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[ CAS No. 2488-15-5 ]

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Chemical Structure| 2488-15-5
Chemical Structure| 2488-15-5
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CAS No. :2488-15-5 MDL No. :MFCD00065586
Formula : C10H19NO4S Boiling Point : 415.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :249.33 g/mol Pubchem ID :89857
Synonyms :

Safety of [ 2488-15-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2488-15-5 ]

  • Upstream synthesis route of [ 2488-15-5 ]
  • Downstream synthetic route of [ 2488-15-5 ]

[ 2488-15-5 ] Synthesis Path-Upstream   1~27

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  • [ 2488-15-5 ]
  • [ 14486-03-4 ]
Reference: [1] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1984, p. 2305 - 2308
  • 2
  • [ 63-68-3 ]
  • [ 24424-99-5 ]
  • [ 2488-15-5 ]
YieldReaction ConditionsOperation in experiment
95% With triethylamine; sodium hydroxide In water; acetonitrile at 0 - 25℃; for 12 h; Example 1[0040][0041] 7.2 g Methionine was dissolved in a mixture of 50 mL water and 50 mL acetonitrile. To this solution was added2 g NaOH (0.05 mol). The obtained mixture was cooled down to 0°C and then 10.9 g di-t-butyl dicarbonate (0.05 mol)was added. After addition, the mixture was warmed to room temperature (24-25°C) and reacted for 12 h. Acetonitrilewas removed by distillation. Potassium carbonate was added to the residue and the pH thereof was adjusted to 12. Afterextracted with 50 mL dichloromethane twice, the organic layers were discarded. To the aqueous layer was added 1 Ndilute hydrochloric acid to adjust the pH to 6. After extracted with 50 mL dichloromethane twice, the organic layers werecollected together and washed with 50 mL saturate solution of sodium chloride and then dried over anhydrous sodiumsulfate, followed by concentration to obtain a viscous product (11.4 g). The yield was 95percent.1H NMR (500 MHz, CDCl3) δ 11.62 (br, 1 H), 6.91 (br, 1 H), 4.40 (m. 1H), 2.52 (t, J = 4.8 Hz, 2 H), 2.05 (s, 3H), 1.92∼2.15(m. 2 H), 1.42 (s, 9 H). Ms (M++1): 250.
60% With sodium hydroxide In water; acetonitrile at 0 - 20℃; for 12 h; To the solution of L-methionine (43) (2 g, 13.40 mmol) in water (12 mL) and acetonitrile (12 mL) was added NaOH (0.804 g, 20.11 mmol) and boc-anhydride (4.67 mL, 20.11 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 12h. After completion, reaction mixture was concentrated under vacuum to remove acetonitrile and the remaining acqueous layer was diluted with 50 mL water. Aqueous layer was washed with ethylacetate (2 x 50 mL). The aqueous phase was then adjusted to pH ~ 4-5 using aqueous 1N HCl solution and extracted with dichloromethane (4 x 50 mL). Combined organic extracts were washed with brine (100 mL), dried over Sodium sulphate and evaporated under reduced pressure to yield (tert-butoxycarbonyl)-L-methionine (44) as a gummy compound (0.6 g, 8.02 mmol, 60 percent yield) 1H NMR (400 MHz, DMSO-d6): δ 12.47 (br-s, 1H), 7.10 (d, J = 8.0 Hz, 1H), 4.00 (dd, J = 8.3, 4.3 Hz, 1H), 2.60-2.45 (m, 2H), 2.03 (s, 3H), 1.94-1.75 (m, 2H), 1.38 (s, 9H) MS (ESI): 248.2 as [M-1] in -Ve mode.
Reference: [1] Antimicrobial Agents and Chemotherapy, 2017, vol. 61, # 3,
[2] Tetrahedron Letters, 1994, vol. 35, # 14, p. 2121 - 2124
[3] Patent: EP2647624, 2013, A1, . Location in patent: Paragraph 0040; 0041
[4] Organic Syntheses, 1985, vol. 63, p. 160 - 160
[5] Tetrahedron Letters, 2018, p. 4267 - 4271
[6] Chemistry of Natural Compounds, 1979, vol. 15, p. 471 - 476[7] Khimiya Prirodnykh Soedinenii, 1979, vol. 15, p. 543 - 548
[8] Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 4, p. 242 - 249
[9] Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 4, p. 250 - 256
[10] Journal of the Chemical Society - Series Chemical Communications, 1989, # 22, p. 1740 - 1742
[11] Journal of Medicinal Chemistry, 2003, vol. 46, # 16, p. 3502 - 3507
[12] Bioorganic and medicinal chemistry letters, 2004, vol. 14, # 1, p. 275 - 278
[13] Organic letters, 2002, vol. 4, # 23, p. 4005 - 4008
[14] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 23, p. 9984 - 9990
[15] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 2, p. 887 - 895
[16] Journal of Enzyme Inhibition and Medicinal Chemistry, 2011, vol. 26, # 4, p. 506 - 513
[17] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2012, vol. 67, # 7, p. 731 - 746
[18] Molecules, 2014, vol. 19, # 10, p. 16349 - 16372
[19] Chemistry - A European Journal, 2015, vol. 21, # 51, p. 18589 - 18593
[20] Molecules, 2016, vol. 21, # 2,
[21] Organic and Biomolecular Chemistry, 2017, vol. 15, # 40, p. 8493 - 8498
[22] Chemistry - An Asian Journal, 2018, vol. 13, # 4, p. 400 - 403
  • 3
  • [ 63-68-3 ]
  • [ 34619-03-9 ]
  • [ 2488-15-5 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With sodium hydroxide In water; acetonitrile at 0 - 45℃; for 12 h;
Stage #2: With hydrogenchloride In water
7.2 g Methionine was dissolved in a mixture of 50 mL water and 50 mL acetonitrile. To this solution was added 2 g NaOH (0.05 mol). The obtained mixture was cooled down to 0° C. and then 10.9 g di-t-butyl dicarbonate (0.05 mol) was added. After addition, the mixture was warmed to room temperature (24-25° C.) and reacted for 12 h. Acetonitrile was removed by distillation. Potassium carbonate was added to the residue and the pH thereof was adjusted to 12. After extracted with 50 mL dichloromethane twice, the organic layers were discarded. To the aqueous layer was added 1N dilute hydrochloric acid to adjust the pH to 6. After extracted with 50 mL dichloromethane twice, the organic layers were collected together and washed with 50 mL saturate solution of sodium chloride and then dried over anhydrous sodium sulfate, followed by concentration to obtain a viscous product (11.4 g). The yield was 95percent. 1H NMR (500 MHz, CDCl3) δ 11.62 (br, 1H), 6.91 (br, 1H), 4.40 (m. 1H), 2.52 (t, J=4.8 Hz, 2H), 2.05 (s, 3H), 1.922.15 (m. 2H), 1.42 (s, 9H). Ms (M++1): 250.
Reference: [1] Patent: US2013/281695, 2013, A1, . Location in patent: Paragraph 0082-0084
  • 4
  • [ 63-68-3 ]
  • [ 98015-52-2 ]
  • [ 2488-15-5 ]
Reference: [1] Synthesis, 1986, # 8, p. 627 - 632
  • 5
  • [ 63-68-3 ]
  • [ 2488-15-5 ]
Reference: [1] Chemistry Letters, 1984, p. 237 - 238
[2] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1984, p. 2305 - 2308
  • 6
  • [ 63-68-3 ]
  • [ 130384-98-4 ]
  • [ 2488-15-5 ]
Reference: [1] Synlett, 2011, # 14, p. 2013 - 2016
  • 7
  • [ 24424-99-5 ]
  • [ 71989-28-1 ]
  • [ 2488-15-5 ]
Reference: [1] Tetrahedron Letters, 1993, vol. 34, # 9, p. 1413 - 1414
  • 8
  • [ 89985-91-1 ]
  • [ 142-08-5 ]
  • [ 2488-15-5 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 12, p. 3570 - 3575
  • 9
  • [ 105678-24-8 ]
  • [ 2637-34-5 ]
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Reference: [1] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 12, p. 3570 - 3575
  • 10
  • [ 63-68-3 ]
  • [ 75844-68-7 ]
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1984, vol. 32, # 6, p. 2174 - 2181
  • 11
  • [ 1070-19-5 ]
  • [ 63-68-3 ]
  • [ 2488-15-5 ]
Reference: [1] Helvetica Chimica Acta, 1959, vol. 42, p. 2622
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1977, vol. 15, p. 80 - 81
[3] Journal of Organic Chemistry, 1971, vol. 36, p. 3022 - 3026
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  • [ 63-68-3 ]
  • [ 50739-44-1 ]
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Reference: [1] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 10, p. 2974 - 2980
  • 13
  • [ 71989-28-1 ]
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Reference: [1] Tetrahedron Letters, 1993, vol. 34, # 9, p. 1413 - 1414
  • 14
  • [ 22823-50-3 ]
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Reference: [1] Pharmaceutical Chemistry Journal, 1981, vol. 15, # 10, p. 720 - 725[2] Khimiko-Farmatsevticheskii Zhurnal, 1981, vol. 15, # 10, p. 37 - 42
  • 15
  • [ 24424-99-5 ]
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Reference: [1] Synlett, 2011, # 14, p. 2013 - 2016
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  • [ 63-68-3 ]
  • [ 4981-48-0 ]
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Reference: [1] Journal of the American Chemical Society, 1965, vol. 87, p. 631 - 639
  • 17
  • [ 63-68-3 ]
  • [ 18595-34-1 ]
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Reference: [1] Justus Liebigs Annalen der Chemie, 1968, vol. 716, p. 175 - 185
  • 18
  • [ 63-68-3 ]
  • [ 16965-08-5 ]
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Reference: [1] Journal of the Chemical Society [Section] C: Organic, 1967, p. 2632 - 2636
  • 19
  • [ 2488-18-8 ]
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Reference: [1] Russian Journal of Organic Chemistry, 2007, vol. 43, # 4, p. 548 - 552
  • 20
  • [ 63-68-3 ]
  • [ 24608-52-4 ]
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Reference: [1] Zeitschrift fuer Chemie (Stuttgart, Germany), 1973, vol. 13, p. 221 - 222
  • 21
  • [ 75-44-5 ]
  • [ 63-68-3 ]
  • [ 1907-33-1 ]
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Reference: [1] Chemische Berichte, 1985, vol. 118, # 2, p. 468 - 482
  • 22
  • [ 2488-15-5 ]
  • [ 51372-93-1 ]
YieldReaction ConditionsOperation in experiment
85% With sodium tetrahydroborate; iodine In tetrahydrofuran; methanol at 0 - 5℃; for 2 h; Reflux [0060] Into a 500 mL three-necked flask were added the starting compound as shown in the above route (49.8 g, 0.5mol) and 250 mL tetrahydrofuran. The temperature of the reaction mixture was adjusted to about 0-5°C in an ice-saltbath with agitation. To this mixture, sodium borohydride (19 g, 0.5 mol) was added slowly, followed by the addition of50 mL methanol. After addition, 100 mL solution of iodine (127 g, 0.5 mol) in tetrahydrofuran was added. Then, thereaction system was warmed to reflux. The reaction was continued for 2 h under agitation. After the raw material wasconsumed under the detecting of TLC, the temperature of the reaction mixture was adjusted with an ice-water bath.Saturated solution of ammonia chloride was added to quench the reaction. After 100 mL THF was evaporated out by arotary evaporator under reduced pressure, the residue was extracted with ethyl acetate (300 mL32).·The obtainedorganic layer was washed with dilute hydrochloric acid, followed by saturated sodium hydrogen carbonate, and finallyaqueous solution of sodium chloride. After drying and concentrating, a crude product (120 g) was obtained as an oil.The crude product was further treated by column chromatography to obtain a purified product (97.5 g). The yield was 85percent.1H NMR (400 MHz, CDCl3) δ 11.64(br, 1 H), 6.85 (br, 1 H), 4.55∼4.48 (m, 1 H), 2.53 (t, J = 4.9 Hz, 2H), 3.44 (s, 3H),2.05 (s, 3H), 2.02∼1.87 (m, 2H), 1.48 (s, 9H). Ms (M++1): 236.
85% With methanol; sodium tetrahydroborate; iodine In tetrahydrofuran at 0 - 5℃; for 2 h; Reflux Into a 500 mL three-necked flask were added the starting compound as shown in the above route (49.8 g, 0.5 mol) and 250 mL tetrahydrofuran. The temperature of the reaction mixture was adjusted to about 0-5° C. in an ice-salt bath with agitation. To this mixture, sodium borohydride (19 g, 0.5 mol) was added slowly, followed by the addition of 50 mL methanol. After addition, 100 mL solution of iodine (127 g, 0.5 mol) in tetrahydrofuran was added. Then, the reaction system was warmed to reflux. The reaction was continued for 2 h under agitation. After the raw material was consumed under the detecting of TLC, the temperature of the reaction mixture was adjusted with an ice-water bath. Saturated solution of ammonia chloride was added to quench the reaction. After 100 mL THF was evaporated out by a rotary evaporator under reduced pressure, the residue was extracted with ethyl acetate (300 mL×2). The obtained organic layer was washed with dilute hydrochloric acid, followed by saturated sodium hydrogen carbonate, and finally aqueous solution of sodium chloride. After drying and concentrating, a crude product (120 g) was obtained as an oil. The crude product was further treated by column chromatography to obtain a purified product (97.5 g). The yield was 85percent. 1H NMR (400 MHz, CDCl3) δ 11.64 (br, 1H), 6.85 (br, 1H), 4.554.48 (m, 1H), 2.53 (t, J=4.9 Hz, 2H), 3.44 (s, 3H), 2.05 (s, 3H), 2.021.87 (m, 2H), 1.48 (s, 9H). Ms (M++1): 236.
Reference: [1] Antimicrobial Agents and Chemotherapy, 2017, vol. 61, # 3,
[2] Patent: EP2647624, 2013, A1, . Location in patent: Paragraph 0059; 0060
[3] Patent: US2013/281695, 2013, A1, . Location in patent: Paragraph 0108-0110
[4] Organic Letters, 2005, vol. 7, # 5, p. 847 - 849
[5] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 5, p. 1921 - 1924
[6] Synthesis, 1990, p. 299 - 301
[7] Journal of Medicinal Chemistry, 2014, vol. 57, # 13, p. 5748 - 5763
[8] Antimicrobial Agents and Chemotherapy, 2018, vol. 62, # 12,
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Reference: [1] Chemische Berichte, 1980, vol. 113, # 11, p. 3511 - 3516
[2] Journal of Organic Chemistry, 1991, vol. 56, # 19, p. 5606 - 5610
[3] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1984, p. 2305 - 2308
[4] European Journal of Pharmacology, 2001, vol. 411, # 3, p. 327 - 333
[5] Journal of Medicinal Chemistry, 2003, vol. 46, # 21, p. 4543 - 4551
[6] Journal of the American Chemical Society, 2001, vol. 123, # 6, p. 1023 - 1035
[7] Organic Letters, 2007, vol. 9, # 22, p. 4423 - 4426
[8] Chemistry Letters, 2013, vol. 42, # 6, p. 601 - 603
  • 24
  • [ 74124-79-1 ]
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  • [ 3845-64-5 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 9, p. 4008 - 4017
  • 25
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  • [ 91103-37-6 ]
Reference: [1] Organic Letters, 2005, vol. 7, # 5, p. 847 - 849
  • 26
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  • [ 91103-37-6 ]
Reference: [1] Tetrahedron Letters, 1984, vol. 25, # 10, p. 1071 - 1074
  • 27
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  • [ 89985-86-4 ]
Reference: [1] Tetrahedron Letters, 1984, vol. 25, # 10, p. 1071 - 1074
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