تفاعل #2275710

معادلة التفاعل

glycine methyl ester hydrochloride

4-iodo-picolinic acid

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

1-hydroxybenzotriazole

→

desired product

المردود 44.4%

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

المردود 44.4%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe reaction is stirred 16 hours
2. 2
   تركيزThe reaction volume is concentrated under reduced pressure
3. 3
   أخرىthe crude material was partitioned between EtOAc and 1M K2CO3
4. 4
   أخرىThe aqueous phase is removed
5. 5
   غسيلthe organic phase washed with H2O, sat. NaCl
6. 6
   تجفيفdried (MgSO4)
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated under reduced pressure
9. 9
   أخرىto afford a brown oil which
10. 10
    أخرىis purified over silica (EtOAc:heptane gradient 1:4)

الإجراء التجريبي

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]+.

المصدر