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Chemical Structure| 80-48-8
Chemical Structure| 80-48-8
Structure of 80-48-8 * Storage: {[proInfo.prStorage]}
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Product Citations

Tyler J. Adams ; Naz F. Tumpa ; Maithili Acharya , et al. DOI:

Abstract: Water-soluble dipyridinium thiazolo[5,4-d]thiazole (TTz) compounds are incorporated into inexpensive poly(vinyl alcohol) (PVA)/borax films and exhibit fast (<1 s), high-contrast photochromism, photofluorochromism, and oxygen sensing. Under illumination, the films change from clear/yellow TTz2+ to purple TTz•+ and then blue TTz0. The contrast and speed of the photochromism are dependent on the polymer matrix redox properties and the concentration of TTz2+. The photoreduced films exhibit strong, near-infrared light (1000–1500 nm) absorbances in addition to visible color changes. Spectroscopic ellipsometry was used to establish the complex dielectric function for the TTz2+ and TTz0 states. Incorporating non-photochromic dyes yields yellow-to-green and pink-to-purple photochromism. Additionally, when illuminated, reversible photoactuation occurs, causing mechanical contraction in the TTz-embedded films. The blue film returns to its colorless state via exposure to O2, making the films able to sense oxygen and leak direction for smart packaging. These films show potential for use in self-tinting smart windows, eyeglasses, displays, erasable memory devices, fiber optic communication, and oxygen sensing.

Keywords: photochromic ; photofluorochromic ; photoactuator ; thiazolothiazole ; oxygen sensor ; sensing ; green chemistry

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Product Details of [ 80-48-8 ]

CAS No. :80-48-8 MDL No. :MFCD00008417
Formula : C8H10O3S Boiling Point : -
Linear Structure Formula :- InChI Key :VUQUOGPMUUJORT-UHFFFAOYSA-N
M.W : 186.23 Pubchem ID :6645
Synonyms :

Calculated chemistry of [ 80-48-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.59
TPSA : 51.75 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.9
Log Po/w (XLOGP3) : 1.54
Log Po/w (WLOGP) : 2.41
Log Po/w (MLOGP) : 1.78
Log Po/w (SILICOS-IT) : 1.11
Consensus Log Po/w : 1.75

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.2
Solubility : 1.17 mg/ml ; 0.00627 mol/l
Class : Soluble
Log S (Ali) : -2.24
Solubility : 1.08 mg/ml ; 0.00581 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.84
Solubility : 0.27 mg/ml ; 0.00145 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.02

Safety of [ 80-48-8 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P272-P273-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P333+P313-P362+P364-P405-P501 UN#:3265
Hazard Statements:H302-H314-H317-H401 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 80-48-8 ]

* 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.

  • Upstream synthesis route of [ 80-48-8 ]
  • Downstream synthetic route of [ 80-48-8 ]

[ 80-48-8 ] Synthesis Path-Upstream   1~47

  • 1
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Reference: [1] New Journal of Chemistry, 2010, vol. 34, # 11, p. 2558 - 2563
  • 2
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Reference: [1] Bulletin de la Societe Chimique de France, 1967, p. 4134 - 4143
  • 3
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  • [ 15679-12-6 ]
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Reference: [1] Bulletin de la Societe Chimique de France, 1967, p. 4134 - 4143
  • 4
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  • [ 694-32-6 ]
Reference: [1] Journal of the American Chemical Society, 1958, vol. 80, p. 6409,6412
  • 5
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  • [ 408492-27-3 ]
  • [ 39621-00-6 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 49, p. 17197 - 17202
  • 6
  • [ 1849-55-4 ]
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  • [ 1849-53-2 ]
Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 481,483
  • 7
  • [ 26137-08-6 ]
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  • [ 81452-54-2 ]
Reference: [1] Chemical Communications, 2017, vol. 53, # 73, p. 10180 - 10183
  • 8
  • [ 181226-89-1 ]
  • [ 80-48-8 ]
  • [ 81452-54-2 ]
Reference: [1] Chemical Communications, 2017, vol. 53, # 73, p. 10180 - 10183
  • 9
  • [ 10075-50-0 ]
  • [ 80-48-8 ]
  • [ 10075-52-2 ]
Reference: [1] Patent: US6017945, 2000, A,
  • 10
  • [ 80-48-8 ]
  • [ 2382-96-9 ]
  • [ 74-88-4 ]
  • [ 13673-62-6 ]
Reference: [1] Patent: US5545535, 1996, A,
  • 11
  • [ 3034-38-6 ]
  • [ 80-48-8 ]
  • [ 3034-42-2 ]
Reference: [1] Patent: US4010176, 1977, A,
  • 12
  • [ 80-48-8 ]
  • [ 60832-72-6 ]
  • [ 169205-95-2 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 1999, vol. 35, # 1, p. 84 - 86
  • 13
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  • [ 80-48-8 ]
  • [ 5744-56-9 ]
Reference: [1] Chemische Berichte, 1926, vol. 59, p. 609
  • 14
  • [ 873-83-6 ]
  • [ 80-48-8 ]
  • [ 2434-53-9 ]
Reference: [1] Yakugaku Zasshi, 1954, vol. 74, p. 674,676,678,681[2] Chem.Abstr., 1954, p. 10743
  • 15
  • [ 13472-81-6 ]
  • [ 80-48-8 ]
  • [ 14529-54-5 ]
Reference: [1] Organic Process Research and Development, 2018, vol. 22, # 8, p. 978 - 990
[2] Patent: WO2018/109050, 2018, A1, . Location in patent: Paragraph 0224-0225
  • 16
  • [ 1789-95-3 ]
  • [ 80-48-8 ]
  • [ 18755-43-6 ]
  • [ 18755-44-7 ]
  • [ 599-91-7 ]
Reference: [1] Journal of Organic Chemistry, 1969, vol. 34, p. 681 - 685
  • 17
  • [ 104-86-9 ]
  • [ 80-48-8 ]
  • [ 104-11-0 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1989, p. 1881 - 1886
  • 18
  • [ 59564-59-9 ]
  • [ 80-48-8 ]
  • [ 67074-63-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1988, vol. 25, # 5, p. 1475 - 1479
  • 19
  • [ 480-66-0 ]
  • [ 80-48-8 ]
  • [ 90-24-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 23, p. 5025 - 5032
[2] Journal of Chemical Research, 2012, vol. 36, # 3, p. 121 - 122
  • 20
  • [ 591-20-8 ]
  • [ 80-48-8 ]
  • [ 2398-37-0 ]
Reference: [1] Journal of the Chemical Society, 1936, p. 50
  • 21
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  • [ 80-48-8 ]
  • [ 24134-09-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 4, p. 919 - 924
  • 22
  • [ 581-43-1 ]
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  • [ 5486-55-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1964, vol. 7, p. 519 - 524
  • 23
  • [ 2675-79-8 ]
  • [ 80-48-8 ]
  • [ 6443-69-2 ]
Reference: [1] Chemical Communications, 2017, vol. 53, # 73, p. 10180 - 10183
  • 24
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  • [ 312299-66-4 ]
  • [ 6443-69-2 ]
Reference: [1] Chemical Communications, 2017, vol. 53, # 73, p. 10180 - 10183
  • 25
  • [ 7304-32-7 ]
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  • [ 2965-22-2 ]
Reference: [1] Organic Letters, 2005, vol. 7, # 6, p. 1011 - 1014
  • 26
  • [ 107-04-0 ]
  • [ 80-48-8 ]
  • [ 80-41-1 ]
  • [ 19263-21-9 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 24, p. 5783 - 5785
[2] Journal of Organic Chemistry, 1988, vol. 53, # 24, p. 5783 - 5785
  • 27
  • [ 51329-15-8 ]
  • [ 80-48-8 ]
  • [ 25081-39-4 ]
Reference: [1] Chemical Communications, 2017, vol. 53, # 73, p. 10180 - 10183
  • 28
  • [ 5428-54-6 ]
  • [ 80-48-8 ]
  • [ 13120-77-9 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 2801
  • 29
  • [ 35030-98-9 ]
  • [ 80-48-8 ]
  • [ 1521-38-6 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1934, vol. &lt;5&gt; 1, p. 653,672
  • 30
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  • [ 4124-41-8 ]
Reference: [1] Journal of the Iranian Chemical Society, 2012, vol. 9, # 4, p. 507 - 512
  • 31
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  • [ 10506-59-9 ]
  • [ 4124-41-8 ]
  • [ 49829-22-3 ]
  • [ 76443-13-5 ]
  • [ 76443-14-6 ]
  • [ 77-78-1 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 284 - 289[2] Zhurnal Organicheskoi Khimii, 1982, vol. 18, # 2, p. 330 - 336
  • 32
  • [ 2233-18-3 ]
  • [ 80-48-8 ]
  • [ 39250-90-3 ]
Reference: [1] Organic Process Research and Development, 2015, vol. 19, # 1, p. 270 - 283
  • 33
  • [ 75-21-8 ]
  • [ 80-48-8 ]
  • [ 17178-10-8 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1967, vol. 710, p. 59 - 70
  • 34
  • [ 80-48-8 ]
  • [ 104-84-7 ]
  • [ 699-04-7 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1989, p. 1881 - 1886
  • 35
  • [ 110-86-1 ]
  • [ 80-48-8 ]
  • [ 24057-28-1 ]
Reference: [1] Heterocyclic Communications, 2013, vol. 19, # 1, p. 43 - 47
  • 36
  • [ 108-01-0 ]
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  • [ 55357-38-5 ]
YieldReaction ConditionsOperation in experiment
95% at 20℃; for 24 h; 22.3 g (250 mmol) of dimethylaminoethanol and 1 L of THF were placed in a four-necked flask (2 L), and the mixture was stirred at room temperature. 250 mL of a THF solution of 51.2 g (275 mol) of methyl tosylate was added dropwise and the mixture was stirred at room temperature for 24 hours. THF was distilled off, and the desired product was purified by recrystallization with 1 L of acetone. Colorless solid Yield 95percent.
Reference: [1] Russian Chemical Bulletin, 1998, vol. 47, # 8, p. 1547 - 1549
[2] Tetrahedron Letters, 2009, vol. 50, # 28, p. 4092 - 4095
[3] Patent: JP5751578, 2015, B2, . Location in patent: Paragraph 0017
[4] European Journal of Medicinal Chemistry, 2009, vol. 44, # 12, p. 4970 - 4977
[5] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1988, vol. 37, p. 2293 - 2296[6] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1988, # 11, p. 2542 - 2545
  • 37
  • [ 80-48-8 ]
  • [ 169205-95-2 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 1999, vol. 35, # 1, p. 84 - 86
  • 38
  • [ 80-48-8 ]
  • [ 60832-72-6 ]
  • [ 169205-95-2 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 1999, vol. 35, # 1, p. 84 - 86
  • 39
  • [ 80-48-8 ]
  • [ 160114-16-9 ]
  • [ 94055-76-2 ]
YieldReaction ConditionsOperation in experiment
85% at 20 - 60℃; Add 5.0 g (15.95 mmol) of intermediate 3 to the reaction flask at 20~30 °C.5.94 g of p-toluenesulfonic acid methyl ester (31.91 mmol), stir to 50-60 ° C, react for 20-24 h, add 10 mL of acetone for 30 minutes, filter, filter cake and add 20 mL of acetone to recrystallize to obtain metformin. 6.8 g, yield 85.0
Reference: [1] Patent: CN108440358, 2018, A, . Location in patent: Paragraph 0017; 0020; 0024
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 18, p. 3330 - 3336
  • 40
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  • [ 77897-02-0 ]
Reference: [1] Chemical Communications, 2017, vol. 53, # 73, p. 10180 - 10183
  • 41
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  • [ 86123-95-7 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With potassium hydroxide In toluene at 0 - 5℃; for 0.5 h;
Stage #2: With tetrabutylammomium bromide In toluene at 0 - 5℃; for 8 h;
In a 1000 mL three-necked flask,400 mL of toluene and 40 g of N-tert-butoxycarbonyl-D-serine (Boc-D-serine)The stirring temperature was lowered to 0-5 ° C,36.5 g of 30percent potassium hydroxide solution was added dropwise.After stirring for 30 minutes,Then 72.65 g of methyl p-toluenesulfonate was added,Tetrabutylammonium bromide 4g,Then 43.68 g of 50percent potassium hydroxide solution was added dropwise.After reaction at 0-5 ° C for 8 hours,Add water 200mL and layered,The aqueous layer was washed with 100 mL of toluene,Discard the organic layer.The combined aqueous layers were then cooled to below 15 [deg.] C and acidified with 50percent phosphoric acid to pH = 2-3.5,Extraction with dichloromethane (200 mL * 3)The combined organic layers were added 30g of anhydrous sodium sulfate and stirred overnight.The next day filterThe filtrate was concentrated to dryness under reduced pressure,42.9 g of light yellow oil,Yield: 100percent, HPLC purity: 98.0percent, Chiral purity: 99.4percent.
Reference: [1] Patent: CN106699595, 2017, A, . Location in patent: Paragraph 0036; 0037
  • 42
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  • [ 120511-72-0 ]
Reference: [1] Organic Preparations and Procedures International, 2008, vol. 40, # 5, p. 487 - 489
  • 43
  • [ 755039-54-4 ]
  • [ 80-48-8 ]
  • [ 755039-55-5 ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate In acetone for 2 h; Reflux; Inert atmosphere Step 11 (7R)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-5H-pteridin-6-one; (7R)-2-Chloro-8-cyclopentyl-7-ethyl-7,8-dihydro-5H-pteridin-6-one In (3.50 g, 12.50 mmol) was dissolved in 80 mL of acetone followed by the addition of methyl p-toluenesulfonate (3.40 g, 18.70 mmol) and potassium carbonate (3.45 g, 25 mmol). The resulting mixture was heated to reflux for 2 hours with stirring and then cooled down to room temperature. The reaction mxiture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (7R)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-5H-pteridin-6-one 1o (3.40 g, yield: 93.0percent) as a white solid. MS m/z (ESI): 295.4 [M+1]
93% With potassium carbonate In acetone for 2 h; Reflux Step 11
(7R)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-5H-pteridin-6-one
(7R)-2-Chloro-8-cyclopentyl-7-ethyl-7,8-dihydro-5H-pteridin-6-one 1n (3.50 g, 12.50 mmol) was dissolved in 80 mL of acetone followed by the addition of methyl p-toluenesulfonate (3.40 g, 18.70 mmol) and potassium carbonate (3.45 g, 25 mmol).
The resulting mixture was heated to reflux for 2 hours with stirring and then cooled down to room temperature.
The reaction mixture was filtered and the filtrate was concentrated under reduced pressure.
The resulting residue was purified by silica gel column chromatography to obtain the title compound (7R)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-5H-pteridin-6-one 1o (3.40 g, yield: 93.0percent) as a white solid.MS m/z (ESI): 295.4 [M+1]
Reference: [1] Patent: EP2481739, 2012, A1, . Location in patent: Page/Page column 21-22
[2] Patent: US2012/184543, 2012, A1, . Location in patent: Page/Page column 24
  • 44
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  • [ 880468-89-3 ]
YieldReaction ConditionsOperation in experiment
80% With tetrabutylammomium bromide; potassium hydroxide In toluene at -1 - 2℃; Toluene (820 mL), Intermediate III (50 g), methyl p-toluenesulfonate (63.5 g),Tetrabutylammonium bromide (5.4 g) was added and the mixture was cooled with stirring to -1 to 2 ° C. Potassium hydroxide aqueous solution (40 g / 34 mL) was added at -1 to 2 ° C, and the addition was completed in about 5 minutes. The addition was complete, continue to control the temperature at -1 ~ 2 reaction 4 ~ 4.5 hours (TLC detection or HPLC control) to stop the reaction. After completion of the reaction, water (400 mL) was added to separate the layers. Organic layer followed by 5percent phosphoric acid, saturated sodium bicarbonate, water each200mL wash. Decompression 40 ~ 45 ° C The solvent was evaporated to give an oil, the reaction was used directly for the next step. HPLC purity 95percent, chiral Purity 99.1percent.
60.97g With tetrabutylammomium bromide; potassium hydroxide In water; toluene at 20℃; for 3 h; Toluene (330 mL) was added sequentially to the 1 L reaction flask,The compound of formula II (20.00 g, 68 mmol)P-toluenesulfonic acid methyl ester (63.50 g, 340 mmol),Tetrabutylammonium bromide (2.63 g, 8.16 mmol),Stir evenly,An aqueous solution of potassium hydroxide (16.00 g of potassium hydroxide + 16 mL of water) was added at room temperature,Plus complete, room temperature reaction 3 hours.Reaction completed, adding water (160mL), stirring 5min, standing stratification, liquid separation,Organic layer followed by 5percent phosphoric acid(80 mL), water (160 mL x 2), and the organic layer was concentrated at 55 ° C under reduced pressure. The solvent was evaporated to give 60.97 g of an oil.The product of this example was the same as in Example 1 by isolation and identification.
38.5 g With tetrabutylammomium bromide; sodium hydroxide In water at 20℃; for 3 h; To a 1L reaction flask were sequentially added toluene (330 mL), Compound II (20.00 g, 68 mmol), methyl p-toluenesulfonate (38.10 g, 204 mmol), tetrabutylammonium bromide (2.63 g, 8.16 mmol), Stir well, add aqueous sodium hydroxide solution (16.00g of sodium hydroxide + 16mL of water) at room temperature, complete the addition, and react at room temperature for 3 hours. After the reaction is complete, add water (160 mL), stir for 5 min, stand for layering, separate the liquid, and use 5percent phosphoric acid in order for the organic layer.(80 mL) and water (160 mL×2) were washed. The organic layer was concentrated under reduced pressure at 55° C., and the solvent was evaporated to give 38.5 g of an oil.
38.5 g With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 20℃; for 3 h; Toluene (330 mL) was added sequentially to a 1L reaction flask,Compound II (20.00 g, 68 mmol),Methyl p-toluenesulfonate (38.10 g, 204 mmol),Tetrabutylammonium bromide (2.63 g, 8.16 mmol),Stir well,An aqueous solution of sodium hydroxide (16.00 g of sodium hydroxide + 16 mL of water) was added at room temperature.After the addition, the reaction was carried out at room temperature for 3 hours.After the reaction is complete, add water (160 mL) and stir for 5 min.Static stratification, liquid separation,The organic layer was successively washed with 5percent phosphoric acid (80 mL) and water (160 mL×2), and the organic layer was concentrated under reduced pressure at 55° C.After the solvent was distilled off, 38.5 g of an oil was obtained.

Reference: [1] Patent: CN106699605, 2017, A, . Location in patent: Paragraph 0043; 0044; 0046; 0048; 0049
[2] Patent: CN104892460, 2017, B, . Location in patent: Paragraph 0045; 0081; 0082; 0083; 0084; 0085-0092
[3] Patent: CN104892461, 2017, B, . Location in patent: Paragraph 0085; 0086; 0087
[4] Patent: CN105037209, 2017, B, . Location in patent: Sheet 0083; 0084; 0085
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  • [ 877676-50-1 ]
Reference: [1] Patent: US2012/184543, 2012, A1,
[2] Patent: EP2481739, 2012, A1,
[3] Patent: EP2481739, 2012, A1, . Location in patent: Page/Page column 58
[4] Patent: US2012/184543, 2012, A1, . Location in patent: Page/Page column 59
  • 46
  • [ 1417190-31-8 ]
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  • [ 1262417-94-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 17, p. 6875 - 6898
  • 47
  • [ 80-48-8 ]
  • [ 400827-68-1 ]
  • [ 400827-64-7 ]
YieldReaction ConditionsOperation in experiment
74.3%
Stage #1: for 12 h; Reflux
Stage #2: With pyridine; phosphorus pentachloride In dichloromethane at -10 - -5℃; for 2 h;
Stage #3: With hydrogenchloride In dichloromethane; 2-methyl-propan-1-ol; acetone at 25 - 30℃;
A glass round bottom flask was charged with 35g (51,7 mmol) of 5-Thia-1-azabicyclo[4.2.0]oct- 2-ene-2-carboxylic acid, 8-oxo-7-[(2-phenylacetyl)amino]-3-[[4-(4-pyridinyl)-2-thiazolyl]thio]-, diphenylmethyl ester, (6R,7R) and 75 mE of dichloromethane, at 25°C. To the obtained solution were added 48 mE (258,5 mmol) of methyl paratoluenesulphonate and the mixture was heated to reflux and maintained for 12 hours under reflux, then cooled to room temperature. In glass lined reactor were charged 32,3 g (155,1 mmol) of phosphorous pentachloride and 75 mE of dichloromethane. The obtained suspension was cooled to -5÷0°C and 12.3 g (155,1 mmol)of pyridine were added dropwise by maintaining the temperature at -5÷0°C, then the mixture was maintained under stifling for 15 minutes at the same temperature. To the mixture, cooled to -1 0÷-5°C, was carefully added the solution prepared in the round bottom flask, keeping the temperature between -1 0÷-5°C; the mixture thus obtained was maintained under stifling for 2 hours at the same temperature. 105 mE of isobutanol were carefully added, in about 30 minutes, by maintaining the temperature at -5°C0°C; the obtained mixture was heated at 28÷30°C and left to react at the same temperature for 3.5 hours. The mixture was concentrated under vacuum to 1/3 of its volume, diluted with 200 mE of acetone and maintained under stifling for 1 hour at 25÷30°C. 70 mE of 32percent hydrochloric acid were added, keeping the temperature in the range of 25÷30°C, and themixture was maintained under stirring overnight. The obtained suspension was filtered, the cake was washed with acetone (2 x 35 ml). The wet solid was dried under vacuum at 40°C overnight yielding 18.4 g (38,4 mmol) of 4-[2- [[(6R,7R)-7-amino-2-carboxy-8-oxo-5-thia- 1- azabicyclo [4.2.01 oct-2-en-3-yl]thio] -4-thiazolyl] -1 -methyl pyridinium, chloride, hydrochloride (1:1:1) as a crystalline solid. Yield 74,3percent.
Reference: [1] Patent: WO2016/128580, 2016, A1, . Location in patent: Page/Page column 21
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A500959[ 7575-93-1 ]

Methyl-D3p-toluenesulfonate

Reason: Stable Isotope

Related Functional Groups of
[ 80-48-8 ]

Aryls

Chemical Structure| 80-40-0

[ 80-40-0 ]

Ethyl 4-methylbenzenesulfonate

Similarity: 0.93

Chemical Structure| 24124-59-2

[ 24124-59-2 ]

Methylene bis(4-methylbenzenesulfonate)

Similarity: 0.93

Chemical Structure| 599-91-7

[ 599-91-7 ]

Propyl 4-methylbenzenesulfonate

Similarity: 0.92

Chemical Structure| 6315-52-2

[ 6315-52-2 ]

Ethane-1,2-diyl bis(4-methylbenzenesulfonate)

Similarity: 0.92

Chemical Structure| 778-28-9

[ 778-28-9 ]

Butyl 4-methylbenzenesulfonate

Similarity: 0.90

Sulfonates

Chemical Structure| 80-40-0

[ 80-40-0 ]

Ethyl 4-methylbenzenesulfonate

Similarity: 0.93

Chemical Structure| 24124-59-2

[ 24124-59-2 ]

Methylene bis(4-methylbenzenesulfonate)

Similarity: 0.93

Chemical Structure| 599-91-7

[ 599-91-7 ]

Propyl 4-methylbenzenesulfonate

Similarity: 0.92

Chemical Structure| 6315-52-2

[ 6315-52-2 ]

Ethane-1,2-diyl bis(4-methylbenzenesulfonate)

Similarity: 0.92

Chemical Structure| 778-28-9

[ 778-28-9 ]

Butyl 4-methylbenzenesulfonate

Similarity: 0.90