Реакция #213874

Уравнение реакции

methyl ester

3-Carbomethoxymethyl-4-oxo-5-phthalimido-1,3-thiazine

tetrahydrofuran

hydrochloric acid

→

3-Carboxymethyl-4-oxo-5-phthalimido-1,3-thiazine

Растворители

water

Условия реакции

Обработка

1. 1
   ТемператураThe solution was cooled
2. 2
   workup.ADDITIONdiluted with 5 ml
3. 3
   Экстракцияof water and then extracted four times with a total of 15 ml
4. 4
   СушкаThe organic phase was dried over sodium sulfate
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   ДругоеThe resulting residue was triturated with dichloromethane and crystals
7. 7
   Другоеformed
8. 8
   Промывкаwhich were washed with dichloromethane
9. 9
   Другоеdried
10. 10
    Другоеto give 10.1 mg
11. 11
    КонцентрированиеThe mother liquor on concentration in vacuo
12. 12
    Другоеalso crystallized
13. 13
    Другоеto give 13.3 mg

Методика

A 24 mg. (0.07 mmole) sample of the methyl ester product obtained in Step A. above, in a solution of 1.5 ml. of tetrahydrofuran, 0.5 ml. of water, and 0.25 ml. of concentrated hydrochloric acid, was refluxed under nitrogen for 3.5 hrs. The solution was cooled and diluted with 5 ml. of water and then extracted four times with a total of 15 ml. of dichloromethane. The organic phase was dried over sodium sulfate and concentrated in vacuo. The resulting residue was triturated with dichloromethane and crystals formed, which were washed with dichloromethane and dried to give 10.1 mg. of product having a m.p. of 227°-228° C. The mother liquor on concentration in vacuo also crystallized to give 13.3 mg. of product.

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