Реакция #2005504

Уравнение реакции

O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate

2-amino-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester

4-methoxy-3-(2-m-tolyl-ethoxy)-benzoic acid

→

title compound

Выход 100.1%

2-[4-Methoxy-3-(2-m-tolyl-ethoxy)-benzoylamino]-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester

Выход 100.1%

Растворители

DMF

EA

Условия реакции

Обработка

1. 1
   Промывкаwashed three times with 50 ml each of a saturated aqueous sodium carbonate solution
2. 2
   СушкаThe organic layer was dried with magnesium sulfate
3. 3
   Другоеevaporated to dryness
4. 4
   Другоеthe residue purified by silica gel chromatography (HEP/EA gradient)

Методика

550 mg of O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU), 300 mg of 2-amino-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester and 410 mg of 4-methoxy-3-(2-m-tolyl-ethoxy)-benzoic acid (example 2) were stirred in 20 ml of anhydrous DMF for 15 h at room temperature. The mixture was diluted with 150 ml of EA and washed three times with 50 ml each of a saturated aqueous sodium carbonate solution and then three times with 50 ml each of a 10% aqueous sodium hydrogensulfate solution. The organic layer was dried with magnesium sulfate, evaporated to dryness and the residue purified by silica gel chromatography (HEP/EA gradient) to yield 630 mg of the title compound as a racemic mixture.

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