Reference：
[1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1983, vol. 37, # 10, p. 879 - 890
2
[ 4205-23-6 ]
[ 56-40-6 ]
[ 1192-79-6 ]
[ 1121-78-4 ]
[ 1121-25-1 ]
[ 1072-83-9 ]
Reference：
[1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1983, vol. 37, # 10, p. 879 - 890
3
[ 4429-05-4 ]
[ 56-40-6 ]
[ 1192-79-6 ]
[ 1121-78-4 ]
[ 1121-25-1 ]
[ 1072-83-9 ]
Reference：
[1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1983, vol. 37, # 10, p. 879 - 890
4
[ 492-62-6 ]
[ 56-87-1 ]
[ 56-40-6 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13925-00-3 ]
[ 13360-65-1 ]
[ 17398-16-2 ]
[ 13925-07-0 ]
[ 13925-09-2 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708
5
[ 77287-34-4 ]
[ 156-81-0 ]
[ 849585-22-4 ]
[ 617-48-1 ]
[ 2491-15-8 ]
[ 110-15-6 ]
[ 108-53-2 ]
[ 71-30-7 ]
[ 113-00-8 ]
[ 127-17-3 ]
[ 66-22-8 ]
[ 66224-66-6 ]
[ 56-40-6 ]
[ 302-72-7 ]
[ 18514-52-8 ]
Yield
Reaction Conditions
Operation in experiment
0.18 mg
With ferric sulfate nonahydrate In water at 80℃; for 24 h;
General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
With copper(II) choride dihydrate In water at 80℃; for 24 h;
General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
General procedure: Sodium carbonate (Na2CO3, 1.590g, 15mmol) was added to a solution of amino acids (2a-h, 12.5mmol) in water (15mL) with continuous stirring until all the solutes had dissolved. The solution was cooled to−5°C and the appropriate benzenesulphonyl chloride (1a-c, 15mmol) was added in four portions over a period of 1h. The slurry was further stirred at room temperature for about 4h. The progress of the reaction was monitored using TLC (MeOH/DCM, 1:9). Upon completion, the mixture was acidified using 20percent aqueous hydrochloric acid to pH 2. The crystals was filtered via suction and washed with pH 2.2 buffer. The pure products (3a-x) were dried over self-indicating fused silica gel in a desiccator. 2.2.1 2-(4-methylphenylsulphonamido) acetic acid (3a) The amino acid was glycine, yield (2.8410g, 99.34percent), mp, 88.4–88.6°C, FTIR (KBr, cm−1): 3448 (OH of COOH), 3277 (NH), 2957 (C-H aliphatic), 1730 (C=O), 1598, 1440 (C=C), 1354, 1321 (2S=O), 1185 (SO2-NH), 1111, 1094 (C-N, C-O). 1H NMR (DMSO-d6)δ: 7.90–7.88 (t, J=6.3Hz, 1H, NH), 7.65–7.63 (d, J=8.6Hz, 2H, ArH), 7.34–7.33 (d, J=8.05Hz, 2H, ArH), 3.52–3.51 (d, J=5.7Hz, CH2), 2.34 (s, 3H, CH3). 13C NMR (DMSO-d6)δ: 170.7 (C=O), 143.1, 138.4, 130.0, 127.1 (aromatic carbons), 44.3 (CH2), 21.5 (CH3). HRMS-ESI (m/z): 228.0412 (M-H)-, calculated, 228.0408.
99.34%
With sodium carbonate In water for 4 h;
General procedure: Sodium carbonate (Na2CO3, 1.590 g, 15 mmol) was added to a solution of amino acids (6a-h,12.5 mmol) in water (15 mL) with continuous stirring until all the solutes dissolved. The solutionwas cooled to -5°C and an appropriate benzenesulphonyl chloride (5a-c, 15 mmol) wasadded in four portions over a period of 1 h. The slurry was further stirred at room temperaturefor 4 h. The progress of the reaction was monitored by using TLC (MeOH/DCM, 1:9). Uponcompletion, the mixture was acidified using 20percent aqueous hydrochloric acid to pH 2. The crystalswas filtered via suction and washed with pH 2.2 buffer. The pure products (7a-x) weredried over self-indicating fused silica gel in a desiccator. 2-(4-methylphenylsulphonamido) acetic acid (7a). The amino acid was glycine, yield(2.8410 g, 99.34percent), appearance white needles, mp, 88.4-88.6°C, FTIR (KBr, cm-1): 3448 (OHof COOH), 3277 (NH), 2957 (C-H aliphatic), 1730 (C = O), 1598, 1440 (C = C), 1354, 1321(2S = O), 1185 (SO2-NH), 1111, 1094 (C-N, C-O). 1H NMR (500 MHz, DMSO-d6) δ: 7.89 (t,J = 6.3 Hz, 1H, NH), 7.64 (d, J = 8.6 Hz, 2H, ArH), 7.33 (d, J = 8.05 Hz, 2H, ArH), 3.51 (d,J = 5.7 Hz, CH2), 2.34 (s, 3H, CH3). 13C NMR (500 MHz, DMSO-d6) δ: 170.8 (C = O), 143.1, 138.4, 130.0, 127.1 (aromatic carbons), 44.3 (CH2), 21.5 (CH3). HRMS-ESI (m/z): 228.0410(M-H)-, calculated, 228.0408.
86%
With sodium hydrogencarbonate In water; acetone at 25℃; for 0.25 h;
General procedure: Sulfonyl chloride (0.20 mmol) was dissolved in acetone (2 mL) and the resulting solution was injected in the reagent loop A. An aqueous NaHCO3 0.4 M (1 mL) was added to a solution of the amine (0.22 mmol) dissolved in PEG-400 (1 mL). The H2O/PEG400 solution (2 mL, 1:1,v/v) was then injected in the reagent loop B. A degassed solution of acetone and water were connected with pump A and B, respectively, and the flow rate was fixed at 0.5 mL min−1 (0.25 mL min−1 + 0.25 mL min−1). After switching the sample loops, the mixtures exited were joined in a T-piece, entered in a 10 mL PTFE coil reactor warmed at 25 °C, fitted with the back pressure regulator (100 psi), directed in UV detector and the output was recovered in a fraction collector. The reaction mixture was drooped in a tube containing Et2O/HCl 3 N (5 mL, 4:1, v/v). The two phases were separated, and the organic one was washed with H2O (2 × 1 mL), dried over Na2SO4, and concentrated under reduced pressure to give the desired pure compound.
81%
at 20 - 25℃;
General procedure: Syntheses of G1 and P1: To a stirred solution of glycine (0.75 g, 10.0 mmol) or l-phenylalanine (1.65 g, 10.0 mmol) in 20 mL of 1 M NaOH solution at 25 °C, p-toluenesulfonyl chloride (1.91 g, 10.0 mmol) was added. After overnight stirring at room temperature, the solid residue was filtered off and the aqueous reaction portion was acidified with 1 M HCl. The obtained solid was filtered and purified by column chromatography on silica with hexane and EtOAc (1:2) to obtain compounds G1 and P1 as white solids. (Yields, 81percent and 76percent, respectively.) Compound G1: Yield 81percent as white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.66 (broad singlet, 1H, -COOH), 7.93 (t, J = 6.1 Hz, 1H, -NH-), 7.67 (d, J = 8.4 Hz, 2H, ArH), 7.37 (d, J = 8.3 Hz, 2H, ArH), 3.54 (d, J = 6.1 Hz, 2H, -CH2-), 2.37 (s, 3H, -CH3) ppm. 13C NMR (100 MHz, CDCl3): δ 171.1, 143.8, 136.3, 129.9, 127.3, 40.3, 21.6 ppm. Anal. Calcd [C9H11NO4S]: C, 47.15; H, 4.84; N, 6.11; S, 13.99. Found: C, 48.36; H, 5.11; N, 5.93; S, 14.27.
72%
Stage #1: With sodium carbonate In water at 70 - 85℃; for 0.75 h; Stage #2: With hydrogenchloride In water at 20℃;
General procedure: The nitrogen tosylation was done using a reported procedure. In a round bottom flask, 2.4 equiv. of Na2CO3 was dissolved in 70 °C water (C = 0.66 mol/L). Then 1.0 equiv. of the desired anthranilic acid was added followed by 1.4 equiv. of tosyl chloride. The suspension was stirred at 70 °C for 40 min then at 85 °C for 5 min. The reaction mixture was then directly filtrated and the solid washed with 85 °C water. The filtrate was cooled to room temperature and then acidified to pH = 1 using an aqueous 6M HCl solution. The precipitated solid was collected by suction and dried over vacuum. The resulting tosyl anthranilic acids were used without further purification.
21%
Stage #1: With sodium hydroxide In diethyl ether; water at 20℃; for 3.16667 h; Stage #2: With hydrogenchloride In water
Glycine (1 g, 13.32 mmol) was dissolved in IN NaOH (aq.) and a solution of tosyl chloride (2.62 g, 13.72 mmol) in diethyl ether (15 ml) was added portion wise with stirring over 10 min. The resulting mixture was allowed to stir at room temperature for 3 h. The ethereal layer was separated and the aqueous layer treated with 2N HCl solution until acidified to pH 5. After cooling the resulting solution to 0 0C, the product began to precipitate from the solution. The solid was collected by filtration and the mother liquor placed in a fridge overnight causing more of the desired product to precipitate. The solid was again collected by filtration and the combined collected solid was dried under high vacuum affording 9 as a white powder (613 mg, 21percent). δH (400 MHz, MeOD) 2.41 (3H, s, CH3), 3.66 (2H, S5 CH2), 7.35 (2H, d, J=8 Hz5 ArH)5 7.73 (2H5 d, J=8 Hz, ArH); δc (100.6 MHz, MeOD) 20.3, 43.6, 127.0, 129.5, 137.6, 143.6, 171.0; MS (ES+) 246.8 (100percent, [M+H20]+); MS (ES') 227.9 (100percent, [M-H]-); HRMS [M-H]' requires 228.03360, found 228.03364.
Reference：
[1] European Journal of Medicinal Chemistry, 2017, vol. 135, p. 349 - 369
[2] PLoS ONE, 2018, vol. 13, # 1,
[3] Journal of the American Chemical Society, 2018, vol. 140, # 17, p. 5834 - 5841
[4] Journal of Molecular Catalysis A: Chemical, 2011, vol. 351, p. 41 - 45
[5] Organic and Biomolecular Chemistry, 2018, vol. 16, # 31, p. 5618 - 5625
[6] Catalysis Communications, 2011, vol. 12, # 15, p. 1477 - 1482
[7] European Journal of Organic Chemistry, 2007, # 35, p. 5909 - 5916
[8] ACS Combinatorial Science, 2013, vol. 15, # 5, p. 235 - 239
[9] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 15, p. 3422 - 3425
[10] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000, vol. 55, # 2, p. 203 - 207
[11] Advanced Synthesis and Catalysis, 2007, vol. 349, # 11-12, p. 1873 - 1876
[12] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 23, p. 7353 - 7358
[13] Synthesis (Germany), 2016, vol. 48, # 21, p. 3719 - 3729
[14] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 12, p. 2635 - 2641
[15] Asian Journal of Chemistry, 2013, vol. 25, # 8, p. 4401 - 4403
[16] Agricultural and Biological Chemistry, 1985, vol. 49, # 4, p. 973 - 980
[17] Journal of Pharmaceutical Sciences, 1987, vol. 76, # 2, p. 149 - 152
[18] Patent: WO2007/136858, 2007, A2, . Location in patent: Page/Page column 66
[19] Justus Liebigs Annalen der Chemie, 1913, vol. 398, p. 118
[20] Journal of the American Chemical Society, 1937, vol. 59, p. 1116
[21] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 9, p. 3244 - 3254
[22] Bulletin of the Chemical Society of Japan, 1996, vol. 69, # 12, p. 3639 - 3650
[23] European Journal of Medicinal Chemistry, 2000, vol. 35, # 3, p. 299 - 307
[24] Tetrahedron Letters, 2001, vol. 42, # 4, p. 665 - 667
[25] Heteroatom Chemistry, 2002, vol. 13, # 4, p. 316 - 323
[26] Organic Letters, 2006, vol. 8, # 4, p. 633 - 636
[27] Patent: US2002/151546, 2002, A1,
[28] Journal of Coordination Chemistry, 2011, vol. 64, # 10, p. 1695 - 1706
[29] Organic and Biomolecular Chemistry, 2012, vol. 10, # 9, p. 1735 - 1738
[30] Journal of Coordination Chemistry, 2012, vol. 65, # 2, p. 239 - 250
[31] Journal of Coordination Chemistry, 2012, vol. 65, # 18, p. 3160 - 3173
[32] Organic Letters, 2016, vol. 18, # 4, p. 740 - 743
[33] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 11, p. 2567 - 2575
[34] Advanced Synthesis and Catalysis, 2016, vol. 358, # 9, p. 1385 - 1391
[35] Advanced Synthesis and Catalysis, 2016, vol. 358, # 12, p. 1968 - 1974
[36] Synthetic Communications, 2016, vol. 46, # 15, p. 1299 - 1306
[37] PLoS ONE, 2017, vol. 12, # 9,
[38] European Journal of Organic Chemistry, 2018, vol. 2018, # 8, p. 1067 - 1070
[39] European Journal of Medicinal Chemistry, 2018, vol. 150, p. 87 - 101
[40] Lipids in Health and Disease, 2018, vol. 17, # 1,
Reference：
[1] Acta Universitates Lundensis 28 <1892>, 2. Abt., Abhandl. III, S. 12,
14
[ 2232-08-8 ]
[ 56-40-6 ]
[ 288-32-4 ]
[ 1080-44-0 ]
Reference：
[1] Bulletin de la Societe Chimique de France, 1988, # 2, p. 356 - 360
15
[ 29981-92-8 ]
[ 56-40-6 ]
[ 1080-44-0 ]
[ 35487-17-3 ]
Reference：
[1] Bulletin de la Societe Chimique de France, 1988, # 2, p. 356 - 360
16
[ 51060-12-9 ]
[ 56-40-6 ]
[ 1080-44-0 ]
[ 34531-53-8 ]
Reference：
[1] Bulletin de la Societe Chimique de France, 1988, # 2, p. 356 - 360
17
[ 1812-30-2 ]
[ 1563-56-0 ]
[ 56-40-6 ]
Reference：
[1] Journal of Pharmaceutical Sciences, 1991, vol. 80, # 5, p. 459 - 468
18
[ 56-87-1 ]
[ 56-40-6 ]
[ 78-98-8 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 1124-11-4 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 14667-55-1 ]
[ 13925-07-0 ]
[ 22047-26-3 ]
[ 15707-34-3 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
19
[ 56-87-1 ]
[ 56-40-6 ]
[ 78-98-8 ]
[ 5910-89-4 ]
[ 13360-65-1 ]
[ 17398-16-2 ]
[ 13925-07-0 ]
[ 22047-26-3 ]
[ 22047-27-4 ]
[ 13360-64-0 ]
[ 15707-34-3 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708
20
[ 492-62-6 ]
[ 56-87-1 ]
[ 56-40-6 ]
[ 290-37-9 ]
[ 5910-89-4 ]
[ 13925-00-3 ]
[ 13360-65-1 ]
[ 17398-16-2 ]
[ 13925-07-0 ]
[ 13925-09-2 ]
[ 13925-08-1 ]
[ 13360-64-0 ]
[ 15707-34-3 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 18, p. 4697 - 4708
21
[ 100-07-2 ]
[ 56-40-6 ]
[ 13214-64-7 ]
Reference：
[1] Tetrahedron, 1984, vol. 40, # 2, p. 327 - 337
[2] Journal of Chemical Sciences, 2011, vol. 123, # 3, p. 335 - 341
[3] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 3, p. 1904 - 1924
[4] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1980, vol. 16, # 7, p. 701 - 703[5] Khimiya Geterotsiklicheskikh Soedinenii, 1980, # 7, p. 909 - 911
[6] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 6, p. 932 - 937
[7] Arzneimittel Forschung, 1954, vol. 4, p. 575,578
[8] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1980, vol. 16, # 7, p. 701 - 703[9] Khimiya Geterotsiklicheskikh Soedinenii, 1980, # 7, p. 909 - 911
[10] Journal of the American Chemical Society, 1980, vol. 102, # 22, p. 6828 - 6837
[11] Chemical & Pharmaceutical Bulletin, 1984, vol. 32, # 8, p. 3100 - 3104
[12] Journal of Medicinal Chemistry, 1989, vol. 32, # 5, p. 1033 - 1038
[13] Farmaco, 1998, vol. 53, # 6, p. 439 - 442
[14] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 37 - 41
[15] Patent: US2004/29884, 2004, A1, . Location in patent: Page/Page column 2
[16] Heterocycles, 2011, vol. 83, # 1, p. 153 - 161
[17] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4642 - 4647
[18] Biopharmaceutics and Drug Disposition, 2011, vol. 32, # 6, p. 343 - 354
[19] Synthetic Communications, 2013, vol. 43, # 11, p. 1538 - 1542
[20] Tetrahedron, 2013, vol. 69, # 34, p. 7019 - 7025
[21] Tetrahedron Letters, 2015, vol. 56, # 6, p. 851 - 855
[22] Medicinal Chemistry Research, 2016, vol. 25, # 6, p. 1239 - 1249
[23] Journal of the Chinese Chemical Society, 2016, vol. 63, # 11, p. 909 - 916
[24] Archiv der Pharmazie, 2017, vol. 350, # 8,
[25] Journal of Enzyme Inhibition and Medicinal Chemistry, 2018, vol. 33, # 1, p. 629 - 638
22
[ 56-40-6 ]
[ 155164-68-4 ]
[ 13214-64-7 ]
Reference：
[1] Synthesis, 2002, # 6, p. 733 - 738
23
[ 30364-57-9 ]
[ 56-40-6 ]
[ 6066-82-6 ]
[ 13214-64-7 ]
Reference：
[1] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3583 - 3586
24
[ 7464-46-2 ]
[ 56-40-6 ]
[ 100-02-7 ]
[ 13214-64-7 ]
Reference：
[1] Canadian Journal of Chemistry, 1998, vol. 76, # 6, p. 729 - 737
25
[ 122-01-0 ]
[ 56-40-6 ]
[ 13450-77-6 ]
Yield
Reaction Conditions
Operation in experiment
11.2 g
With sodium hydroxide In water at 15 - 26℃; for 1.5 h;
To a stirred and cooled (15 °C) solution of glycine (5.0 g, 66.602 mmol) in 10percent aqueous sodium hydroxide solution (50 mL) was added benzoyl chloride (11.8 mL, 92.57 mmol) in portions. The reaction mixture was stirred at RT for 1.5 h. The reaction mixture was poured in to crushed ice and acidified with conc. HC1 till pH 3-4.The obtained precipitate was collected by filtration and dried to yield 11.2 g of thetitle product as a solid. ‘H NMR (300 MHz, DMSO-d6) ö 4.08 (s, 2H), 7.49 (d, J = 8.7Hz, 2H), 7.85 (d, J = 8.1 Hz, 2H), 8.00 (d, J = 8.4 Hz, 1H).
Reference：
[1] Journal of Biological Chemistry, 1926, vol. 67, p. 557
[2] Naunyn-Schmiedebergs Archiv fuer Experimentelle Pathologie und Pharmakologie, 1931, vol. 161, p. 719,724
[3] Journal of the American Chemical Society, 1980, vol. 102, # 22, p. 6828 - 6837
[4] Chemical & Pharmaceutical Bulletin, 1984, vol. 32, # 8, p. 3100 - 3104
[5] Journal of Medicinal Chemistry, 1989, vol. 32, # 5, p. 1033 - 1038
[6] Journal of Medicinal Chemistry, 1997, vol. 40, # 12, p. 1771 - 1772
[7] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 37 - 41
[8] Journal of Chemical Research, 2006, # 11, p. 738 - 739
[9] Heterocycles, 2011, vol. 83, # 1, p. 153 - 161
[10] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4642 - 4647
[11] Oriental Journal of Chemistry, 2010, vol. 26, # 4, p. 1533 - 1536
[12] Biopharmaceutics and Drug Disposition, 2011, vol. 32, # 6, p. 343 - 354
[13] European Journal of Medicinal Chemistry, 2015, vol. 96, p. 425 - 435
[14] Patent: WO2015/159233, 2015, A1, . Location in patent: Page/Page column 70; 71
[15] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 13, p. 3043 - 3051
[16] Archiv der Pharmazie, 2018, vol. 351, # 2,
26
[ 50-00-0 ]
[ 56-40-6 ]
[ 1118-68-9 ]
Reference：
[1] Chemistry and Physics of Lipids, 1997, vol. 86, # 2, p. 171 - 181
[2] Tetrahedron Letters, 2007, vol. 48, # 43, p. 7680 - 7682
[3] Synthesis, 2011, # 3, p. 490 - 496
[4] Tetrahedron Letters, 1991, vol. 32, # 31, p. 3847 - 3848
[5] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 10, p. 3021 - 3025
[6] Yakugaku Zasshi, 1946, vol. 66, p. 4[7] Chem.Abstr., 1951, p. 7956
[8] Journal of the Chemical Society, 1950, p. 1342,1345
[9] Journal of the American Chemical Society, 1951, vol. 73, p. 864
[10] Journal of the American Chemical Society, 1933, vol. 55, p. 4576
[11] Journal of pharmaceutical sciences, 1969, vol. 58, # 10, p. 1228 - 1232
[12] Bulletin of the Chemical Society of Japan, 1968, vol. 41, # 7, p. 1679 - 1681
[13] Analytical Chemistry, 2007, vol. 79, # 22, p. 8631 - 8638
[14] Patent: US2013/78728, 2013, A1, . Location in patent: Sheet 4
[15] Journal of Mass Spectrometry, 2015, vol. 50, # 5, p. 771 - 781
27
[ 50-00-0 ]
[ 56-40-6 ]
[ 107-97-1 ]
[ 1118-68-9 ]
Reference：
[1] Biochemische Zeitschrift, 1913, vol. 51, p. 123
28
[ 50-00-0 ]
[ 64-18-6 ]
[ 56-40-6 ]
[ 1118-68-9 ]
[ 124-38-9 ]
[ 75-50-3 ]
Reference：
[1] Journal of the American Chemical Society, 1933, vol. 55, p. 4576
29
[ 50-00-0 ]
[ 64-19-7 ]
[ 56-40-6 ]
[ 1118-68-9 ]
[ 124-38-9 ]
[ 75-50-3 ]
Reference：
[1] Journal of the American Chemical Society, 1933, vol. 55, p. 4576
Reference：
[1] Angewandte Chemie - International Edition, 2001, vol. 40, # 10, p. 1948 - 1951
34
[ 556-56-9 ]
[ 56-40-6 ]
[ 54594-06-8 ]
[ 16338-48-0 ]
Reference：
[1] Angewandte Chemie - International Edition, 2001, vol. 40, # 10, p. 1948 - 1951
35
[ 106-95-6 ]
[ 56-40-6 ]
[ 16338-48-0 ]
Reference：
[1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1988, vol. 37, # 12, p. 2541 - 2544[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1988, # 12, p. 2818 - 2821
[3] Tetrahedron Asymmetry, 1998, vol. 9, # 12, p. 2121 - 2131
[4] Tetrahedron Asymmetry, 2010, vol. 21, # 24, p. 2956 - 2965
36
[ 638-45-9 ]
[ 56-40-6 ]
[ 106819-03-8 ]
[ 116783-26-7 ]
Reference：
[1] Angewandte Chemie - International Edition, 2001, vol. 40, # 10, p. 1948 - 1951
37
[ 56-40-6 ]
[ 108-12-3 ]
[ 16284-60-9 ]
Reference：
[1] Biochemische Zeitschrift, 1910, vol. 23, p. 500
38
[ 503-74-2 ]
[ 56-40-6 ]
[ 16284-60-9 ]
Reference：
[1] Biomedical Mass Spectrometry, 1979, vol. 6, # 10, p. 439 - 443
39
[ 56-40-6 ]
[ 6244-91-3 ]
[ 16284-60-9 ]
[ 85-61-0 ]
Reference：
[1] Drug Metabolism and Disposition, 2012, vol. 40, # 2, p. 346 - 352
40
[ 78-84-2 ]
[ 56-40-6 ]
[ 5817-22-1 ]
[ 10148-70-6 ]
Reference：
[1] Journal of the American Chemical Society, 1997, vol. 119, # 49, p. 11734 - 11742
[2] Tetrahedron, 2007, vol. 63, # 34, p. 8088 - 8093
Reference：
[1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1990, vol. 39, # 7.2, p. 1479 - 1485[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1990, # 7, p. 1630 - 1636
43
[ 56-40-6 ]
[ 456-41-7 ]
[ 19883-77-3 ]
[ 110117-84-5 ]
Reference：
[1] Angewandte Chemie - International Edition, 2001, vol. 40, # 10, p. 1948 - 1951
44
[ 56-40-6 ]
[ 74-88-4 ]
[ 107-43-7 ]
Reference：
[1] Journal of Mass Spectrometry, 2012, vol. 47, # 1, p. 79 - 88
45
[ 186581-53-3 ]
[ 56-40-6 ]
[ 107-43-7 ]
Reference：
[1] Chemische Berichte, 1950, vol. 83, p. 420,425,430
[2] Chemische Berichte, 1922, vol. 55, p. 1069
46
[ 56-40-6 ]
[ 107-43-7 ]
Reference：
[1] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1942, vol. 277, p. 97,105
[2] M.Florkin,H.S.Mason, Comaparative Biochemistry,Bd.1 <New York 1960>S.190/1,
47
[ 186581-53-3 ]
[ 60-29-7 ]
[ 7732-18-5 ]
[ 56-40-6 ]
[ 107-43-7 ]
Reference：
[1] Chemische Berichte, 1937, vol. 70, p. 1333,1339
[2] Chemische Berichte, 1950, vol. 83, p. 420,425,430
[3] Chemische Berichte, 1922, vol. 55, p. 1069
48
[ 186581-53-3 ]
[ 60-29-7 ]
[ 56-40-6 ]
[ 107-43-7 ]
Reference：
[1] Chemische Berichte, 1922, vol. 55, p. 1069
Glycine (lg, 13.3 mmol) was dissolved in isopropanol (10 mL) at 0°C. SOCl2 (1.93 mL, 26.6 mmol) was added dropwise. The mixture was stirred at reflux overnight. After cooling, the solvent was evaporated under reduced pressure and hexane was added at 0°C. The suspension was filtered to afford the product (1.76 g, 86percent) as a white solid. NMR (300 MHz, MeOD) δ 5.13 (hept, J = 6.3 Hz, 1H, (CH3)2CHO), 3.81 (s, 2H, CH2), 1.32 (s, 3H, (CH3 2CHO . 1.30 (s, 3H, iCH3}2CHO). 13C NMR (75 MHz, MeOD) δ 168.0 (C), 71.7 ((CH3)2CHO), 41.2 (CH2), 21.9 ((CH3 2CHO . HRMS [M+H]+ C5H12NO2: Calcd. 1 18.0858 found 1 18.0863.
Reference：
[1] RSC Advances, 2017, vol. 7, # 17, p. 10158 - 10174
[2] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 12, p. 1197 - 1201
[3] Patent: WO2015/1024, 2015, A1, . Location in patent: Page/Page column 93
[4] European Journal of Organic Chemistry, 2001, # 10, p. 1971 - 1982
[5] ChemSusChem, 2011, vol. 4, # 5, p. 604 - 608
[6] Patent: CN103242187, 2016, B, . Location in patent: Paragraph 0046
[7] Food Chemistry, 2018, vol. 268, p. 220 - 232
51
[ 83-44-3 ]
[ 56-40-6 ]
[ 16409-34-0 ]
Reference：
[1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 20, p. 4109 - 4115
With sodium hydroxide; In 1,4-dioxane; water; at 4℃; for 20.75h;
4.1 N-(4-Methoxybenzoyl)glycine 2.93 g (39 mmol) of glycine dissolved in 41 ml of aqueous 1N sodium hydroxide solution are placed in a 250 ml round-bottomed flask, the mixture is cooled to 4° C., 41 ml of aqueous 1N sodium hydroxide solution and a solution of 7 g (0.041 mol) of 4-methoxybenzoyl chloride in 10 ml of dioxane are added simultaneously, dropwise over 45 minutes, and the mixture is stirred for 20 hours. Concentrated aqueous hydrochloric acid solution is added to pH 1 and the precipitate formed is collected by filtration and recrystallized from isopropyl alcohol. 3.74 g of product are obtained. Melting point: 173° C.
With sodium hydroxide; for 0.5h;
General procedure: Glycine (5.0 g, 66.7 mmol) was dissolved in 50 mL of 10percent NaOH solution. BzCl (10.79 mL, 93.0 mmol) was added to the solution and stirred vigorously for 30 min. Crushed ice (60 g) was added to the solution and then concentrated HCl was added dropwise until the mixture was acidified (pH 2-3). The precipitate was filtrated and washed with distilled water until neutrality. The product 2-benzamidoacetic acid was obtained after drying in vacuum.
With sodium hydroxide;
General procedure: Glycine (133.0 mmol) wasdissolved in 10percent sodium hydroxide solution (100mL),and then benzoyl chloride (186.0 mmol) was added in portions tothis solution, stirred vigorously after each addition. Crushedice (100 g)was added to the solution and then concentrated HClwas added dropwise until the mixture was acidified (pH2-3). The resulting compounds1a-1g were obtained as whitecrystalline solid. All spectroscopic data of 1a-g[1-3]are in good agreement with the literature reported data
With sodium hydroxide; at 20℃; for 4h;
Add 10 mL of 10percent NaOH solution to a 50 mL three-necked flask, add 0.75 g of glycine to dissolve, slowly add 1.71 g of 4-methoxybenzoyl chloride dropwise, stir at room temperature for 4 h, adjust the pH to 1-2 with hydrochloric acid, and precipitate a white solid. Tetrahydrofuran: Toluene = 2:1 recrystallization purification to carry out the next condensation reaction.1.0 mmol of the compound VII, 1.0 mmol of the prepared carboxylic acid in 20 mL of CH 2 Cl 2 , the temperature was controlled at about 0 ° C, and 1.2 mmol of EDCI, 2.0 mmol of DIPEA, 1.2 mmol of HOBt were added in sequence, and the reaction was stirred at room temperature overnight. After washing with 10 mL of a 5percent HCl solution, 10 mL of a 5percent NaHCO 3 solution, and 10 mL of a saturated brine, the mixture was dried over anhydrous Na 2 SO 4 and then evaporated to dryness. White solid, yield 58percent
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;
1442(g): To a solution of Compound 1442(f) (70 mg, 0.15 mmol) and <strong>[22356-89-4]glycine N-methyl amide</strong> (29 mg, 0.25 mmol) in DMF was added diisopropylethylamine (0.06 mL, 0.37 mmol) and HBTU (85 mg, 0.25 mmol). After stirring overnight, the solid product was filtered from the solution to give the coupled glycine (60 mg, 75percent) as a white solid: ES-MS (M+H)+532.4.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
Life Science
For Research Only
88K+ Compounds
Competitive Price
1-2 Day Shipping
