Sodium Bicarbonate → 3-[(5-Carboxy-furan-2-ylmethyl)-amino]-phthalic acid dimethyl ester

반응식

[CH:1]([C:3]1[O:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1)=O.[CH3:11][O:12][C:13](=[O:30])[C:14]1[C:15](=[C:20]([NH:24]CCCCC)[CH:21]=[CH:22][CH:23]=1)[C:16]([O:18][CH3:19])=[O:17].C([O-])(O)=O.[Na+]>>[CH3:11][O:12][C:13](=[O:30])[C:14]1[C:15](=[C:20]([NH:24][CH2:1][C:3]2[O:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=2)[CH:21]=[CH:22][CH:23]=1)[C:16]([O:18][CH3:19])=[O:17]

참가 물질

반응물 3

HCID 516892Sodium Bicarbonate

HCID 27937195-Formyl-2-furancarboxylic Acid

HCID 210401313-Pentylamino-phthalic acid dimethyl ester

생성물 1

HCID 210401283-[(5-Carboxy-furan-2-ylmethyl)-amino]-phthalic acid dimethyl ester

실험 절차

5-Formyl-furan-2-carboxylic acid (1 g, 7.14 mmol) was treated in the same manner as described above for the synthesis of 3-pentylamino-phthalic acid dimethyl ester except the combined aqueous NaHCO3 extracts were washed with methylene chloride (1×70 ml) and the pH adjusted to 2–3 by dropwise addition of concentrated HCl. The mixture was then extracted with ethyl acetate (3×75 ml). The combined ethyl acetate extracts were washed with brine (1×100 ml), dried (magnesium sulfate), and filtered. The solvent was evaporated in vacuo to give 0.90 g product as an off-white solid: 1H NMR (CDCl3) δ 7.42–7.36 (m, 1H), 7.16 (d, J=3.5 Hz, 1H), 7.03–6.97 (m, 2H), 6.90 (dd, J=1.0 Hz and 7.3 Hz, 1H), 6.48 (d, J=3.5 Hz, 1H), 4.60 (d, J=5.2 Hz, 2H), 3.82 (s, 3H), 3.81 (s, 3H).