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[ CAS No. 20277-69-4 ]

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Chemical Structure| 20277-69-4
Chemical Structure| 20277-69-4
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CAS No. :20277-69-4 MDL No. :MFCD00040392
Formula : CH3NaO2S Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :102.09 g/mol Pubchem ID :-
Synonyms :

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Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P301+P312-P330-P501 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
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Application In Synthesis of [ 20277-69-4 ]

  • Upstream synthesis route of [ 20277-69-4 ]
  • Downstream synthetic route of [ 20277-69-4 ]

[ 20277-69-4 ] Synthesis Path-Upstream   1~24

  • 1
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  • [ 78-95-5 ]
  • [ 5000-46-4 ]
Reference: [1] Heterocycles, 2007, vol. 73, # C, p. 469 - 480
[2] Patent: WO2012/33225, 2012, A1, . Location in patent: Page/Page column 250-251
  • 2
  • [ 20277-69-4 ]
  • [ 598-31-2 ]
  • [ 5000-46-4 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 23, p. 3853 - 3856
  • 3
  • [ 20277-69-4 ]
  • [ 105-36-2 ]
  • [ 4455-15-6 ]
YieldReaction ConditionsOperation in experiment
85% at 20℃; for 12 h; To a solution of ethyl 2-bromoacetate (330 g, 1.98 mol) in DMF (1500 mL) was added MeSO2Na (240 g, 2.35 mol). The mixture was stirred at room temprature for 24 hours. Then water was added, and the resulted mixture was extracted with ethyl acetate. The separated organic layer was washed with brine, dried over Na2SO4 , and concentrated in vacuo to give ethyl 2-methylsulfonylacetate (280 g, 85percent); 1H NMR (400 MHz, CDCI3) δ 4.20 (2H, q), 3.95 (2H, s), 3.13 (3H, s), 1.23-1.25 (3H).
Reference: [1] Patent: WO2010/136778, 2010, A1, . Location in patent: Page/Page column 60-61
  • 4
  • [ 106-41-2 ]
  • [ 20277-69-4 ]
  • [ 14763-60-1 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 12, p. 6589 - 6599
[2] Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2696 - 2700
  • 5
  • [ 71597-85-8 ]
  • [ 20277-69-4 ]
  • [ 14763-60-1 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 17, p. 3405 - 3408
  • 6
  • [ 540-38-5 ]
  • [ 20277-69-4 ]
  • [ 14763-60-1 ]
Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2696 - 2700
  • 7
  • [ 20277-69-4 ]
  • [ 627-18-9 ]
  • [ 2058-49-3 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 5, p. 441 - 445
  • 8
  • [ 1073-06-9 ]
  • [ 20277-69-4 ]
  • [ 657-46-5 ]
Reference: [1] Patent: US2010/273816, 2010, A1, . Location in patent: Page/Page column 41
  • 9
  • [ 95-73-8 ]
  • [ 20277-69-4 ]
  • [ 1671-18-7 ]
Reference: [1] Chinese Journal of Chemistry, 2017, vol. 35, # 11, p. 1661 - 1664
  • 10
  • [ 20277-69-4 ]
  • [ 591-19-5 ]
  • [ 35216-39-8 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 12, p. 6589 - 6599
  • 11
  • [ 20277-69-4 ]
  • [ 3433-80-5 ]
  • [ 25195-52-2 ]
YieldReaction ConditionsOperation in experiment
94% at 60℃; for 1 h; Intermediate 4: 1-Bromo-2-((methylsulfonyl)methyl)benzene2- Bromobenzylbromide (250 mg, 1 .00 mmol), sodium methanesulfinate (303 mg, 2.97 mmol) and DMF (2.5 mL) was added to a 10 mL cone shaped flask and stirred at 60°C for 1 hour. The reaction was cooled to room temperature, added water and extracted with EtOAc (x3). The organic phases were combined, washed with water (x2), brine (x1), dried over MgS04 and concentrated under vacuum to give 235 mg (94percent) of a white solid: Rf = 0.34 (EtOAc: petroleum ether, 1 :2); 1 H NMR (CDCI3) δ 7.67 - 7.63 (m, 1 H), 7.61 (dd, J = 7.7 Hz, 1 .5 Hz, 1 H), 7.40 (td, J = 7.6 Hz, 0.9 Hz, 1 H), 7.27 (td, J = 7.8 Hz, 1.6 Hz, 1 H), 4.52 (s, 2H), 2.82 (s, 3H); 13C NMR (CDCI3) δ 133.4, 133.1 , 130.8, 128.5, 128.3, 125.0, 60.4, 39.9; ESI-MS m/z 270.9 (M+Na+).
Reference: [1] Patent: WO2012/136221, 2012, A1, . Location in patent: Page/Page column 41
[2] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 5, p. 441 - 445
  • 12
  • [ 20277-69-4 ]
  • [ 96-34-4 ]
  • [ 62020-09-1 ]
Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 8, p. 1486 - 1489
  • 13
  • [ 124-63-0 ]
  • [ 20277-69-4 ]
Reference: [1] Journal of the American Chemical Society, 1981, vol. 103, # 5, p. 1137 - 1145
[2] Helvetica Chimica Acta, 2003, vol. 86, # 1, p. 65 - 81
[3] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 187 - 190
[4] Journal of Pharmacology and Experimental Therapeutics, 1997, vol. 281, # 2, p. 611 - 617
[5] Patent: WO2012/33225, 2012, A1, . Location in patent: Page/Page column 250-251
[6] Molecules, 2013, vol. 18, # 1, p. 97 - 113
[7] Russian Journal of Organic Chemistry, 2016, vol. 52, # 6, p. 862 - 872[8] Zh. Org. Khim., 2016, vol. 52, # 6, p. 862 - 872,11
[9] Organic Letters, 2016, vol. 18, # 16, p. 4144 - 4147
[10] Organic Letters, 2018, vol. 20, # 17, p. 5353 - 5356
[11] Chemical Communications, 2017, vol. 53, # 12, p. 2056 - 2059
[12] European Journal of Medicinal Chemistry, 2018, vol. 160, p. 120 - 132
  • 14
  • [ 676-85-7 ]
  • [ 20277-69-4 ]
Reference: [1] European Journal of Organic Chemistry, 2017, vol. 2017, # 5, p. 1025 - 1032
  • 15
  • [ 50-00-0 ]
  • [ 20277-69-4 ]
Reference: [1] Patent: EP1561747, 2005, A2, . Location in patent: Page/Page column 4
  • 16
  • [ 7144-49-2 ]
  • [ 95-16-9 ]
  • [ 20277-69-4 ]
Reference: [1] Chemistry Letters, 1984, p. 2125 - 2128
  • 17
  • [ 96088-55-0 ]
  • [ 20277-69-4 ]
  • [ 7632-00-0 ]
Reference: [1] Chemische Berichte, 1987, vol. 120, p. 351 - 354
  • 18
  • [ 77-79-2 ]
  • [ 623-11-0 ]
  • [ 20277-69-4 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 1677
  • 19
  • [ 1192-16-1 ]
  • [ 623-11-0 ]
  • [ 20277-69-4 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 1677
  • 20
  • [ 20277-69-4 ]
  • [ 34557-54-5 ]
  • [ 74-84-0 ]
  • [ 2386-57-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2, 2001, # 5, p. 787 - 792
  • 21
  • [ 20277-69-4 ]
  • [ 1950-85-2 ]
YieldReaction ConditionsOperation in experiment
77% With sulfur In methanol for 0.333333 h; Heating / reflux A mixture of sodium methanesulfinate (5.43 g, 53 mmol) and sulphur (1.666 g, 52 mmol) in dry methanol (310 ml) was heated to reflux for 20 min, at which time almost all of the sulphur had dissolved. The hot solution was filtered and the filtrate concentrated to dryness. The off-white solid was stirred with a small amount of dry ethanol 0 at room temperature, filtered and concentrated. The trituration was repeated until 1H NMR of the white residue showed no more traces of sodium methanethiosulfonate. The filtrates were then combined and evaporated to dryness to yield the title compound (5.40 g, 77percent) as fine EPO <DP n="41"/>white needles; mp 271-2720C (lit.[G.L. Kenyon, T. W. Bruice, Methods Enzymol. 1977, 47, 407-430.] 272-273.50C); 1H NMR (200 MHz, CDCl3) δ 3.18 (s, 3H, CH3); anal, calculated, for CH3NaO2S2: C 8.95, H 2.25; found: C 8.86, H 2.55.; Improved Synthesis for NaMTS EPO <DP n="40"/>[0136] An alternative preparation of NaMTS (J.D. Macke, L. Field, /. Org. Chem. 1988, 53, 396-402) has been successfully tested, which is faster and avoids the tedious and lengthy separation of by-product from NaMTS as required in the Na2SZMe3SiCl method. NaMTS was synthesized in high yield by refluxing sodium sulfinate with sulphur in methanol s (Scheme 16, Fig. 19), described in further detail below). Although formation of small amounts of an unknown by-product was observed, it could be easily separated from NaMTS.
Reference: [1] Chemistry Letters, 1987, p. 2161 - 2162
[2] Patent: WO2006/55437, 2006, A2, . Location in patent: Page/Page column 38; 39; sheet 23
[3] Journal of Organic Chemistry, 2005, vol. 70, # 24, p. 9740 - 9754
[4] Dalton Transactions, 2011, vol. 40, # 45, p. 12310 - 12319
[5] Journal of Organic Chemistry, 1988, vol. 53, # 2, p. 396 - 402
  • 22
  • [ 20277-69-4 ]
  • [ 13223-25-1 ]
  • [ 113583-35-0 ]
Reference: [1] Tetrahedron, 2000, vol. 56, # 27, p. 4739 - 4745
  • 23
  • [ 20277-69-4 ]
  • [ 90176-80-0 ]
  • [ 1215310-75-0 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 5, p. 582 - 586
[2] Drugs of the Future, 2018, vol. 43, # 8, p. 565 - 572
  • 24
  • [ 20277-69-4 ]
  • [ 67567-26-4 ]
  • [ 1147557-74-1 ]
Reference: [1] Patent: WO2009/55331, 2009, A2, . Location in patent: Page/Page column 199
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