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[ CAS No. 2491-18-1 ]

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Chemical Structure| 2491-18-1
Chemical Structure| 2491-18-1
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CAS No. :2491-18-1 MDL No. :MFCD00012491
Formula : C6H14ClNO2S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :199.70 g/mol Pubchem ID :11435579
Synonyms :

Safety of [ 2491-18-1 ]

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:

Application In Synthesis of [ 2491-18-1 ]

  • Upstream synthesis route of [ 2491-18-1 ]
  • Downstream synthetic route of [ 2491-18-1 ]

[ 2491-18-1 ] Synthesis Path-Upstream   1~6

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  • [ 108-24-7 ]
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YieldReaction ConditionsOperation in experiment
94% at 20℃; Cooling with ice In a typical reaction, 73 mL of acetic anhydride (780 mmol) and 63 mL pyridine (780 mmol) were combined in a round-bottomed flask and chilled on ice. After 5-10 min, 8.6 g (100 mmol) l-methionine methyl ester HCl were added and the reaction mixture was allowed to slowly return to room temperature overnight. The next morning, the reaction was quenched with cold water and extracted four times with 75 mL of methylene chloride. The extracts were then rinsed three times each with 1 M HCl, saturated sodium bicarbonate solution, and water. The extracts were then dried over MgSO4, filtered, and evaporated under reduced pressure, yielding a yellow oil which crystallized upon standing. The crude product was recrystallized in ethyl ether at -20 °C. Crystals (19.3 g, 94 mmol, 94percent) were isolated by vacuum filtration. Mp = 41.7-42.4 °C. 1H NMR ([2H]-chloroform, TMS = 0.0 ppm): δ 1.86-2.20 (m, 2H), δ 2.00 (s, 3H), δ 2.05 (s, 3H), δ 2.45-2.60 (m, 2H), δ 3.75 (s, 3H), δ 4.62-4.70 (m, 1H), δ 6.13-6.19 (bd, 1H).
Reference: [1] Tetrahedron Asymmetry, 2011, vol. 22, # 3, p. 283 - 293
[2] Chemical and pharmaceutical bulletin, 1986, vol. 34, # 3, p. 986 - 998
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  • [ 2491-18-1 ]
  • [ 501-53-1 ]
  • [ 56762-93-7 ]
Reference: [1] Synthetic Communications, 1989, vol. 19, # 20, p. 3457 - 3468
[2] European Journal of Organic Chemistry, 2008, # 18, p. 3107 - 3112
[3] Organic Syntheses, 1992, vol. 70, p. 29 - 29
[4] Journal of Organic Chemistry, 1980, vol. 45, # 24, p. 4817 - 4820
[5] Tetrahedron Letters, 2010, vol. 51, # 24, p. 3226 - 3228
  • 3
  • [ 13139-17-8 ]
  • [ 2491-18-1 ]
  • [ 56762-93-7 ]
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 16, p. 3507 - 3518
  • 4
  • [ 67-56-1 ]
  • [ 63-68-3 ]
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YieldReaction ConditionsOperation in experiment
98% at 0℃; for 16 h; Inert atmosphere; Reflux Synthesis Example 1 \\ ,L-Methionine (0.5g, 1 equivalent) was suspended in methanol (30ml C = 0.1M) in a 100ml flask equipped with a magnetic stirrer and placed under nitrogen. Thionyl chloride (0.5ml, 2 equivalents) was added to the solution dropwise at 0°C then heated under reflux for 16 hours. The reaction mixture was then evaporated to yield a pale yellow solid. The solid was triturated with hot diethyl ether and the solution discarded to leave the title compound 2 as a white solid which was further dried under vacuum. (0.65561 g, 98percent yield).1H NMR (D20, 500MHz) δΗ: 4.24(1 H, m, 3) 3.79(3H, s, 1), 2.63(2H, t, 5), 2.25(1 H, m, 4), 2.16(1H, m, 4), 2.06(1H, s, 6)13C NMR( D20, 125MHz) 6C: 170.58 (2), 53.64(1), 51.70(3), 28.71(4), 28.41(5), 13.85(6).IR (neat, vmax, cnV1): 2880.8/2676,2 (CH3, CH2, CH), 2016.2, 1742.2 (C=0, ester), 1483.6, 1443.5, 1227 + 1194.7 + 1149.8 + 1079.5 (C-O).HRMS m/z (+ESI): C6Hi4N02S, mass found = 64.074 (Error = 0.07ppm)
98% at 0℃; for 16 h; Inert atmosphere; Reflux L-Methionine (0.5 g, 1 equivalent) was suspended in methanol (30 ml C=0.1M) in a 100 ml flask equipped with a magnetic stirrer and placed under nitrogen. Thionyl chloride (0.5 ml, 2 equivalents) was added to the solution dropwise at 0° C. then heated under reflux for 16 hours. The reaction mixture was then evaporated to yield a pale yellow solid. The solid was triturated with hot diethyl ether and the solution discarded to leave the title compound 2′ a white solid which was further dried under vacuum. (0.65561 g, 98percent yield). [0377] 1H NMR (D2O, 500 MHz) δH: 4.24 (1H, m, 3) 3.79 (3H, s, 1), 2.63 (2H, t, 5), 2.25 (1H, m, 4), 2.16 (1H, m, 4), 2.06 (1H, s, 6) [0378] 13C NMR (D2O, 125 MHz) δc: 170.58 (2), 53.64 (1), 51.70 (3), 28.71 (4), 28.41 (5), 13.85 (6). [0379] IR (neat, vmax, cm−1): 2880.8/2676.2 (CH3, CH2, CH), 2016.2, 1742.2 (C═O, ester), 1483.6, 1443.5, 1227+1194.7+1149.8+1079.5 (C—O). [0380] HRMS m/z (+ESI): C6H14NO2S, mass found=164.074 (Error=0.071 ppm)
89% at 20℃; for 24 h; Inert atmosphere; Reflux Using the general methyl esterification conditions, L-methionine (8, 2.00 g, 13.4 mmol) was treated with thionyl chloride (2.00 mL, 26.8 mmol) in methanol(20 mL) to afford the title compound as a white powder (1.95 g, 89percent); νmax (KBr pellet): 3080 (s), 1747(s), 2840 (w), 1236 (s); δH (300 MHz, CDCl3): 2.28 (3H, s), 2.28–2.33 (2H, m), 2.67–2.77 (2H, m), 3.87(3H, s), 4.16–4.30 (1H, m); δC (75.4 MHz, CD3OD): 15.4, 30.5, 31.1, 53.2, 54.2, 171.2; m/z (ES+): 164 (100percent, [M+H]+). Data in agreement with literature [62].
67% at 20℃; Cooling with ice General procedure: This compound has previously been described5 and can be purchased from Toronto Research. To a round bottom flask containing MeOH (50 mL) and cooled in an ice bath was added SOCl2 (6.1 mL, 84 mmol) dropwise over 5 min. L-Leucine 1e (5.0 g, 38) was then added and the mixture was left to stir overnight at rt. The reaction mixture was concentrated on the rotovap using MeOH (2 x 50 mL) to chase away excess thionyl chloride. Diethyl ether (50 mL) was added to the resulting solids and followed by a combination of scratching and sonication to produce a white solid which was filtered, rinsing with diethyl ether (3 x 10 mL). Product was further purified by recrystallization by partially dissolving solids in hot EtOAc (50 mL) followed by cooling to rt and filtration. Yield: 3.9 g (56percent). [α]D24 +18.8° (c 0.50, MeOH). >98percent pure by NMR. 1H NMR ((CD3)2SO) δ 8.61 (br s, 3H), 3.95 (t, J = 7, 1H), 3.74 (s, 3H), 1.75 (m, 1H), 1.65 (m, 2H), 0.89 (d, J = 7, 6H).

Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 1, p. 201 - 215
[2] Journal of the American Chemical Society, 2017, vol. 139, # 40, p. 14077 - 14089
[3] Patent: WO2012/131313, 2012, A1, . Location in patent: Page/Page column 49
[4] Patent: US2014/39200, 2014, A1, . Location in patent: Paragraph 0376-0380
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 8, p. 1942 - 1944
[6] Organic Preparations and Procedures International, 2001, vol. 33, # 4, p. 341 - 349
[7] Synthetic Communications, 2010, vol. 40, # 8, p. 1161 - 1179
[8] Molecules, 2014, vol. 19, # 12, p. 20751 - 20767
[9] Organic Syntheses, 1992, vol. 70, p. 29 - 29
[10] Tetrahedron Letters, 2017, vol. 58, # 34, p. 3347 - 3349
[11] Archiv der Pharmazie, 2011, vol. 344, # 8, p. 494 - 504
[12] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 20, p. 5000 - 5006
[13] Synthetic Communications, 2008, vol. 38, # 5, p. 684 - 696
[14] Biomedicine and Pharmacotherapy, 2017, vol. 88, p. 1163 - 1172
[15] Journal of Biological Chemistry, 1949, vol. 180, p. 63
[16] Tetrahedron, 1990, vol. 46, # 15, p. 5325 - 5332
[17] European Journal of Medicinal Chemistry, 1985, vol. 20, # 6, p. 509 - 512
[18] Synthetic Communications, 1995, vol. 25, # 4, p. 561 - 568
[19] Journal of Medicinal Chemistry, 2006, vol. 49, # 24, p. 7215 - 7226
[20] Tetrahedron, 2004, vol. 60, # 43 SPEC. ISS., p. 9649 - 9657
[21] Journal of the American Chemical Society, 2008, vol. 130, # 15, p. 5052 - 5053
[22] European Journal of Organic Chemistry, 2008, # 14, p. 2423 - 2429
[23] Journal of Chemical Research, 2011, vol. 35, # 1, p. 47 - 50
[24] Journal of Chemical Research, 2012, vol. 36, # 4, p. 206 - 209
[25] Letters in Organic Chemistry, 2011, vol. 8, # 3, p. 210 - 215
[26] Asian Journal of Chemistry, 2012, vol. 24, # 3, p. 1227 - 1236
[27] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 12, p. 3807 - 3815
[28] Asian Journal of Chemistry, 2012, vol. 24, # 3, p. 1237 - 1241
[29] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 12, p. 1185 - 1190
[30] Polyhedron, 2018, vol. 143, p. 70 - 82
[31] Patent: CN105145577, 2018, B, . Location in patent: Paragraph 0035; 0039
[32] Amino Acids, 2018, vol. 50, # 10, p. 1461 - 1470
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Reference: [1] Journal of the American Chemical Society, 1995, vol. 117, # 11, p. 3302 - 3303
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  • [ 63-68-3 ]
  • [ 77-76-9 ]
  • [ 2491-18-1 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 24, p. 3226 - 3228
[2] Tetrahedron Asymmetry, 2008, vol. 19, # 1, p. 67 - 81
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