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Structure of 7377-03-9 * Storage: {[proInfo.prStorage]}
* 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.
With hydroxylamine hydrochloride; potassium hydroxide In ethanol; water at 5 - 55℃; for 3 h;
To the 1000 mL four-necked flask was added hydroxylamine hydrochloride(48.7 g, 0.70 mol, 1.4 eq), water (50 g),Ethanol (200 g, 2.3X), stirred at room temperature until hydroxylamine hydrochloride was dissolved,Then joinEthyl octanoate(86.7 g, 0.5 mol, 1.0 eq), Stirred at room temperature to form a two-phase system, and then cooled to 5 ~ 10 ,Slowly add 40percent KOH (168 g, 1.2 mol, 2.4 eq), Dripping finished, and then heated to 50 ~ 55 , insulation reaction 3 h,GC in the control of n-octanoic acid ethyl ester raw materials disappeared, stop the reaction,Cooled to 5-10 ° C, concentrated hydrochloric acid (90 mL) was added slowly,Adjust the pH = 6.4 ~ 6.7, precipitate a large number of white solid, filter,Dried at 50 for 8 h, the crude product was recrystallized from benzene,A white flocculent solid was 78.8 g, yield 91.1percent
Reference：
[1] Patent: CN106966925, 2017, A, . Location in patent: Paragraph 0022; 0023
[2] Nippon Nogei Kagaku Kaishi, 1940, vol. 16, p. 504[3] Bl.agric.chem.Soc., 1940, vol. 16, p. 100[4] Chem.Abstr., 1941, p. 730
[5] Journal of the American Chemical Society, 1989, vol. 111, # 1, p. 114 - 120
[6] International Journal of Chemical Kinetics, 2016, vol. 48, # 10, p. 601 - 608
[7] Journal of Molecular Liquids, 2016, vol. 221, p. 805 - 814
2
[ 111-11-5 ]
[ 7377-03-9 ]
Yield
Reaction Conditions
Operation in experiment
94.7%
With hydroxylamine hydrochloride; sodium hydroxide In methanol; water at 5 - 40℃; for 5 h; Large scale
To the 500 L enamel reactor was added hydroxylamine hydrochloride (45.1 kg, 1.3 eq),Water (21 kg), methanol (84 kg, 1.06X),Stir at room temperature to hydroxylamine hydrochloride, and then add methyl octanoate(79.1 kg, 1.0 eq) and stirred at room temperature to form a two-phase system, Then cooled to 5 to 10 ° C, and 30percent NaOH was slowly added (167 kg, 2.5 eq), the drop was completed, and then heated to 35 ~ 40 ,Incubation reaction 5 h, GC in the control of n-octanoic acid methyl ester raw material disappeared,Stop the reaction, cooling to 0 ~ 5 , slowly adding concentrated hydrochloric acid (110 kg),Adjust the pH = 6.4 ~ 6.7, precipitate a large number of white solid, filter,Dried at 50 for 8 h, the crude product was recrystallized from methanol,White flocculent solid 75.4 kg, yield 94.7percent
85%
With hydroxylamine hydrochloride; triethylamine In water at 0 - 50℃; for 14.5 h;
At 0 to 10 ° C, 116.4 g of triethylamine (1.15 mol) Was added dropwise to a solution containing 76.5 g of hydroxylamine hydrochloride (1. 1 mol) And 500 mL of water in a reaction flask, After all the addition of triethylamine, Continue to react for 30 minutes, 158.2 g of methyl octanoate (1.0 mol) was added dropwise to the reaction flask over 30 minutes and then heated to 50 ° C for 14 hours. After the completion of the reaction, the reaction was allowed to proceed to room temperature, and the filter cake was dried to give 135.3 g of octanoic acid. The yield was 85percent, NMR (DMS0-d6, 400 MHz): δ 10.33 (br, 1 H), 8.64 (br, (T, 2H), 1.54-1.41 (m, 2H), 1.34-1.15 (m, 8H), 0.86 (t, 3H). 46 g of sodium hydroxide (1.15 mil) was added portionwise to the above filtrate at 0 to 10 ° (y, yielding 107.5 g of triethylamine oil).
83%
With hydroxylamine hydrochloride; calcium oxide In methanol at 10 - 50℃; for 2.5 h; Autoclave
Under low temperature stirring, 33.6 g quick lime (0.6 mol) was added in portions to a vial containing 41.7 g hydroxylamine hydrochloride (0.6 mol) And 200mL of methanol reaction flask, Keep the internal temperature does not exceed 10 , Lime to be added after all, Continue for 30 minutes 79.0 g of methyl caprylate (0.5 mol) was added dropwise to the reaction flask over 30 minutes, Then warmed to 50 ° C, After 2 hours of continuous reaction, The methanol solvent was distilled off under reduced pressure, Then add 400mL of water, cooled to 0 , Control the internal temperature does not exceed 10 , With 10percent hydrochloric acid to adjust the pH of the reaction system to 3 to 4, Precipitated octanoic acid hydroxamic acid as a white solid, Filtered, washed, dried, 66.0 g of octanoic acid hydroxamic acid was obtained (yield: 83.0percent),
80.3%
With hydroxyammonium sulfate; calcium oxide In methanol at 50℃; for 2 h;
At 0 to 10 ° C,16.8 g quick lime (0.3 mol) was added in portions to a reaction flask containing 49.2 g hydroxylamine sulphate (0.3 mol) and 200 g methanol,Keep the internal temperature does not exceed 10 ,Lime plus life to be completed,Continue to react for 30 minutes,Filter to remove calcium sulfate solids,To the filtrate, 16.8 g of quick lime (0.3 mol) and 79 g of methyl caprylate (0.5 mol) were sequentially added,Then warmed to 50 ° C,After 2 hours of reaction,The methanol solvent was distilled off under reduced pressure,Then add 400g of water,Cooled to 0 ,Control the internal temperature does not exceed 10 ,With 10percent hydrochloric acid to adjust the pH of the system to 3 ~ 4,Precipitated octanoic acid hydroxamic acid as a white solid,filter,Washed,dry,63.8 g of octanoic acid hydroxamic acid was obtained (yield 80.3percent),
Reference：
[1] Patent: CN106966925, 2017, A, . Location in patent: Paragraph 0021; 0024; 0025; 0026; 0027; 0028
[2] Patent: CN106905190, 2017, A, . Location in patent: Paragraph 0020; 0021
[3] Patent: CN106699602, 2017, A, . Location in patent: Paragraph 0020; 0021; 0022; 0023; 0024; 0025; 0026-0031
[4] Patent: CN106854166, 2017, A, . Location in patent: Paragraph 0023; 0024; 0025; 0026; 0027; 0028; 0029-0036
[5] Patent: CN104592056, 2016, B, . Location in patent: Paragraph 0014; 0015
3
[ 111-11-5 ]
[ 7377-03-9 ]
[ 124-07-2 ]
Yield
Reaction Conditions
Operation in experiment
84%
With hydroxylamine nitrate; sodium hydroxide In methanol at 0 - 50℃; for 3 h;
44 g of sodium hydroxide (1.1 mol) was added portionwise at 0 to 10 ° C to a solution containing 53 g of hydroxylamine nitrate (0.55 mol) And 200 mL of methanol in the reaction flask. After all the addition of sodium hydroxide was added, the reaction was continued for 30 minutes. 79 g of methyl octanoate (0.5 mol) was added dropwise to the reaction flask over 30 minutes, and then the temperature was raised to 50 ° C and reacted for 2 hours. After the reaction, drop to the room Warm, filtered to obtain by-product of sodium nitrate, and then distilled to remove methanol (GC showed a small amount of methyl octanoate), the temperature dropped to 0 , And then slowly add 5percent nitric acid, adjust the pH value of 3 to 4, precipitation of solid, filter, filter cake dried octanoyl hydroxamic acid 67g, the yield 84percent
Reference：
[1] Patent: CN106588697, 2017, A, . Location in patent: Paragraph 0016-0017
4
[ 124-07-2 ]
[ 7377-03-9 ]
Reference：
[1] Monatshefte fur Chemie, 2000, vol. 131, # 6, p. 549 - 569
[2] Journal of Biological Chemistry, 1945, vol. 161, p. 416
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 7, p. 1624 - 1626
5
[ 629-37-8 ]
[ 7377-03-9 ]
Reference：
[1] Journal of Organic Chemistry, 1982, vol. 47, # 27, p. 5283 - 5289
[2] Synthesis, 1980, # 8, p. 654 - 656
[3] Journal of Organic Chemistry, 1982, vol. 47, # 27, p. 5283 - 5289
[4] Journal of the American Chemical Society, 1981, vol. 103, # 23, p. 7003 - 7005
[5] Journal of the American Chemical Society, 1981, vol. 103, # 23, p. 7003 - 7005
6
[ 71478-41-6 ]
[ 7377-03-9 ]
Reference：
[1] Organic and Biomolecular Chemistry, 2006, vol. 4, # 22, p. 4178 - 4185
29.13g n-octanoic acid (content 99%)And 21.05 g of acetic anhydride (content 97%) was added to the ball mill jar,Grinding for 10 min,Then add 14.11g hydroxylamine hydrochloride (content 98.5%),After continuing to grind for 40 minutes,Get a white solid product,It is the target collector product.After analysis and testing,The content of n-octyl hydroxydecanoic acid is 50.21%,Based on n-octanoic acidN-octyl hydroxamic acidThe yield was 95.81%.
With hydroxylamine hydrochloride; potassium hydroxide; In ethanol; water; at 5 - 55℃; for 3h;
To the 1000 mL four-necked flask was added hydroxylamine hydrochloride(48.7 g, 0.70 mol, 1.4 eq), water (50 g),Ethanol (200 g, 2.3X), stirred at room temperature until hydroxylamine hydrochloride was dissolved,Then joinEthyl octanoate(86.7 g, 0.5 mol, 1.0 eq), Stirred at room temperature to form a two-phase system, and then cooled to 5 ~ 10 ,Slowly add 40% KOH (168 g, 1.2 mol, 2.4 eq), Dripping finished, and then heated to 50 ~ 55 , insulation reaction 3 h,GC in the control of n-octanoic acid ethyl ester raw materials disappeared, stop the reaction,Cooled to 5-10 C, concentrated hydrochloric acid (90 mL) was added slowly,Adjust the pH = 6.4 ~ 6.7, precipitate a large number of white solid, filter,Dried at 50 for 8 h, the crude product was recrystallized from benzene,A white flocculent solid was 78.8 g, yield 91.1%
Example 3Rearrangement of octylhydroxamic Acid to benzyl-oxycarbonyl heptyl-amine1 mol of octylhydroxamic acid and 2 mol of triethylamine were introduced into 50 ml of ethyl acetate and cooled to 0 C. 1.2 mol of T3P (solution in ethyl acetate (50% w/w) were metered in while maintaining the reaction temperature, followed by stirring at this temperature for a further three hours. 1.2 mol of benzyl alcohol were added, and the reaction mixture was stirred at 60 C. for a further hour. At this time, GC of the reactions indicated a conversion of 100%. After warming to room temperature, 180 ml of water were added and the phases were separated. After the solvent had been condensed out, the product remained in a yield of 96%, HPLC purity 97% (a/a)
Example 4Rearrangement of octylhydroxamic Acid to tert-butyloxycarbonylheptylamine1 mol of octylhydroxamic acid and 2 mol of triethylamine were introduced into 50 ml of ethyl acetate and cooled to 0 C. 1.2 mol of T3P solution in ethyl acetate (50% w/w) were metered in while maintaining the reaction temperature, followed by stirring at this temperature for a further three hours. 1.2 mol of tert-butanol were added, and the reaction mixture was stirred at 60 C. for a further hour. At this time, GC of the reactions indicated a conversion of 100%. After warming to room temperature, 180 ml of water were added and the phases were separated. After the solvent had been condensed out, the product remained in a yield of 97%, GC purity 97% (a/a).
With hydroxylamine hydrochloride; sodium hydroxide; In methanol; water; at 5 - 40℃; for 5h;Large scale;
To the 500 L enamel reactor was added hydroxylamine hydrochloride (45.1 kg, 1.3 eq),Water (21 kg), methanol (84 kg, 1.06X),Stir at room temperature to hydroxylamine hydrochloride, and then add methyl octanoate(79.1 kg, 1.0 eq) and stirred at room temperature to form a two-phase system, Then cooled to 5 to 10 C, and 30% NaOH was slowly added (167 kg, 2.5 eq), the drop was completed, and then heated to 35 ~ 40 ,Incubation reaction 5 h, GC in the control of n-octanoic acid methyl ester raw material disappeared,Stop the reaction, cooling to 0 ~ 5 , slowly adding concentrated hydrochloric acid (110 kg),Adjust the pH = 6.4 ~ 6.7, precipitate a large number of white solid, filter,Dried at 50 for 8 h, the crude product was recrystallized from methanol,White flocculent solid 75.4 kg, yield 94.7%
85%
With hydroxylamine hydrochloride; triethylamine; In water; at 0 - 50℃; for 14.5h;
At 0 to 10 C, 116.4 g of triethylamine (1.15 mol) Was added dropwise to a solution containing 76.5 g of hydroxylamine hydrochloride (1. 1 mol) And 500 mL of water in a reaction flask, After all the addition of triethylamine, Continue to react for 30 minutes, 158.2 g of methyl octanoate (1.0 mol) was added dropwise to the reaction flask over 30 minutes and then heated to 50 C for 14 hours. After the completion of the reaction, the reaction was allowed to proceed to room temperature, and the filter cake was dried to give 135.3 g of octanoic acid. The yield was 85%, NMR (DMS0-d6, 400 MHz): delta 10.33 (br, 1 H), 8.64 (br, (T, 2H), 1.54-1.41 (m, 2H), 1.34-1.15 (m, 8H), 0.86 (t, 3H). 46 g of sodium hydroxide (1.15 mil) was added portionwise to the above filtrate at 0 to 10 (y, yielding 107.5 g of triethylamine oil).
83%
With hydroxylamine hydrochloride; calcium oxide; In methanol; at 10 - 50℃; for 2.5h;Autoclave;
Under low temperature stirring, 33.6 g quick lime (0.6 mol) was added in portions to a vial containing 41.7 g hydroxylamine hydrochloride (0.6 mol) And 200mL of methanol reaction flask, Keep the internal temperature does not exceed 10 , Lime to be added after all, Continue for 30 minutes 79.0 g of methyl caprylate (0.5 mol) was added dropwise to the reaction flask over 30 minutes, Then warmed to 50 C, After 2 hours of continuous reaction, The methanol solvent was distilled off under reduced pressure, Then add 400mL of water, cooled to 0 , Control the internal temperature does not exceed 10 , With 10% hydrochloric acid to adjust the pH of the reaction system to 3 to 4, Precipitated octanoic acid hydroxamic acid as a white solid, Filtered, washed, dried, 66.0 g of octanoic acid hydroxamic acid was obtained (yield: 83.0%),
80.3%
With hydroxyammonium sulfate; calcium oxide; In methanol; at 50℃; for 2h;
At 0 to 10 C,16.8 g quick lime (0.3 mol) was added in portions to a reaction flask containing 49.2 g hydroxylamine sulphate (0.3 mol) and 200 g methanol,Keep the internal temperature does not exceed 10 ,Lime plus life to be completed,Continue to react for 30 minutes,Filter to remove calcium sulfate solids,To the filtrate, 16.8 g of quick lime (0.3 mol) and 79 g of methyl caprylate (0.5 mol) were sequentially added,Then warmed to 50 C,After 2 hours of reaction,The methanol solvent was distilled off under reduced pressure,Then add 400g of water,Cooled to 0 ,Control the internal temperature does not exceed 10 ,With 10% hydrochloric acid to adjust the pH of the system to 3 ~ 4,Precipitated octanoic acid hydroxamic acid as a white solid,filter,Washed,dry,63.8 g of octanoic acid hydroxamic acid was obtained (yield 80.3%),
In 500L enamel reactor was added hydroxylamine hydrochloride 100kg, at room temperature was added an aqueous solution of an amount of 120kg 80% methanol, stirred at room temperature for 10 minutes at a rate of 70rpm. 130kg methyl n-octanoate then added, the mixture was stirred for 30 minutes. The solid was then added 0.1kg of 4-dimethylaminopyridine, and then controlling the temperature of about 5 C and added slowly solid NaOH 40kg, adjusted to pH 5.0, temperature 20 degrees, the reaction was stirred for 1 hour, then cooled to 0 degrees, centrifugation sodium chloride separated and removed, after the temperature set at 50 C, and thefiltrate concentrated in vacuo to a viscous, cooling crystallization, centrifugation content of 90% was crude. The 100kg of crude product was dissolved in 150kg ofmethanol, recrystallization, centrifugal separation,, at 50 degrees dried atunder reduced pressure to obtain N-Hydroxy -octanamide, Content of 99.2%.
With dodecyltrimethylammonium bromide; In aq. buffer; at 26.84℃;pH 9.2;
All reactions were performed at 300 K with a Thermo Fisher Evolution 300 UV-Visible spectrophotometer being equipped for temperature control (Peltier). All the kinetic runs were followed under pseudo-first-order conditions in which the concentration of nucleophile was at least 10 times more than substrates. The additions of nucleophile and substrate were done under thermal control at 300 K. The cuvettes were allowed to equilibrate thermally (300 K) in the cell holder for 30 min. After temperature equilibrium, the stock solutions of substrates were added to each cuvette and kinetic runs were started. The initial concentration of substrates in the cuvettes was 1.0 × 10-4 M. The rates constant (kobs) of nucleophilic reaction with paraoxon were determined by following the increase in absorption of p-nitrophenoxide anion at 400 nm. All the kinetic experiments were performed at an ionic strength of 0.1 M (with KCl). Borate buffer was employed as reaction medium. For all the kinetic runs, the absorbance/time results fit very well in the first-order rate Eq. (1).
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;
To a stirred solution of Salinomycin (1.0 equiv) in anhydrous CH2Cl2 at r.t., were added dicyclohexylcarbodiimide (DCC, 2.0 equiv) and 4-dimethylaminopyridine (DMAP, excess), followed by addition of hydroxamic (5.0 equiv) in one portion. The resulting solution was stirred overnight, then diluted with CH2Cl2 and washed with saturated NH4Cl. The organic layer was separated, died using a phase separator, and concentrated under reduced pressure to give a yellow oil. Acetone was added to the residues, then the resulting solution was stand in ice bath for 30min followed by filtration. The filtrate was collected and concentrated under reduced pressure. Purification by chromatography (Petrol ether/EtOAc =4/1) with silica gel afforded the salinomycin-hydroxamic acid conjugate.
In an air atmosphere, 10 ml of erythromycin thiocyanate was added to a 100 ml two-necked flask,12 mmol N-hydroxy octanamide and 50 ml acetonitrile were added, and after stirring at room temperature for 10 minutes, 5 mmol of concentrated sulfuric acid was added dropwise,The overhead tube was then heated to 80 C with an oil bath under magnetic stirring for 16 hours. Remove the oil bath,To the reaction solution was added 20 ml of water, extracted with 60 ml of ethyl acetate three times,The organic phases were combined and dried over anhydrous MgSO4 for 30 minutes. The filtrate was evaporated to dryness with a rotary evaporator,With NaOH solution to adjust the pH value of the solution to 10 ~ 12, precipitation precipitation, filtration,Dried to give erythromycin 6, 9 imine ether product in 90% yield.
With hydroxylamine nitrate; sodium hydroxide; In methanol; at 0 - 50℃; for 3h;
44 g of sodium hydroxide (1.1 mol) was added portionwise at 0 to 10 C to a solution containing 53 g of hydroxylamine nitrate (0.55 mol) And 200 mL of methanol in the reaction flask. After all the addition of sodium hydroxide was added, the reaction was continued for 30 minutes. 79 g of methyl octanoate (0.5 mol) was added dropwise to the reaction flask over 30 minutes, and then the temperature was raised to 50 C and reacted for 2 hours. After the reaction, drop to the room Warm, filtered to obtain by-product of sodium nitrate, and then distilled to remove methanol (GC showed a small amount of methyl octanoate), the temperature dropped to 0 , And then slowly add 5% nitric acid, adjust the pH value of 3 to 4, precipitation of solid, filter, filter cake dried octanoyl hydroxamic acid 67g, the yield 84%
With potassium chloride; N,N-didodecyl-N,N-dimethylammonium bromide; In aq. buffer; at 26.84℃;pH 9.2;Kinetics;
General procedure: All reactions were performed at 300 K with an Evolution 300 Thermo Scientific UV-visible spectrophotometer equipped with a Peltier thermal controller. All the kinetic runs were followed under pseudofirst-order conditions in which the concentration of the nucleophiles was at least 10 times higher than the initial concentration of the substrates. The rates of nucleophilic reaction with the esters were determined by following the increase in absorption of the p-nitrophenoxide anion at 400 nm. All kinetic experiments were performed at an ionic strength of 0.1 M (with KCl). Phosphate and borate buffers were employed. For all of the kinetic runs, the absorbance/time results fitted very well with the first-order rate equation. ln(A? - At) = ln(A? - A0) - k The pseudofirst-order rate constants (kobs) were obtained from linear plots of log (A? - At) versus time. The spectrum shows (Fig. 1) an increase in absorbance at 400 nm with the formation of the p-nitrophenoxide ion during the course of the reaction.
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