Reacción #2275710

Ecuación de reacción

glycine methyl ester hydrochloride

4-iodo-picolinic acid

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

1-hydroxybenzotriazole

→

desired product

Rendimiento 44.4%

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

Rendimiento 44.4%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction is stirred 16 hours
2. 2
   ConcentraciónThe reaction volume is concentrated under reduced pressure
3. 3
   Otrothe crude material was partitioned between EtOAc and 1M K2CO3
4. 4
   OtroThe aqueous phase is removed
5. 5
   Lavadothe organic phase washed with H2O, sat. NaCl
6. 6
   Secadodried (MgSO4)
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated under reduced pressure
9. 9
   Otroto afford a brown oil which
10. 10
    Otrois purified over silica (EtOAc:heptane gradient 1:4)

Procedimiento

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]+.

Fuente