تفاعل #508777
ord-1d5ce1fa38924a47896df937bb8a33e6
معادلة التفاعل
المتفاعلات
الكواشف
المذيبات
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المعالجة
- 1درجة الحرارةThe mixture was chilled with an ice water bath
- 2أخرىThe crude reaction
- 3درجة الحرارةwas then chilled in an ice water bath
- 4ترشيحthe precipitate filtered
- 5غسيلThe resulting organic solution was then washed twice with 1N aqueous sodium hydroxide (50 mL), twice with 10% aqueous citric acid (50 mL)
- 6تجفيفThe solution was then dried over anhydrous sodium sulfate
- 7ترشيحfiltered
- 8أخرىthe solvent evaporated
- 9أخرىThe resulting residue was purified by chromatography on a normal phase silica gel column with 30-100% ethyl acetate in hexanes
- 10workup.ADDITIONFractions containing clean product
- 11أخرىthe solvent evaporated
الإجراء التجريبي
To a solution of Boc-alanine (20 grams, 105.7 mmol) in dichloromethane (170 ml) was added HOBT (14.28 g, 105.7 mmol) and N, O-dimethylhydroxylamine hydrochloride (10.31 g, 105.7 mmol). The mixture was chilled with an ice water bath then triethylamine (30 ml, 211.4 mmol) and 1,3-dicyclohexylcarbodiimide (21.81 g, 105.7 mmol) were added. The reaction was stirred in the ice water bath for 1 hour and then allowed to warm to room temperature overnight. The crude reaction was then chilled in an ice water bath and the precipitate filtered. The resulting organic solution was then washed twice with 1N aqueous sodium hydroxide (50 mL), twice with 10% aqueous citric acid (50 mL), and once with brine. The solution was then dried over anhydrous sodium sulfate, filtered, and the solvent evaporated. The resulting residue was purified by chromatography on a normal phase silica gel column with 30-100% ethyl acetate in hexanes. Fractions containing clean product were combined and the solvent evaporated to give the title compound (20 g, 81%): ES-MS (m/z) 233.2 [M+1]+.