* 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 sodium hydroxide In water at 0 - 20℃; for 1 h;
In the reaction vessel, sodium glutamate 18.73g (0.11mol), water, 75g, stirring with 1mol / L aqueous sodium hydroxide solution of PH = 8, and slowly added dropwise at 0 28.31g step (1) of the resulting dichloroethane, nitrobenzene chloride solution, was dropwise added to 1mol / L aqueous sodium hydroxide to adjust the PH value of the reaction system was kept PH = 8, the reaction solution changed from white to purple discoloration, the addition was complete 1 hour reaction at room temperature, static layers were separated and the organic layer was extracted twice with water, the combined aqueous layer was acidified with hydrochloric PH = 1, the precipitated crystals were filtered and dried to give N- Nitrobenzoylhydrazone -L- glutamic acid 29.81 g, HPLC purity of 98.43percent, a yield of 99.03percent (with on-nitro benzoic acid).
Reference：
[1] Patent: CN105439895, 2016, A, . Location in patent: Paragraph 0027; 0028
2
[ 122-04-3 ]
[ 32221-81-1 ]
[ 6758-40-3 ]
Yield
Reaction Conditions
Operation in experiment
29.3 g
Stage #1: With sodium hydroxide In water Stage #2: at 5℃;
2 Add 75g of water and 16.9g of sodium glutamate (0.1mol) to the reaction unit, adjust the pH to 8 with a 1mol/L sodium hydroxide solution with stirring, then cool to 5±1°C, slowly add dropwise The solution containing p-nitrobenzoyl chloride obtained in the step 1 was maintained at pH = 8 during the dropwise addition, and the reaction was completed until the temperature was 5 ± 1 ° C. After completion of the reaction, the pH was adjusted to 1 with dilute hydrochloric acid, crystallized, filtered, and the filter cake was washed with water and dried under reduced pressure to give 29.3 g of N-p-nitrobenzoyl-L-glutamic acid with a purity of 99.4percent ( HPLC), a two-step yield of 99.0percent based on p-nitrobenzoic acid.
Reference：
[1] Patent: CN108147977, 2018, A, . Location in patent: Paragraph 0015; 0017; 0018; 0021; 0022; 0024
Reference：
[1] Patent: CN105439895, 2016, A,
[2] Patent: CN108147977, 2018, A,
5
[ 7148-24-5 ]
[ 6758-40-3 ]
Reference：
[1] Journal of the Chemical Society, 1949, p. 1401,1404
[2] Journal of the Chemical Society, 1949, p. 1401,1404
6
[ 122-04-3 ]
[ 6758-40-3 ]
Reference：
[1] Journal of the Chemical Society, 1949, p. 1401,1404
7
[ 6758-40-3 ]
[ 4271-30-1 ]
Yield
Reaction Conditions
Operation in experiment
96.58%
With palladium 10% on activated carbon; ammonium formate In methanol at 20℃; for 0.5 h;
Reaction vessel was added N- Nitrobenzoylhydrazone -L- glutamic acid 27.23g (0.1mol), methanol 118g, turn on stirring, was added 10percent Pd / C0.59g, then slowly added ammonium formate 18.92g (0.3mol), stirred at room temperature for 30 minutes, filtered, recovered Pd / C next applied, the filtrate was adjusted with hydrochloric acid in methanol PH = 3, the precipitated crystals were filtered after 30 minutes resting, a small amount of methanol, washed, dried, to give N - amino-benzoyl -L- glutamic acid 25.75g, HPLC purity of 99.88percent, a yield of 96.58percent, the total yield of 95.64percent (with on-nitro benzoic acid).
25.7 g
With iron(III) chloride hexahydrate; hydrazine hydrate In methanol at 20℃;
3 Add 29.3 g of N-p-nitrobenzoyl-L-glutamic acid obtained in Step 2, 118 g of methanol, and 0.81 g of ferric chloride hexahydrate (0.003 mol) to the reaction apparatus, and slowly drip with stirring. 15.0 g of hydrazine hydrate (0.3 mol) was added, and the reaction was stirred to completion at room temperature. After completion of the reaction, the pH was adjusted to 3.5 with hydrochloric acid, crystallized, filtered, and the filter cake was washed with methanol, and then dried under reduced pressure to give 25.7 g of N-p-aminobenzoyl-L-glutamic acid with a purity of 99.95percent (HPLC) The three-step yield based on p-nitrobenzoic acid was 96.6percent.
Reference：
[1] Patent: CN105439895, 2016, A, . Location in patent: Paragraph 0029; 0030
[2] Chirality, 2010, vol. 22, # 2, p. 252 - 257
[3] Journal of the Chemical Society, 1949, p. 1401,1404
[4] Yakugaku Zasshi, 1949, vol. 69, p. 457[5] Chem.Abstr., 1950, p. 3442
[6] Chemische Berichte, 1951, vol. 84, p. 485,488[7] Zeitschrift fuer Naturforschung, 1950, vol. 5b, p. 132,135
[8] Patent: US2560616, 1948, ,
[9] Recueil des Travaux Chimiques des Pays-Bas, 1951, vol. 70, p. 738,741
[10] J. Immunol., 1935, vol. 29, p. 371,373
[11] Pharmaceutical Chemistry Journal, 1985, vol. 19, # 4, p. 273 - 275[12] Khimiko-Farmatsevticheskii Zhurnal, 1985, vol. 19, # 4, p. 448 - 450
[13] Patent: CN108147977, 2018, A, . Location in patent: Paragraph 0015; 0019; 0020; 0021; 0022; 0024
8
[ 918-00-3 ]
[ 6758-40-3 ]
[ 2387-48-6 ]
[ 59-30-3 ]
Yield
Reaction Conditions
Operation in experiment
80%
Stage #1: With hydrogen In water at 82℃; Stage #2: With sodium metabisulfite; sodium hydroxide In water at 45℃;
296 g (1 mol) of p-nitrobenzoylglutamic acid and 162.8 g (1.05 mol) of 2,4-diamino-6-hydroxy-5-nitrosopyrimidine were dissolved in 2000 mL of water and heated to 82 ° C , Dissolved under stirring, added 1.2g Lenny nickel catalyst, nitrogen and airGas replacement three times, hydrogen and nitrogen replacement three times, hydrogen pressure maintained at 0.8MPa, until the end of hydrogen absorption, hydrogenation after(1.1 mol) of sodium metabisulfite was added to the filtrate, and 1184.3 g (1.1 mol) of a 15percent aqueous trichloroacetone solution was added dropwise at 45 ° C, and the mixture was adjusted with 10percent by mass of sodium hydroxide solution PH maintained at around 4.5, the reaction finishedAfter completion, cool down to 0 crystallization, pressure filtration, get crude folic acid. And then refined to obtain yellow folic acid solid powder. The total yield of folic acid was 80percent and the product content was 98.7percent.
Reference：
[1] Patent: CN106279174, 2017, A, . Location in patent: Paragraph 0023; 0024; 0025; 0026; 0027; 0028; 0029-0031
With palladium 10% on activated carbon; ammonium formate; In methanol; at 20℃; for 0.5h;
Reaction vessel was added N- Nitrobenzoylhydrazone -L- glutamic acid 27.23g (0.1mol), methanol 118g, turn on stirring, was added 10% Pd / C0.59g, then slowly added ammonium formate 18.92g (0.3mol), stirred at room temperature for 30 minutes, filtered, recovered Pd / C next applied, the filtrate was adjusted with hydrochloric acid in methanol PH = 3, the precipitated crystals were filtered after 30 minutes resting, a small amount of methanol, washed, dried, to give N - amino-benzoyl -L- glutamic acid 25.75g, HPLC purity of 99.88%, a yield of 96.58%, the total yield of 95.64% (with on-nitro benzoic acid).
25.7 g
With iron(III) chloride hexahydrate; hydrazine hydrate; In methanol; at 20℃;
3 Add 29.3 g of N-p-nitrobenzoyl-L-glutamic acid obtained in Step 2, 118 g of methanol, and 0.81 g of ferric chloride hexahydrate (0.003 mol) to the reaction apparatus, and slowly drip with stirring. 15.0 g of hydrazine hydrate (0.3 mol) was added, and the reaction was stirred to completion at room temperature. After completion of the reaction, the pH was adjusted to 3.5 with hydrochloric acid, crystallized, filtered, and the filter cake was washed with methanol, and then dried under reduced pressure to give 25.7 g of N-p-aminobenzoyl-L-glutamic acid with a purity of 99.95% (HPLC) The three-step yield based on p-nitrobenzoic acid was 96.6%.
296 g (1 mol) of p-nitrobenzoylglutamic acid and 162.8 g (1.05 mol) of 2,4-diamino-6-hydroxy-5-nitrosopyrimidine were dissolved in 2000 mL of water and heated to 82 C , Dissolved under stirring, added 1.2g Lenny nickel catalyst, nitrogen and airGas replacement three times, hydrogen and nitrogen replacement three times, hydrogen pressure maintained at 0.8MPa, until the end of hydrogen absorption, hydrogenation after(1.1 mol) of sodium metabisulfite was added to the filtrate, and 1184.3 g (1.1 mol) of a 15% aqueous trichloroacetone solution was added dropwise at 45 C, and the mixture was adjusted with 10% by mass of sodium hydroxide solution PH maintained at around 4.5, the reaction finishedAfter completion, cool down to 0 crystallization, pressure filtration, get crude folic acid. And then refined to obtain yellow folic acid solid powder. The total yield of folic acid was 80% and the product content was 98.7%.
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