반응 #2275710

반응 방정식

glycine methyl ester hydrochloride

4-iodo-picolinic acid

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

1-hydroxybenzotriazole

→

desired product

수율 44.4%

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

수율 44.4%

용매

CH2Cl2

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction is stirred 16 hours
2. 2
   농축The reaction volume is concentrated under reduced pressure
3. 3
   기타the crude material was partitioned between EtOAc and 1M K2CO3
4. 4
   기타The aqueous phase is removed
5. 5
   세척the organic phase washed with H2O, sat. NaCl
6. 6
   건조dried (MgSO4)
7. 7
   여과filtered
8. 8
   농축concentrated under reduced pressure
9. 9
   기타to afford a brown oil which
10. 10
    기타is purified over silica (EtOAc:heptane gradient 1:4)

실험 절차

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]+.

출처