Реакция #1876806

Уравнение реакции

lithium hydroxide monohydrate

methyl 3-(5-tert.butoxycarbonylamino-2-ethoxymethoxyphenyl)acrylate

phosphate

→

3-(5-tert.butoxycarbonylamino-2-ethoxymethoxyphenyl)acrylic acid

Растворители

tetrahydrofuran

methanol

water

Условия реакции

Обработка

1. 1
   Экстракцияextracted with ethyl acetate
2. 2
   Промывкаthe organic phase was washed with a saturated aqueous sodium chloride solution
3. 3
   Сушкаdried over sodium sulfate
4. 4
   ДругоеThe organic phase was partially evaporated to incipient formation of a precipitate, and hexane
5. 5
   workup.ADDITIONwas then added
6. 6
   ФильтрацияThe precipitate was filtered off
7. 7
   Промывкаwashed with 50 mL of hexane

Методика

2.53 g (0.06 mol) of lithium hydroxide monohydrate was added at 0° C. to a solution of 6.3 g (0.018 mol) of methyl 3-(5-tert.butoxycarbonylamino-2-ethoxymethoxyphenyl)acrylate from step D in 50 mL of tetrahydrofuran, 15 mL of methanol and 30 mL of water. The mixture was allowed to agitate 24 hours at 60° C. The reaction mixture was then poured onto a phosphate buffer solution (pH 7.0) and extracted with ethyl acetate, and the organic phase was washed with a saturated aqueous sodium chloride solution and then dried over sodium sulfate. The organic phase was partially evaporated to incipient formation of a precipitate, and hexane was then added. The precipitate was filtered off and washed with 50 mL of hexane. This gave 5.4 g (89% of the theoretical) of 3-(5-tert.butoxycarbonylamino-2-ethoxymethoxyphenyl)acrylic acid.

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