14])O)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=C(C)C=C(C)C=1S(Cl)(=O)=O.N1C=NN=N1.C1(C)C(S(O)(=O)=O)=CC=CC=1.[CH2:45]([O:52][C:53](=[O:56])[CH2:54][NH2:55])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.S(=O)(=O)(O)[O-].[K+]>N1C=CC=CC=1.O>[CH2:45]([O:52][C:53](=[O:56])[CH2:54][NH:55][P:12]([CH:10]1[O:9][N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:11]1)([CH3:15])=[O:14])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

8

Reactant 5

HCID 130462-Mesitylenesulfonyl chlorideHCID 516920Potassium bisulfateHCID 3079447Methyl(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)phosphinic acidHCID 86744709HCID 86744709, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 3079446Benzyl N-[methyl(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)phosphoryl]glycinate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

1.1 g (5 mmol) of 3-phenyl-2-isoxazolin-5-yl(P-methyl)phosphinic acid are dissolved in 20 ml of pyridine and, while cooling in ice, 1.5 g (7 mmol) of mesitylsulfonyl chloride and 0.5 g (7 mmol) of tetrazole are added, and the mixture is then stirred at room temperature for 30 minutes. 1.7 g (5 mmol) of glycine benzyl ester toluenesulfonate are added, and stirring at room temperature is continued with the course of the reaction being followed by thin-layer chromatography. After the reaction is complete, water and half-concentrated potassium bisulfate solution are added to pH 2, the mixture is extracted three times with dichloromethane, and the organic phase is washed with water, dried and concentrated. The pure product is obtained with a melting point of 132° to 135° C. by chromatography on silica gel with dichloromethane/methanol mixtures as mobile phases.

Workup

  1. temperaturewhile cooling in ice
  2. stirringstirring at room temperature
  3. extractionthe mixture is extracted three times with dichloromethane
  4. washthe organic phase is washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe pure product is obtained with a melting point of 132° to 135° C. by chromatography on silica gel with dichloromethane/methanol mixtures as mobile phases

Sources & evidence

ORD record
ord-4f71953cceab4a4e93adaed495052897
Source dataset
uspto-grants-1991_04
Patent number
US05006515

Reaction notes

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