11-(METHACRYLOYLAMINO)UNDECANOIC ACID synthesis

Yield:59178-93-7 92%

Reaction Conditions:

with sodium carbonate in tetrahydrofuran;water at 0; for 5 h;

Steps:

1

Example 1; [0049] Synthesis of 11 -Methacrylamidoundecanoic Acid; 10-Aminodecanoic acid (4.04 g, 20 mmol) was dissolved in 300 ml of THF and water (1 :1 ) in an ice-water bath, and then sodium carbonate (3.18 g, 30 mmol) was added. Methacryloyl chloride (3.15 g, 30 mmol) was slowly added, and the mixture was stirred for 5 h. After reaction was complete, the solution was neutralized to pH 5 with HCI. Then the solvent was removed by evaporation, and the residue was extracted with 200 ml CH₂CI₂, producing a white solid. Recrystallization from a hexane/ethyl acetate solution gave 4.96 g product (yield 92%). Alternatively, replacing THF/H₂O with CHCI₃ gave a similar or higher yield.Analysis: ¹HNMR (CDCI₃, 400 MHz) δ: 5.69 (s, 1 H, CHH=), 5.32 (s, 1 H, CHH=), 3.30 (m, 2H, NHCH₂CH₂), 2.34 (t, 2H, J = 7.4 Hz, CH₂CH₂COOH), 1.97 (s, 3H, CH₂=CHCH₃), 1.48-1.70 (m, 4H, NHCH₂CH₂CH₂ and CH₂CH₂CH₂COOH), 1.24-1.38 (m, 12H, NHCH₂CH₂(CH₂)₆CH₂CH₂COOH). ¹³C-NMR (CDCI₃, 400 MHz) δ: 179.50 (COOH), 168.86 (CH₂=CCH₃CONHCH₂), 140.26 (CH₂=CCH₃CONHCH₂), 119.67 (CH₂=CCH₃), 40.00 (CH₂=CCH₃CONHCH₂CH₂), 34.29 (CH₂CH₂COOH), 29.70, 29.57, 29.47, 29.40, 29.35, 29.19, 27.10, 24.90(CH₂=CCH₃CONHCH₂(CH₂)₈CH₂COOH), 18.92 (CH₂=CCH₃). ESMS (THF/H₂O, negative ion): m/z = 268.2 ([M-H]^", calculated: 268.2).

References:

WO2008/100907,2008,A2 Location in patent:Page/Page column 26-27