تفاعل #802830

معادلة التفاعل

triethylamine

1,3-dicyclohexylcarbodiimide

Boc-alanine

HOBT

N,O-dimethylhydroxylamine hydrochloride

→

title compound

المردود 81.5%

(2S)-2-[(tert-Butoxy)carbonylamino]-N-methoxy-N-methylpropanamide

المردود 81.5%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was chilled with an ice water bath
2. 2
   أخرىThe crude reaction
3. 3
   درجة الحرارةwas then chilled in an ice water bath
4. 4
   ترشيحthe precipitate filtered
5. 5
   غسيلThe resulting organic solution was then washed twice with 1N aqueous sodium hydroxide (50 mL), twice with 10% aqueous citric acid (50 mL)
6. 6
   تجفيفThe solution was then dried over anhydrous sodium sulfate
7. 7
   ترشيحfiltered
8. 8
   أخرىthe solvent evaporated
9. 9
   أخرىThe resulting residue was purified by chromatography on a normal phase silica gel column with 30-100% ethyl acetate in hexanes
10. 10
    workup.ADDITIONFractions containing clean product
11. 11
    أخرىthe 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]+.

المصدر