Trifluoroacetic acid → (3,5-Dihydroxypicolinoyl)glycine

HRID 1024526노트

반응식

HRID 1024526 반응식
C([O:5][C:6](=[O:19])[CH2:7][NH:8][C:9]([C:11]1[C:16]([OH:17])=[CH:15][C:14]([OH:18])=[CH:13][N:12]=1)=[O:10])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[OH:17][C:16]1[C:11]([C:9]([NH:8][CH2:7][C:6]([OH:19])=[O:5])=[O:10])=[N:12][CH:13]=[C:14]([OH:18])[CH:15]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 59513079[(3,5-Dihydroxy-pyridine-2-carbonyl)-amino]-acetic acid tert-butyl ester

생성물 1

HCID 24891198(3,5-Dihydroxypicolinoyl)glycine수율 89%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of [(3,5-dihydroxy-pyridine-2-carbonyl)-amino]-acetic acid tert-butyl ester, 28, (0.10 g, 0.37 mmol) in CH2Cl2 (4 mL) at room temperature is added trifluoroacetic acid (1 mL). The reaction is stirred for 16 hours at room temperature and then concentrated under reduced pressure. The solid that remains is collected by filtration, washed with Et2O to afford 0.070 g (89% yield) of the desired compound as a colorless solid. 1H NMR (250 MHz, DMSO-d6) δ ppm 10.86 (1H, br s), 9.00 (1H, t, J=6.1 Hz), 7.77 (1H, d, J=2.4 Hz), 6.69 (1H, d, J=2.4 Hz), 3.95 (1H, d, J=6.2 Hz). HPLC-MS: m/z 213 [M+H]+.

후처리

  1. concentrationconcentrated under reduced pressure
  2. filtrationThe solid that remains is collected by filtration
  3. washwashed with Et2O

출처 및 근거

ORD 기록
ord-4365370dc3984b159d00aa9e6f2c5f06
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722895B2

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