반응 #1756953

반응 방정식

2-methyl-4-oxo-4H-chromene-8-carbaldehyde

2,4-pentanedione

(3S)-1-benzyl-2,5-dioxopyrrolidin-3-yl (2E)-3-aminobut-2-enoate

→

desired product

(3S)-1-Benzyl-2,5-dioxopyrrolidin-3-yl (4R)-5-acetyl-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carboxylate

용매

2-propanol

반응 조건

후처리

1. 1
   온도heated
2. 2
   기타The solvent is removed in vacuo
3. 3
   기타the residue is purified by preparative HPLC

실험 절차

1 g (5.32 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde is introduced into 25 ml of 2-propanol and heated under reflux with 0.93 g (9.3 mmol) of 2,4-pentanedione and 1.53 g (5.32 mmol) of (3S)-1-benzyl-2,5-dioxopyrrolidin-3-yl (2E)-3-aminobut-2-enoate [preparation analogous to D. Alker et al., Eur. J. Med. Chem. 26 (9), 907-913 (1991), starting from (3S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione] overnight. The solvent is removed in vacuo, and the residue is purified by preparative HPLC. 950 mg (33% of theory) of the desired product are obtained as 4R/4S diastereomer mixture.

출처