تفاعل #1282
ord-6edcc2e8e3744c608ae582a2c614eb39
معادلة التفاعل
المتفاعلات
الكواشف
ظروف التفاعل
المعالجة
- 1ترشيحfiltered
- 2أخرىfiltrate evaporated to dryness
- 3أخرىagain evaporated to dryness
- 4أخرىplaced in an ice bath
- 5أخرىthe mixture was partitioned between ethyl acetate-5% potassium bisulfate
- 6غسيلThe organic phase was washed successively with 5% potassium bisulfate, saturated sodium bicarbonate and saturated sodium chloride solutions
- 7تجفيفdried (sodium sulfate)
- 8أخرىevaporated to dryness
- 9أخرىPurification of the crude product by flash chromatography on silica gel (Whatmann LPS-1)
- 10غسيلeluting with ethyl acetate:hexane (1:2)
- 11أخرىgave 1.0747 g
- 12أخرىA sample crystallized from hexane
- 13أخرى[α]D =+87.2° (C=0.53, chloroform)
الإجراء التجريبي
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).