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CAS No. : | 60-32-2 | MDL No. : | MFCD00008238 |
Formula : | C6H13NO2 | Boiling Point : | - |
Linear Structure Formula : | H2N(CH2)5COOH | InChI Key : | SLXKOJJOQWFEFD-UHFFFAOYSA-N |
M.W : | 131.17 | Pubchem ID : | 564 |
Synonyms : |
EACA;Epsilon-Amino-n-caproic Acid;Hepin;Capracid;Aminocaproic acid;NSC 400230;NSC 212532;NSC 26154;ε-Aminocaproic Acid;(6-)ε-?Aminocaproic acid;6-Aminohexanoic acid
|
Chemical Name : | 6-Aminocaproic Acid |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 420℃; for 4h; | DIEA (78 pL, 0.50 mmol) and 6-aminohexanoic acid (44 mg, 0.33 mmol) were added to a solution of succinimidyl-4-(N-maleimidomethyl)cyclohexane-1 -carboxylate (0.30 mmol) in DMF (5 mL) in a 40 mL vial, and the reaction mixture was stirred at rt for 4 h. Thereaction mixture was then purified by HPLC and lyophilized to give 76-(4-((2,5-dioxo-2,5- dihydro-1 H-pyrrol-1 -yl)methyl)cyclohexanecarboxam ido)hexanoic acid (i-2). MS (M+1) =351, 1H-NMR (MeOD, 400 MHz) O 7.79 (bs, 1H), 6.76 (s, 2H), 3.29 (d, 2H, J=4.4 Hz), 3.10 (m, 2H), 2.24 (t, 2H, J=7.2 Hz), 2.07 (m, 4H), 1.56(m, 3H) 1.43 (m, 3H), 1.33 (m, 3H), 0.97 (m, 2 H). | |
In water; N,N-dimethyl-formamide; at 20℃; for 4.08333h; | A solution of succinimidyl 4-[N-maleimidomethyl]cyclohexane-l-carboxylate (PIERCE Ref: 22360) (25 mmol) in DMF (10OmL) was stirred for 5 min, and was added at room temperature to a solution of 6-aminohexanoic acid (50 mmol) (SIGMA Ref: A2504) in H2O(50 mL). The mixture was stirred for 4h at room temperature. Dichloromethane was added(100 mL) and the organic layer was washed with water (3x150 mL) and then with 5percent aqueous citric acid (3x150 mL) to remove 6-aminohexanoic acid excess. The organic layer was dried under vacuum and the resulting white powder was stored at -200C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In N,N-dimethyl-formamide; at 20℃; | biotin-NHS (1 eq., 388 mg, 1.14 mmol) was dissolved in the anhydrous DMF (8.54 mL). To the resulting solution was added 6-aminocaproic acid (1 eq., 149 mg, 1.14 mmol) andthe mixture was stirred at r.t. overnight and then concentrated to yield 1:1 mixture of the product and NHS. To the product was then added 95:1 :4 mixture of EtOH-AcOH-H20. The resulting suspension was heated to boiling, filtered, and left to crystallize to yield compound 9 (305 mg, 0.854 mmol, 75 percent) as a white fluffy solid. The structure of 9 was confirmed by ESI-MS analysis (Method 1).ESI-MS m/z: 358.3 [M+H] |
1.455 g | With sodium hydrogencarbonate; In water; N,N-dimethyl-formamide; at 20℃; for 16h; | epsilon-Aminocaproic acid (966mg, 8.4mmol) was dissolved in 30mL 1M aqueous NaHCO3 solution. Then N-hydroxysuccinimidobiotin (3.09g) in 35mL DMF was added dropwise to the solution and the mixture was stirred at room temperature for 16h. The solution was concentrated under reduced pressure to remove partial solvent and 150mL aqueous citric acid (100g/L) was then added and stirred at 60°C for 30min. The precipitate was collected by filtration and washed with distilled water. The precipitate was dissolved in a mixture of isopropanol and water (8:2, v/v) and kept at 4°C to give pure 3 (1.455g, 50percent) as a yellowish crystal; IR cm?1 (KBr): 3200?3500, 3070, 2932, 2859, 1696, 1644, 1543, 1475, 1391, 1324, 1265, 1118; 1H NMR (600MHz, DMSO-d6): delta 7.75 (1H, t, J=5.4Hz, C6?NH), 6.45 (1H, s, C13?NH), 6.38 (1H, s, C14?NH), 4.35?4.27 (1H, m, H-14), 4.12 (1H, m, H-13), 3.09 (1H, m, H-12), 3.00 (1H, m, H-6) 2.82 (1H, dd, J=12.4, 5.1Hz, H-15a), 2.57 (1H, d, J=12.4Hz, H-15b), 2.19 (2H, t, J=7.4Hz, H-2), 2.04 (2H, t, J=7.3Hz, H-8), 1.20?1.67 (14H, m). 13C NMR (150MHz, DMSO-d6): delta 171.84 (C-1, C-7), 162.74 (C-16), 61.06 (C-13), 59.20 (C-14), 55.44 (C-12), 39.68 (C-15), 38.25 (C-6), 35.21 (C-8), 29.05 (C-2), 28.92, 28.21, 28.04, 26.04, 25.73, 25.36. |
368.3 mg | With sodium hydrogencarbonate; In water; acetone; at 20℃; for 12h; | General procedure: Biotin-NHS was ammonolyzed withlinkers to afford biotin-linker products [Biotin-AAn-COOH (n = 1, 3, 5, and 7) orBiotin-PEG(n+1)-COOH (n = 1, 2 and 3)]. The linker [AAn (n = 1, 3, 5, and 7) orNH2-PEG(n+1)-COOH (n = 1, 2 and 3), 1 eq.] was dissolved in 4 mL water solutionrespectively, and 240.0 mg NaHCO3 was added to the solution. The reaction mixturewas stirred and the Biotin-NHS (1 eq.) and acetone (500 ul) were added subsequently.After stirring for 12h at room temperature, the solvent was removed by vacuum, andthe crude was dispersed in water, adjusting the pH by 2M HCl to pH=3. The mixturesolution was filtered, washed by water and concentrated under reduced pressure toachieved Biotin-linker products [Biotin-AAn-COOH (n = 1, 3, 5, and 7) orBiotin-PEG(n+1)-COOH (n = 1, 2 and 3)]2, 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1-methyl-pyrrolidin-2-one; at 50 - 100℃; | 7.5 kg of biotin (III), triethylamine (15 l, 2 V, 3.5 eq), NMP (15 l, 2 V) and, finally, chloroacetonitrile (3.5 kg, 0.47 OU, 1.5 eq) are charged to a reactor. The medium is heated to 60° C. After this temperature has been maintained for 2 h, an LC analysis shows that all the biotin has been converted into compound (III') (<2percent). The medium is cooled to 50° C. and then transferred into another reactor, containing aminocaproic acid (9.05 kg, 1.206 OU, 2.2 eq). Rinsing is carried out with NMP (0.1 V). The medium is heated to 100° C. and maintained at this temperature for 2 h. An LC analysis shows that less than 2percent of activated biotin (III') remains. The medium is cooled to 60° C. Acetonitrile (60 l, 8 V) preheated to 55° C. is run in. The mixture is stirred for 30 minutes at 60° C., and then cooled to 20° C. Stirring is carried out for 1 h. The suspension is filtered, then rinsing is carried out with 3 times acetonitrile (5 V) and then with THF (5 V). Drying is carried out under vacuum at a maximum of 60° C. until there is no change in weight. 12.0 kg of the compound (II) are thus obtained, with a yield of 109percent and an organic purity, measured by LC, of 98.6percent.10.0 kg of the compound (II) are recharged to a reactor. Hydrochloric acid (90 l, 9 V of water+10 l, 1 V of 36percent HCl) is then added. The suspension is stirred at 20° C. for 30 min. The suspension is filtered and rinsing is carried out 3 times with water (4 V, 40 l), then twice with THF (3.5 V). Drying is carried out under vacuum at a maximum of 45° C. until there is no change in weight. 6.1 kg of the compound (II) are thus obtained, with a yield of 66percent. |