반응 #2275716

반응 방정식

3-hydroxypicolinic acid

diisopropylethylamine

1-(3-dimethyl-aminopropyl)-3-ethylcarbodiimide

EDCI

1-hydroxybenzotriazole

glycine tert-butyl ester HCl

→

desired compound

수율 22.0%

[(3-hydroxy-pyridine-2-carbonyl)-amino]-acetic acid tert-butyl ester

수율 22.0%

용매

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONis introduced
2. 2
   농축then concentrated under reduced pressure
3. 3
   workup.ADDITIONThe reaction mixture is diluted with EtOAc
4. 4
   세척then washed with 1M HCl, sat. NaCl
5. 5
   건조the organic layer is dried (MgSO4)
6. 6
   여과filtered
7. 7
   농축concentrated under reduced pressure to a crude oil that
8. 8
   기타is purified over silica (EtOAc/heptane 1:4)

실험 절차

To a solution of 3-hydroxypicolinic acid (0.20 g, 1.44 mmol) in DMF (5 mL) at 0° C. under N2 is added diisopropylethylamine (DIPEA) (0.75 ml, 4.3 mmol), 1-(3-dimethyl-aminopropyl)-3-ethylcarbodiimide (EDCI) (0.412 g, 2.9 mmol) and 1-hydroxybenzotriazole (HOBt) (0.019 g, 0.14 mmol). The resulting mixture is stirred for 5 min before glycine tert-butyl ester HCl (0.36 g, 2.9 mmol) is introduced. The resulting solution is stirred at room temperature for 3 days then concentrated under reduced pressure. The reaction mixture is diluted with EtOAc then washed with 1M HCl, sat. NaCl, and the organic layer is dried (MgSO4), filtered and concentrated under reduced pressure to a crude oil that is purified over silica (EtOAc/heptane 1:4) to afford 0.078 g (22% yield) of the desired compound as an off-white solid. 1H NMR (400 MHz, CDCl3) δ ppm 11.80 (1H, s), 8.39 (1H, br s), 8.02 (1H, dd, J=4.4, 1.5 Hz), 7.27 (1H, dd, J=8.8, 4.4 Hz), 7.25 (1H, dd, J=8.4, 1.5 Hz), 4.06 (2H, d, J=5.5 Hz), 1.44 (9H, s). HPLC-MS: m/z 197 [M-tBu]+.

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