Reaktion #2275710

Reaktionsgleichung

glycine methyl ester hydrochloride

4-iodo-picolinic acid

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

1-hydroxybenzotriazole

→

desired product

Ausbeute 44.4%

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

Ausbeute 44.4%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction is stirred 16 hours
2. 2
   EinengenThe reaction volume is concentrated under reduced pressure
3. 3
   Sonstigethe crude material was partitioned between EtOAc and 1M K2CO3
4. 4
   SonstigeThe aqueous phase is removed
5. 5
   Waschenthe organic phase washed with H2O, sat. NaCl
6. 6
   Trocknendried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated under reduced pressure
9. 9
   Sonstigeto afford a brown oil which
10. 10
    Sonstigeis purified over silica (EtOAc:heptane gradient 1:4)

Vorschrift

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]+.

Quelle