Reaction #2275710

Reaction equation

glycine methyl ester hydrochloride

4-iodo-picolinic acid

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

1-hydroxybenzotriazole

→

desired product

Yield 44.4%

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

Yield 44.4%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   workup.STIRRINGthe reaction is stirred 16 hours
2. 2
   ConcentrationThe reaction volume is concentrated under reduced pressure
3. 3
   Otherthe crude material was partitioned between EtOAc and 1M K2CO3
4. 4
   OtherThe aqueous phase is removed
5. 5
   Washthe organic phase washed with H2O, sat. NaCl
6. 6
   Dryingdried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated under reduced pressure
9. 9
   Otherto afford a brown oil which
10. 10
    Otheris purified over silica (EtOAc:heptane gradient 1:4)

Procedure

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]+.

Source