Реакция #2275710

Уравнение реакции

glycine methyl ester hydrochloride

4-iodo-picolinic acid

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

1-hydroxybenzotriazole

→

desired product

Выход 44.4%

[(4-iodo-pyridine-2-carbonyl)-amino]-acetic acid methyl ester

Выход 44.4%

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe reaction is stirred 16 hours
2. 2
   КонцентрированиеThe reaction volume is concentrated under reduced pressure
3. 3
   Другоеthe crude material was partitioned between EtOAc and 1M K2CO3
4. 4
   ДругоеThe aqueous phase is removed
5. 5
   Промывкаthe organic phase washed with H2O, sat. NaCl
6. 6
   Сушкаdried (MgSO4)
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated under reduced pressure
9. 9
   Другоеto afford a brown oil which
10. 10
    Другоеis purified over silica (EtOAc:heptane gradient 1:4)

Методика

To a solution of 4-iodo-picolinic acid (1.41 g, 5.66 mmol) in CH2Cl2 (35 mL) at room temperature under N2 is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI) (1.62 g, 8.49 mmol) and 1-hydroxybenzotriazole (HOBt) (0.077 g, 0.57 mmol). The solution is stirred for 5 minutes and glycine methyl ester hydrochloride (1.07 g, 8.49 mmol) is added and the reaction is stirred 16 hours. The reaction volume is concentrated under reduced pressure and the crude material was partitioned between EtOAc and 1M K2CO3. The aqueous phase is removed and the organic phase washed with H2O, sat. NaCl, dried (MgSO4), filtered and concentrated under reduced pressure to afford a brown oil which is purified over silica (EtOAc:heptane gradient 1:4) to afford 0.805 g (44% yield) of the desired product as a colorless solid. HPLC-MS: m/z 321 [M+H]+.

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