Trans-4-(Maleimidomethyl)cyclohexanecarboxylic Acid synthesis
- Product Name:Trans-4-(Maleimidomethyl)cyclohexanecarboxylic Acid
- CAS Number:69907-67-1
- Molecular formula:C12H15NO4
- Molecular Weight:237.25
![Cyclohexanecarboxylic acid, 4-[[(3-carboxy-1-oxo-2-propen-1-yl)amino]methyl]-, trans-](/CAS/20200515/GIF/953817-12-4.gif)
953817-12-4
69907-67-1
Step B: Maleamic acid (36.8 g, 144 mmol) and sodium acetate (13.6 g, 165 mmol) prepared in Step A were dissolved in acetic anhydride (368 mL), and the mixture was transferred to a sealed glass reaction vessel and heated to react for 3 hours at 120 °C. Upon completion of the reaction, the cooled black slurry reaction mixture was slowly poured into water (3 L), stirred thoroughly and extracted with dichloromethane. The organic layers were combined, dried with anhydrous sodium sulfate, filtered through a sintered glass funnel, and the filtrate was evaporated to dryness and dried under high vacuum to afford the target product trans-4-(maleimidomethyl)cyclohexanecarboxylic acid as a yellow solid (7.00 g, 20% yield). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 6.73 (s, 2H), 3.40 (d, 2H, J = 7 Hz), 2.28 (m, 1H), 2.06 (m, 2H), 1.75 (m, 3H), 1.42 (m, 2H), 1.03 (m, 2H).
953817-12-4
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69907-67-1
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Yield:69907-67-1 7 g
Reaction Conditions:
with sodium acetate;acetic anhydride at 120; for 3 h;Sealed tube;
Steps:
1.B
Step B: The maleamic acid from Step A (36.8 g, 144 mmol) and sodium acetate (13.6 g, 165 mmol) were dissolved in acetic anhydride (368 mL), sealed in a glass reaction vessel, and heated to 120°C for 3 hours. The cooled reaction mixture (a black syrup) was poured onto water (3 L), stirred, and extracted with dichloromethane. The organic layer was dried over Na2504, filtered over a sintered glass funnel, and the clear filtrate evaporated and dried under high vacuum giving the title compound as a yellow solid (7.00 g, 20%). 1H NMR (300 MHz, CDC13) 3 6.73 (s, 2H), 3.40 (d, 2H, J = 7 Hz), 2.28 (m, 1H), 2.06 (m, 2H), 1.75 (m, 3H), 1.42 (m, 2H), 1.03 (m, 2H).
References:
WO2015/31396,2015,A1 Location in patent:Paragraph 00103
108-31-6
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1197-18-8
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69907-67-1
86 suppliers
$29.00/250mg
69907-68-2
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69907-67-1
86 suppliers
$29.00/250mg
1197-18-8
901 suppliers
$10.00/5g
69907-67-1
86 suppliers
$29.00/250mg