反応 #2275710

反応方程式

glycine methyl ester hydrochloride

4-iodo-picolinic acid

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

1-hydroxybenzotriazole

→

desired product

収率 44.4%

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

収率 44.4%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   workup.STIRRINGthe reaction is stirred 16 hours
2. 2
   濃縮The reaction volume is concentrated under reduced pressure
3. 3
   その他the crude material was partitioned between EtOAc and 1M K2CO3
4. 4
   その他The aqueous phase is removed
5. 5
   洗浄the organic phase washed with H2O, sat. NaCl
6. 6
   乾燥dried (MgSO4)
7. 7
   ろ過filtered
8. 8
   濃縮concentrated under reduced pressure
9. 9
   その他to afford a brown oil which
10. 10
    その他is purified over silica (EtOAc:heptane gradient 1:4)

実験手順

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]+.

出典