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CAS No. : | 111-16-0 | MDL No. : | MFCD00004425 |
Formula : | C7H12O4 | Boiling Point : | No data available |
Linear Structure Formula : | (CH2)5(COOH)2 | InChI Key : | WLJVNTCWHIRURA-UHFFFAOYSA-N |
M.W : | 160.17 | Pubchem ID : | 385 |
Synonyms : |
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Chemical Name : | Heptanedioic acid |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With hydrogenchloride; In methanol; ethyl acetate; | A. Methyl hydrogen pimelate (7) A mixture of pimelic acid (15) (75.1 g, 0.47 mol), dimethyl pimelate (50.1 g, 0.27 mol), hydrochloric acid (8 mL, 0.1 mol), methanol (25 mL, 0.62 mol) and di-n-butyl ether (20 mL) was heated (oil bath: 100-110 C.) under N2 overnight. After cooling to room temperature, EtOAc (200 mL) was added and the mixture was washed with water (2*100 mL), saturated NaCl (2*100 mL) and dried (Na2 SO4). The crude oil was fractionally distilled (vigreux, 125-130 C., 0.7 mm Hg) to provide a clear oil (55.5 g, 68%, purity?95%. Based on NMR analysis, the clear oil was determined to be methyl hydrogen pimelate (7) (1 H NMR)): TLC (SiO2, MeOH/EtOAc/hexane (2:8:15, v/v)) Rf =0.25-0.34; 1 H NMR (300 MHz, CDCl3) δ3.67 (s, 3 H), 2.40-2.28 (m, 4 H), 1.72-1.58 (m, 4 H), 1.45-1.32 (m, 2 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20℃; for 18.0h; | [00350] Heptanedioic acid (1.6 g, 9.99 mmol) was dissolved in tetrahydrofuran (THF) (100 mL), and l-hydroxypyrrolidine-2,5-dione (2.299 g, 19.98 mmol) was then added, followed by the addition of DCC (4.12 g, 19.98 mmol). The mixture was stirred at room temperature for 18 hours until HPLC analysis indicated the completion of the reaction. The solid was removed by filtration through a celite pad, and washed with THF (3 x 2 mL). The combined filtrate was concentrated and purified by flash chromatography to yield bis(2,5-dioxopyrrolidin-l-yl) heptanedioate (ER-001236140) as a white solid (2.5 g, 71% yield). 1HNMR (400 MHz) δ ppm 2.83 (s, 8H), 2.64 (t, J = 7.6 Hz, 4H), 1.80 (dt, J= 7.6 Hz, 4H), 1.59-1.51 (m, 2H). LCMS (M+H)=355.2. |