反応 #1282
ord-6edcc2e8e3744c608ae582a2c614eb39
反応方程式
反応物
試薬
反応条件
後処理
- 1ろ過filtered
- 2その他filtrate evaporated to dryness
- 3その他again evaporated to dryness
- 4その他placed in an ice bath
- 5その他the mixture was partitioned between ethyl acetate-5% potassium bisulfate
- 6洗浄The organic phase was washed successively with 5% potassium bisulfate, saturated sodium bicarbonate and saturated sodium chloride solutions
- 7乾燥dried (sodium sulfate)
- 8その他evaporated to dryness
- 9その他Purification of the crude product by flash chromatography on silica gel (Whatmann LPS-1)
- 10洗浄eluting with ethyl acetate:hexane (1:2)
- 11その他gave 1.0747 g
- 12その他A sample crystallized from hexane
- 13その他[α]D =+87.2° (C=0.53, chloroform)
実験手順
A solution of (S)-1,3,4,5-tetrahydro-4-phthalimido-3-oxo-2H-2-benzazepine-2-acetic acid, ethyl ester (1.67 g., 4.26 mmol.) in 1.0M hydrazine hydrate in ethanol (9.0 ml., 9.0 mmol.) was stirred at room temperature under argon for 36 hours. The mixture was diluted with an equal volume of ethyl acetate, filtered and filtrate evaporated to dryness. The residue was taken up in toluene and again evaporated to dryness. The colorless, semi-solid residue (1.81 g.) was taken up in dry methylene chloride (20 ml.), placed in an ice bath and treated successively with triethylamine (0.80 ml., 5.8 mmol.) and benzylchloroformate (0.77 ml., 5.4 mmol.). After stirring at 0° C. for 2 hours, the mixture was partitioned between ethyl acetate-5% potassium bisulfate. The organic phase was washed successively with 5% potassium bisulfate, saturated sodium bicarbonate and saturated sodium chloride solutions, dried (sodium sulfate), and evaporated to dryness. Purification of the crude product by flash chromatography on silica gel (Whatmann LPS-1) eluting with ethyl acetate:hexane (1:2) gave 1.0747 g. of product as a colorless foam; Rf =0.52 (ethyl acetate:toluene, 3:7). A sample crystallized from hexane had m.p. 80°-82° C.; [α]D =+87.2° (C=0.53, chloroform).