Реакция #330141

Уравнение реакции

N2-phenylpyridine-2,3-diamine

(S)-2-tertbutoxycarbonylamino-3-methylbutyric acid

HOAt

4-methylmorpholine

N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride

→

[(S)-2-methyl-1-(2-phenylaminopyridin-3-ylcarbamoyl)propyl]carbamic acid tert-butyl ester

Растворители

DCM

Условия реакции

Обработка

1. 1
   ДругоеThe reaction mixture was partitioned between DCM
2. 2
   ПромывкаThe organic layer was washed with brine
3. 3
   Сушкаdried (MgSO4)
4. 4
   Концентрированиеconcentrated in vacuo
5. 5
   Другоеthe resulting residue purified by column chromatography (Si—PCC, gradient 0-30% EtOAc in cyclohexane)

Методика

A mixture of N2-phenylpyridine-2,3-diamine (556 mg, 3.0 mmol), (S)-2-tertbutoxycarbonylamino-3-methylbutyric acid (0.72 g, 3.3 mmol), HOAt (0.450 g, 3.3 mmol), 4-methylmorpholine (0.73 mL, 6.6 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.63 g, 3.3 mmol) in DCM (15 mL) was stirred at RT for 18 h. The reaction mixture was partitioned between DCM and a saturated aqueous solution of NaHCO3. The organic layer was washed with brine, dried (MgSO4), concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-30% EtOAc in cyclohexane) to afford [(S)-2-methyl-1-(2-phenylaminopyridin-3-ylcarbamoyl)propyl]carbamic acid tert-butyl ester as a white solid (1.13 g, quantitative).

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