Compound containing guanidyl group, and preparation method and application thereof
A compound and guanidine-based technology, applied in the field of preparation of the compound, method and intermediate, can solve the problems of limited curative effect and high cost
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Embodiment 1
[0122] Example 1: Ethyl (2S)-2-(chloro(phenoxy)phosphorylamino)propionate (chloride A1)
[0123]
[0124] Ethylalaninate hydrochloride (2.54g, 16.5mmol) was dissolved in anhydrous dichloromethane (30ml) and the mixture was cooled to 0°C with stirring under N2 (g). Phenyl dichlorophosphate (2.23 mL, 25 mmol) was added, followed by the dropwise addition of triethylamine over 10 min. The reaction mixture was then slowly warmed to RT and stirred for 12 h. Anhydrous acetic anhydride (150 mL) was added, and the mixture was stirred for 30 min. The solid formed was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was chromatographed on silica gel eluting with 0-50% EtOAc in hexanes to provide chloride Al (1.86 g, 39%).
[0125] 1 H NMR (300 MHz, CDC13) δ 7.39-7.27 (m, 5H), 4.27 (m, 3H), 1.52 (m, 3H), 1.32 (m, 3H).
[0126] 31 P NMR (121.4MHz, CDCl 3 )δ8.2,7.8.
Embodiment 2
[0127] Example 2: 9-ethylbutyl (2S)-2-(chloro(phenoxy)phosphorylamino)propionate (chloride B1)
[0128]
[0129] 2-Ethylbutylalanine chlorophosphoramidate B1 was prepared using the same procedure as chloride A1 except that 2-ethylbutylalanine was used instead of ethylalanine. The crude material was used in the next reaction. Treatment with methanol or ethanol forms a surrogate product with the desired LCMS signal.
Embodiment 3
[0130] Example 3: Isopropyl (2S)-2-(chloro(phenoxy)phosphorylamino)propionate (chloride C1)
[0131]
[0132] Isopropylalanine chlorophosphoramidate C1 was prepared using the same procedure as chloride A1 except that isopropylalanine was used instead of ethylalanine. The crude material was used in the next reaction. Treatment with methanol or ethanol forms a surrogate product with the desired LCMS signal.
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