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[ CAS No. 2483-46-7 ]

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CAS No. :2483-46-7 MDL No. :MFCD00038515
Formula : C16H30N2O6 Boiling Point : 514°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :346.42 g/mol Pubchem ID :7349648
Synonyms :

Safety of [ 2483-46-7 ]

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:

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  • Upstream synthesis route of [ 2483-46-7 ]
  • Downstream synthetic route of [ 2483-46-7 ]

[ 2483-46-7 ] Synthesis Path-Upstream   1~16

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Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 31, p. 12220 - 12228
[2] Journal of Materials Chemistry, 2012, vol. 22, # 19, p. 10035 - 10041
[3] Russian Journal of Bioorganic Chemistry, 2006, vol. 32, # 5, p. 407 - 412
[4] Journal of the American Chemical Society, 2015, vol. 137, # 32, p. 10056 - 10059
[5] Chemical Communications, 2015, vol. 51, # 31, p. 6832 - 6835
[6] Patent: WO2006/121552, 2006, A2, . Location in patent: Page/Page column 28-29; 2/70
[7] Bioconjugate Chemistry, 2010, vol. 21, # 8, p. 1473 - 1478
[8] Macromolecules, 2015, vol. 48, # 6, p. 1688 - 1702
[9] Journal of the American Chemical Society, 2015, vol. 137, # 18, p. 6000 - 6010
[10] Patent: US2015/259535, 2015, A1, . Location in patent: Paragraph 0106
[11] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 2, p. 672 - 676
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Reference: [1] Heterocycles, 1981, vol. 15, # 1, p. 467 - 468
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Reference: [1] Heterocycles, 1981, vol. 15, # 1, p. 467 - 468
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YieldReaction ConditionsOperation in experiment
100% With sodium hydroxide In 1,4-dioxane; water at 20℃; To the solution of Lysine HCl salt in 50 ml 1,4-dioxane/H2O (1:1), 1M NaOH is added until pH reaches 10-11. Then Boc anhydride in dioxane (6.0 g in 20 ml dioxane) is added by an addition funnel. The resulting solution is stirred at room temperature overnight. The mixture is concentrated in vacuo and acidified by 4M KHSO4 until pH=1-2. Extract by Ethyl acetate twice and dried in vacuo. Colorless liquid is obtained and yielding is 100percent
92% With sodium hydroxide In 1,4-dioxane; water at 10 - 20℃; for 20 h; Example 1
Boc-L-Lys(Boc)-OH
A 2 L three-neck flask equipped with a mechanical stirrer was charged with a solution of L-lysine monohydrochloride (50.03 g, 274 mmol) in water (275 ml), 1,4-dioxane (275 ml) and 1 M sodium hydroxide solution (275 mmol, 275 ml) (resulting: pH 10.0).
To this solution was added di-tert-butyl dicarbonate (179 g, 820 mmol) in one portion whilst stirring.
The evolution of gas was noted, and the pH of the reaction mixture slowly decreased.
A Metrohm Titrino 702 SM dosing unit was set up in "Set Endpoint Titration" mode in order to keep the pH of the reaction mixture constant at pH 7.30 by automatically dosing 1 M NaOH. Note:
the reaction mixture apparently formed a buffered system at pH 7.05.
LCMS (NQAD detection) indicated near-complete consumption of the lysine starting material after a reaction time of 20 h.
The reaction mixture was concentrated by rotary evaporation to a total volume of ˜500 mL. Water (250 mL) was added (resulting pH: 8.8) and then EtOAc was added (250 mL).
Solid KHSO4 (˜70 g) was added in portions until a pH of 2.3 was reached (Note: evolution of gas; the mixture formed a buffer at pH 2.3).
The phases were separated, the aqueous layer was extracted with EtOAc (2*250 mL) and the combined organic phases were washed sequentially with 0.25 M KHSO4 (2*100 mL), water (50 mL) and brine (2*50 mL).
Drying over Na2SO4 and concentration in vacuo yielded the title compound as a clear, colorless, sticky mass (98.18 g).
LCMS: Purity (NQAD detection):
99percent, mass in agreement with molecular formula (neg. m/z=345 [M-1]-, 691 [2M-1]-). TLC (EtOAc/heptane=1/1 containing 2 vol percent AcOH, anisaldehyde staining): One major spot (Rf 0.28), no Boc2O present. A small impurity with a higher Rf was visible. Kaiser test: negative (no primary amines present). Isolated yield: 92percent
90% With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 35℃; for 24 h; Lysine hydrochloride (about 5 g, 27.3 mmoi) is dissolved in 50 ml ii2O and to it NaHCO3 (6.9 g, 82,1 mmol) is added and stirred. To this, Dibutyipyrocarbonat (Boc2O) (7.16 g, 65,5 mmoi) in 50 ml Tetrahydrofuran (Ti-IF) is added at a temperature of about 0°C. The solution is stned at room temperature (20°C to 35°C) and atmospheric pressure (1 atm) for aboutl2 hrs. After about 12 his, 7.16g, 65.5 mmoi of Boc2O is added again and stirred for about 12 hrs at room temperature (20°C to 35°C). At the end of the reaction, THF is removed under reduced pressure and the aqueous layer is washed with diethyl ether to remove organic impurities. Then the aqueous layer is acidified to pH 4-5 using citric acid solution. Then the aqueous layer is extracted with Dichloromethane (DCM). The organic layer is then washed with brine, dried over anhydrous Na2SO4. This DCM layer is removed under reduced jressure to obtain BOC-LYS (BOC)-OH with a yield of about 90percent, (‘H NMR: ö 5.6 (d, 1H), 4.9 (s, 1H), 4.15 (t, 1Ff), 3.09 (d, 2H), 1.8 (m, li-I), 1.67 (m, 1H), 1.54-1.32 22F{). [M+Na] obsd. == 369.2137 (calc. == 369.2002)
83% With sodium hydrogencarbonate; sodium hydroxide In ethanol; water at 20℃; for 48 h; Cooling with ice NaOH (0.8 g, 0.02 mol) was dissolved in7.5 mL of water and L-Lysine monohydrochloride (1.83 g, 0.01 mol) was added tothe solution, followed by addition of NaHCO3 (0.42 g, 0.005 mol). Asolution of di-tert-butyl-carbonate(4.55 g, 0.02 mol) in ethanol (10 mL) was added dropwise to the stirringsolution of the amino acid cooled with ice. After one hour, the reactionmixture was warmed up at room temperature and stirred for 2 days. Water (20 mL)was then added to dissolve the precipitate. Unreacted di-tert-butyl-carbonate was extracted three times with petroleumether. The aqueous layer was acidified with NaHSO4 1M up to pH 3 andthe product was extracted with EtOAc. The organic layer was washed twice withwater and dried over NaSO4. The solvent was removed under vacuum,yielding a transparent oil (2860 mg, 83percent yield). 1H NMR (400 MHz,DMSO-d6): δ 12.38 (bs, 1H, COOH), 6.98 (d, J=8.3 Hz, 1H, CH-NH-Boc), 6.74 (t, J=5.6 Hz, 1H, CH2-NH-Boc), 3.82 (m, 1H, CH-NH-Boc),2.88 (m, 2H, CH2-NH-Boc), 1.57 (m, 4H, CH2), 1.31-1.41(m, 20H, t-C4H9, CH2).
29.7 g
Stage #1: With sodium hydroxide In water at 15 - 60℃; for 12 h;
Stage #2: With hydrogenchloride In water at 10 - 15℃;
Examplel Preparation of 2,6-bis-tertiarvbutoxycarbonylamino hexanoic acidTo a solution of L-lysine monohydrochloride (25g, 0.14mol) and sodium hydroxide (15g) in water (250 ml), ditertiary butyl dicarbonate (70.0 g, 0.32 mol) was added at 15-25°C. The temperature was slowly raised to 55-60 °C and the reaction mixture was stirred for 12 hours.. After completion of reaction, ( monitored by TLC), the reaction mixture was cooled to 10-15°C and pH was adjusted to 2.5-3.5 with 2N hydrochloric acid. The reaction mass' was then extracted with dichloromethane (2 x 125 ml) and combined organic layer was successively washed with water (150 ml) and brine (150 ml). Dichloromethane layer was distilled under vacuum at 30-40 °C to obtain 29.7g of title compound as a viscous oily mass having purity 96.5percent by HPLC.

Reference: [1] Patent: US2014/127138, 2014, A1, . Location in patent: Paragraph 0321; 0322
[2] Patent: US2016/376618, 2016, A1, . Location in patent: Paragraph 0206-0212
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 4, p. 1428 - 1436
[4] Patent: WO2014/97178, 2014, A1, . Location in patent: Page/Page column 49
[5] New Journal of Chemistry, 2018, vol. 42, # 5, p. 3192 - 3195
[6] Russian Journal of Applied Chemistry, 2005, vol. 78, # 6, p. 1003 - 1007
[7] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 21, p. 6891 - 6899
[8] Patent: WO2013/11526, 2013, A1, . Location in patent: Page/Page column 15-16
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YieldReaction ConditionsOperation in experiment
92% With sodium hydroxide In 1,4-dioxane; water at 20℃; for 12 h; To a solution of l-lysine monohydrate (5.09 g, 31.0 mmol) in water/dioxane (1:1, 100 mL) were added di-tert-butyl dicarbonate (16.9 g, 78.0 mmol) and 1 N NaOH aq (35 mL).
The reaction mixture was stirred at room temperature 12 h and then concentrated in vacuo until approximately 50 mL remained.
The pH was adjusted to 1-2 by careful addition of an aqueous KHSO4 solution (150 g/L).
The suspension was extracted three times with ethyl acetate.
The combined organic layers were dried over MgSO4 and the solvent was removed under reduced pressure to afford the product (9.89 g, 28.5 mmol, 92percent) as an oil. 1H NMR (DMSO-d6, 200.1 MHz): δ = 12.40 (s, 1H, OH), 6.98 (d, J = 7.9 Hz, 1H), 6.76 (t, J = 5.4 Hz, 1H), 3.75-3.86 (m, 1H), 2.50-2.83 (m, 2H), 1.37 (s, 18H), 1.14-1.68 (m, 6H) ppm; 13C NMR (DMSO-d6, 50.3 MHz): δ = 173, 155.1, 77.4, 76.8, 52.9, 29.9, 28.6, 27.7, 22.4 ppm (one signal, probably around 40 ppm, is hidden by the solvent signal).
92% With sodium hydroxide In 1,4-dioxane; water at 20℃; for 12 h; To a solution of L-lysine monohydrate (5.09 g, 31.0 mmol) in water/dioxane (1:1, 100 mL) were added di-tert-butyl dicarbonate (16.9 g, 78.0 mmol) and 1 N NaOH aq. (35 mL). The reaction mixture was stirred at room temperature 12 h and then concentrated in vacuo until approximately 50 mL remained. The pH was adjusted to 1–2 by careful addition of an aqueous KHSO4 solution (150 g/L). The suspension was extracted three times with ethyl acetate. The combined organic layers were dried over MgSO4 and the solvent was removed under reduced pressure to afford the product (9.89 g, 28.5 mmol, 92percent) as an oil. 1H NMR (DMSO-d6, 200.1 MHz): δ = 12.40 (s, 1H, OH), 6.98 (d, J = 7.9 Hz, 1H), 6.76 (t, J = 5.4 Hz, 1H), 3.75–3.86 (m, 1H), 2.50–2.83 (m, 2H), 1.37 (s, 18H), 1.14–1.68 (m, 6H) ppm; 13C NMR (DMSO-d6, 50.3 MHz): δ = 173, 155.1, 77.4, 76.8, 52.9, 29.9, 28.6, 27.7, 22.4 ppm (one signal, probably around 40 ppm, is hidden by the solvent signal).
90%
Stage #1: With sodium carbonate In tetrahydrofuran; water for 0.25 h;
Stage #2: at 0℃;
Stage #3: With hydrogenchloride In tetrahydrofuran; water; ethyl acetate
Example 1; Synthesis of Lysine^-aminoethyl ester trihydrochloride ("trihydrochloride salt ") Di-Boc lysine (ref. 22117-48); L-lysine (450 grams, 2.46 mol) was charged to a 12 liter flask followed by water (3.6 liters) and THF (3.6 liters). Sodium carbonate (540 grams, 5.1 mol) was added and the mixture was stirred for 15 minutes. The mixture was then cooled to 0°C in an ice bath and to it was added di-/ert-butyl-dicarbonate (1 102 grams, 5.05 mol) in portions. The mixture was allowed to stir overnight. Ethyl acetate (1.5 liters) was added to the reaction mixture followed by 6N HC1 until the pH was <3 (caution: gas evolution.) The layers were allowed to separate and the aqueous layer was removed. The organic layer was dried over magnesium sulfate, then was concentrated under reduced pressure to give an oil. Mass recovery was approximately 770 grams (90percent yield).
90% With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; Commercially available L-lysine (0.146 g, 1.0 mmol) dissolved in H2O (5.0 mL) was mixed with NaHCO3 (0.252 g, 3.0 mmol). B0C2O (1 .048 g, 4.8 mmol) in 10.0 mL of THF was subsequently added to the mixture at 0 °C and stirred at room temperature overnight. At the end, THF was evaporated and the mixture was washed with diethyl ether. The aqueous layer was acidified to pH = 6 with citric acid, followed by CH2CI2 extraction. The organic layer was washed with water and brine, and dried over anhydrous Na2SO4. The mixture was then concentrated and purified by flash column chromatography (eluted with CH2Cl2/MeOH from 100:0 to 15:1 , v/v) to afford the desired compound as white solid (Yield: 90 percent).
64.3% With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 24 h; General procedure: l-lysine, l-alanine, l-leucine, l-isoleucine, l-phenylalanine, l-threonine (5g, 1 equiv) was dissolved in H2O (100mL), and to it NaOH (3 equiv) was added and stirred. To this, di-tert-butyl dicarbonate (Boc2O) (2.4 equiv) in 50mL of tetrahydrofuran (THF) was added at 0°C [39]. Then the reaction mixture was stirred at room temperature for 24h. At the end of the reaction, THF was removed under reduced pressure and the aqueous layer was washed with diethyl ether to remove organic impurities. Then the aqueous layer was acidified to pH 4–5 using 1M H2SO4 aqueous solution. The aqueous layer was then extracted with dichloromethane (DCM). The organic layer was then washed with brine and dried over anhydrous Na2SO4. The organic layer was removed under reduced pressure to obtain the compound.
64.3% With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 24 h; l-lysine (5g, 1 equiv.) was dissolved in H2O (100mL), and NaOH (3 equiv) was added to this solution and stirred. Di-tert-butyl dicarbonate (Boc2O) (2.4 equiv) in 50mL of tetrahydrofuran (THF) was added at 0°C [53]. Then the reaction mixture was stirred at room temperature for 24h. At the end of the reaction, THF was removed under reduced pressure and the aqueous layer was washed with diethyl ether to remove organic impurities. Then the aqueous layer was acidified to pH 4–5 using 1MH2SO4 aqueous solution. The aqueous layer was then extracted with dichloromethane (DCM). The organic layer was then washed with brine and dried over anhydrous Na2SO4. The organic layer was removed under reduced pressure to obtain the compound.
63% With sodium hydroxide In tetrahydrofuran; water at 20℃; for 24 h; Cooling with ice Took L- lysine (5g, 34.2mmol) and sodium hydroxide (4.1g, 102.61mmol) was added in 250mL single-port flask, 100mL of water was added, under ice-cooling with stirring, to a light brown clear yellow system; di-tert butyl ester (Boc2O) (17.92g, 82.09mmol) was dissolved in 50mL of tetrahydrofuran was then added dropwise (1d / s) to the reaction system; After the addition was complete, the system was transferred into a reaction was continued at room temperature for 24 hours.The reaction time after the reaction is stopped, the system was removed by rotary evaporation under reduced pressure of tetrahydrofuran, and the system is washed with ether (50ml × 2) removing the organic impurities in the system; then with 1M sulfuric acid solution to adjust the system pH 4 and then extracted with dichloromethane (50mL × 3) and the combined organic phase was washed with saturated sodium chloride (50mL × 1), and finally dried over anhydrous sodium sulfate, suction filtered, concentrated, and dried in vacuo to give a yellow foamy solid 7.5g, 63percent yield.
45% With potassium hydroxide In water at 50℃; Similar to the method of Ke et al. (42), L-lysine (4.4 g, 30mmol) and KOH (2.3 g, 39 mmol) were dissolved in water (100ml) and THF (12.5 ml). Di-tert-butyl dicarbonate (14.4 g, 66 mmol) was added in portions, and the mixture was stirred for14 h at 50 °C. A 1 M solution of HCl was added dropwise to adjust the pH to 5.5, followed by extraction with EtOAc (3 100 ml). The combined extracts were dried with MgSO4 and concentrated in vacuo. Column chromatography on silica gel with hexane/EtOAc (2:1) yielded N,N-di-(tert-butyloxycarbonyl)-L-lysine (4.6 g, 13.3 mmol, 45percent) as a colorless solid.
34.2 g
Stage #1: With sodium carbonate In tetrahydrofuran; water for 0.25 h;
Stage #2: at 0 - 20℃;
To a solution of L-lysine (20 g, 109.5 mmol) in 160 mL of water and 160 mL of tetrahydrofuran was added sodium carbonate (24 g, 226.4 mmol). After stirring for 15 minute, the reaction mixture was cooled down to 0 °C and di-tert-butyl-dicarbonate (48.93 g, 224.4 mmol) was slowly added. After stirring overnight at room temperature, the reaction mixture was diluted with ethyl acetate (66.7 mL) and 6N hydrochloric acid solution (56.7mL) was added to adjust pH to 3 or lower. The aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate and concentrated under reduced pressure to provide the desired product (34.2 g, 98.8 mmol).

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[4] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 6, p. 1241 - 1250
[5] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 20, p. 4606 - 4609
[6] Patent: WO2012/106588, 2012, A2, . Location in patent: Page/Page column 17-18
[7] Journal of Medicinal Chemistry, 2017, vol. 60, # 9, p. 3684 - 3702
[8] Patent: WO2018/187867, 2018, A1, . Location in patent: Page/Page column 24
[9] Helvetica Chimica Acta, 2000, vol. 83, # 2, p. 322 - 327
[10] Organic and Biomolecular Chemistry, 2013, vol. 11, # 21, p. 3461 - 3468
[11] Journal of the American Chemical Society, 2000, vol. 122, # 33, p. 7927 - 7935
[12] Tetrahedron, 2003, vol. 59, # 31, p. 5837 - 5848
[13] Angewandte Chemie - International Edition, 2014, vol. 53, # 4, p. 1113 - 1117[14] Angew. Chem., 2013, vol. 126, # 04, p. 1131 - 1135,5
[15] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 1489 - 1509
[16] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 925 - 945
[17] Patent: CN105566149, 2016, A, . Location in patent: Paragraph 0043; 0044; 0045
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[19] Journal of Biological Chemistry, 2013, vol. 288, # 34, p. 24717 - 24730
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YieldReaction ConditionsOperation in experiment
93% With triethylamine In 1,4-dioxane; water for 18 h; Cooling with ice [0043] Nα-(tert-butoxycarbonyl)-L-lysine (1) (985 mg, 4 mmol) was dissolved in anhydrous 1,4-dioxane (3 mL) and water (3 mL). After adding triethylamine (615 μL, 4.4 mmol), to the solution was added di-tert-butyl dicarbonate (960 mg, 4.4 mmol) dropwise under ice-cooling, and then the mixture was stirred for 18 hours. Completion of the reaction was confirmed by TLC (ethyl acetate:n-hexane=5:1), and the reaction solution was poured into a 0.5 N aqueous solution of hydrochloric acid (80 mL). The mixture was extracted with ethyl acetate (3×40 mL) and the organic layer was washed with saturated saline (80 mL) and dried over anhydrous magnesium sulfate. After evaporation under a reduced pressure, the obtained material was purified by flash column chromatography (ethyl acetate:n-hexane=1:1 to 2:1) to give intermediate 2 (1.29 g, 93percent) as a white solid. [0044] 1H-NMR (300 MHz, CDCl3) δ: 5.21 (br s, 1H), 4.62 (br s, 1H), 4.28 (br s, 1H), 3.14 (d, 2H, J=6.0 Hz), 1.88 (br s, 1H), 1.76 (br s, 1H), 1.45-1.23 (m, 22H), 0.92-0.88 (m, 1H).
Reference: [1] Patent: US2015/80551, 2015, A1, . Location in patent: Paragraph 0043; 0044
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[2] European Journal of Medicinal Chemistry, 2011, vol. 46, # 11, p. 5387 - 5397
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Reference: [1] Patent: WO2006/121552, 2006, A2, . Location in patent: Page/Page column 28-29; 2/70
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Reference: [1] Journal of the American Chemical Society, 1965, vol. 87, p. 611 - 619
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Reference: [1] Gazzetta Chimica Italiana, 1964, vol. 94, p. 853 - 865
[2] Helvetica Chimica Acta, 1963, vol. 46, p. 1637 - 1669
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Reference: [1] Hoppe-Seyler's Zeitschrift fuer physiologische Chemie, 1969, vol. 350, # 12, p. 1556 - 1562
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Reference: [1] Journal of Molecular Catalysis A: Chemical, 2016, vol. 424, p. 297 - 303
  • 14
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Reference: [1] Gazzetta Chimica Italiana, 1964, vol. 94, p. 743 - 759
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Reference: [1] Gazzetta Chimica Italiana, 1964, vol. 94, p. 743 - 759
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Reference: [1] Gazzetta Chimica Italiana, 1964, vol. 94, p. 743 - 759
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