반응 #1753219
ord-02f55ea4b9014151b06c6b99a89e175b
반응 방정식
반응물
시약
반응 조건
후처리
- 1기타was adjusted to 35° C
- 2workup.ADDITIONwas added dropwise over 2 hours
- 3기타The reaction mixture was further reacted for 4.5 hours
- 4기타to obtain a reaction solution
- 5workup.ADDITIONwas added
- 6추출was then extracted with ethyl acetate
- 7세척The organic layer was washed with saturated saline
- 8농축concentrated
- 9기타to obtain residues
- 10기타The residues were subjected to recrystallization from 60 ml of 28% ammonia water and 1350 ml of 2-propanol
실험 절차
73.8 g (352 mmol) of indol-3-pyruvic acid was added to and dissolved in 917 g of 1.6 wt % aqueous sodium hydroxide. The temperature of the reaction solution was adjusted to 35° C. While the pH of the solution was kept at 11.1 with 30% aqueous sodium hydroxide, 310.2 g (1761 mmol) of 50% aqueous pyruvic acid was added dropwise over 2 hours. The reaction mixture was further reacted for 4.5 hours to obtain a reaction solution containing 4-hydroxy-4-(3-indolylmethyl)-2-ketoglutaric acid. While the pH of this reaction solution was kept at 7 with 30% aqueous sodium hydroxide, 367.2 g (2114 mmol) of 40% aqueous hydroxylamine hydrochloride was added thereto, and the mixture was stirred at 5° C. for 17.5 hours. The pH value of the reaction solution was adjusted to 2 with concentrated hydrochloric acid, and its organic matter was then extracted with ethyl acetate. The organic layer was washed with saturated saline and then concentrated to obtain residues. The residues were subjected to recrystallization from 60 ml of 28% ammonia water and 1350 ml of 2-propanol to obtain 43.4 g of 4-hydroxy-4-(3-indolylmethyl)-2-hydroxyiminoglutarate diammonium salt (142 mmol: yield 40% relative to indol-3-pyruvic acid) as crystals.