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Chemical Structure| 957-68-6
Chemical Structure| 957-68-6
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Product Details of [ 957-68-6 ]

CAS No. :957-68-6 MDL No. :MFCD00005177
Formula : C10H12N2O5S Boiling Point : -
Linear Structure Formula :- InChI Key :HSHGZXNAXBPPDL-HZGVNTEJSA-N
M.W : 272.28 Pubchem ID :441328
Synonyms :
7-ACA

Calculated chemistry of [ 957-68-6 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 4
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 65.85
TPSA : 135.23 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -10.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.99
Log Po/w (XLOGP3) : -4.03
Log Po/w (WLOGP) : -1.25
Log Po/w (MLOGP) : -0.29
Log Po/w (SILICOS-IT) : -0.84
Consensus Log Po/w : -1.08

Druglikeness

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

Water Solubility

Log S (ESOL) : 1.27
Solubility : 5130.0 mg/ml ; 18.8 mol/l
Class : Highly soluble
Log S (Ali) : 1.79
Solubility : 16800.0 mg/ml ; 61.8 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.12
Solubility : 357.0 mg/ml ; 1.31 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 4.13

Safety of [ 957-68-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 957-68-6 ]

* 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 [ 957-68-6 ]
  • Downstream synthetic route of [ 957-68-6 ]

[ 957-68-6 ] Synthesis Path-Upstream   1~31

  • 1
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Reference: [1] Advanced Synthesis and Catalysis, 2005, vol. 347, # 14, p. 1804 - 1810
  • 2
  • [ 27920-90-7 ]
  • [ 110-94-1 ]
  • [ 957-68-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2005, vol. 347, # 14, p. 1804 - 1810
  • 3
  • [ 28242-83-3 ]
  • [ 3184-35-8 ]
  • [ 957-68-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2005, vol. 347, # 14, p. 1804 - 1810
  • 4
  • [ 61-24-5 ]
  • [ 957-68-6 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 26, p. 9099 - 9106
[2] Tetrahedron Letters, 1997, vol. 38, # 26, p. 4693 - 4696
[3] Advanced Synthesis and Catalysis, 2005, vol. 347, # 1, p. 121 - 128
[4] Advanced Synthesis and Catalysis, 2005, vol. 347, # 14, p. 1804 - 1810
[5] Advanced Synthesis and Catalysis, 2005, vol. 347, # 14, p. 1804 - 1810
[6] Advanced Synthesis and Catalysis, 2005, vol. 347, # 14, p. 1804 - 1810
[7] Biocatalysis and Biotransformation, 2015, vol. 33, # 5-6, p. 250 - 259
  • 5
  • [ 51762-04-0 ]
  • [ 957-68-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 2, p. 343 - 348
  • 6
  • [ 27920-90-7 ]
  • [ 957-68-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2003, vol. 345, # 6-7, p. 783 - 789
[2] Advanced Synthesis and Catalysis, 2008, vol. 350, # 2, p. 343 - 348
[3] Journal of Molecular Catalysis B: Enzymatic, 2012, vol. 76, p. 52 - 58
  • 7
  • [ 64-19-7 ]
  • [ 107-10-8 ]
  • [ 957-68-6 ]
Reference: [1] Journal of the American Chemical Society, 1984, vol. 106, # 13, p. 3820 - 3825
  • 8
  • [ 27266-61-1 ]
  • [ 957-68-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 12, p. 4545 - 4547
  • 9
  • [ 28242-83-3 ]
  • [ 957-68-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 2, p. 343 - 348
  • 10
  • [ 3595-18-4 ]
  • [ 957-68-6 ]
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2012, vol. 76, p. 52 - 58
  • 11
  • [ 13183-79-4 ]
  • [ 957-68-6 ]
  • [ 24209-38-9 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: at 10 - 12℃; for 0.166667 h;
Stage #2: at 25℃; for 0.75 h;
Stage #3: With chloroacetyl chloride In N,N-dimethyl-formamide at 0℃; for 0.75 h;
Into a 1000ml four-necked flask was added 132ml (141.1g, 1.57mol) dimethyl carbonate, 162g boron trifluoride-dimethyl carbonate complex, was added at 10-12 deg. C 21.5g (0.185mol) 1-methyl-5-mercaptotetrazole, after stirring for 10min was added 50g (0.184mol) 7-aminocephalosporanic acid (7-ACA), reacted at 25 deg. C, after 45min, cooled to 0 deg. C, was added dropwise 32g (0.283mol) of chloroacetyl chloride in 37ml N'N- dimethylformamide solution, the reaction was kept for 45min, the reaction mixture was added with 300ml of water and 300ml of dimethyl carbonate then stirred, separated and the aqueous layer was extracted with 400ml of dimethyl carbonate, dimethyl carbonate layers combined, added 5g active carbon for 30min, a solution of triethylamine in dimethyl carbonate was added dropwise, adjusted to pH 6.8 at 0 -5 deg. C crystallization for 2h, filtration, the filter cake was dried in vacuo at 45 deg. C, to obtain 67g (0.180mol) 7-aminocephalosporanic triazine (7-ACT), a yield of 98percent.
91.3% With boron trifluoride diethyl etherate In acetonitrile at 50℃; for 2.5 h; 5-Mercapto-1-methyl-1H-tetrazole (6.32 g, 54.48 mmol) and7-ACA (4, 14.8 g, 54.41 mmol) were successively added toa stirred solution of BF3·Et2O (23.6 g) in anhydrous acetonitrile(75 mL). The resulting solution was allowed to reactat 50 °C for 2.5 h. After cooling in an ice-bath, the reactionsolution was diluted with H2O (75 mL) and adjusted to pH4.0 by the addition of 28 percent NH4OH. Crystals that precipitatedwere collected by filtration, and washed with waterand then acetone, to give 5 (16.3 g, 91.3 percent) as earth-yellowsolid. m.p.: 207–209 °C [lit. [37, 38]: 224–226 °C (dec.)].IR (KBr): 3423, 3170, 1803, 1735, 1618, 1542, 1411, 1342, 1084 cm−1. 1H NMR (400 MHz, DMSO-d6): δ = 3.56 (d,2J = −18 Hz, 1H, H-4), 3.73 (d, 2J = −18 Hz, 1H, H-4),3.93 (s, 3H, CH3), 4.20 (d, 2J = −13.6 Hz, 1H, CH2), 4.36(d, 2J = −13.6 Hz, 1H, CH2), 4.78 (d, 3J = 5.2 Hz, 1H, H-6),4.96 (d, 3J = 5.2 Hz, 1H, H-7).
91.3% With boron trifluoride diethyl etherate In acetonitrile at 50℃; for 2.5 h; 1) 7-TMCA (II): A mixture of 7-ACA (14.8g, 54.41mmol), mercapto tetrazole (6.32g, 54.48mmol) and BF3· Et2O (23.6g) in anhydrous acetonitrile (75mL) The reaction solution was stirred for 50 2.5h.The reaction solution was cooled to 0 deg.] C, was added water (75mL), and treated with aqueous ammonia solution was adjusted pH = 4, filtered, and the filter cake was washed successively with water and acetone to give a yellow solid product II (16.3g, 91.3percent).
Reference: [1] Patent: CN105330677, 2016, A, . Location in patent: Paragraph 0024
[2] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 12, p. 5534 - 5538
[3] Journal of the Iranian Chemical Society, 2016, vol. 13, # 6, p. 1019 - 1025
[4] Patent: CN105585580, 2016, A, . Location in patent: Paragraph 0007; 0031; 0032; 0033
[5] Journal of Heterocyclic Chemistry, 1989, vol. 26, # 2, p. 461 - 464
[6] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 12, p. 5534 - 5538
[7] Pharmazie, 1987, vol. 42, # 3, p. 160 - 161
  • 12
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YieldReaction ConditionsOperation in experiment
324 g With acetonitrile boron trifluoride complex In acetonitrile at 30℃; for 2 h; (1) 1.5 L of acetonitrile, 300 g of 3-acetoxymethyl-5-thio-7-amino-8-oxo-1-azabicyclooct-2-ene-2-carboxylic acid, 1.5 kg of 5-Mercapto-1- methyltetrazole, 1.4 L of Borontrifluoride / acetonitrile complex were mixed, then heated to 40 ° C, and rapidly stirred for 1 h. after completion of reaction, it was cooled to 2 ° C. The reaction solution was mixed with 2.25 L of purified water pre-cooled to 5 ° C and slowly stirred until the crystal was precipitated, then stir again for 30 min, add 10percent ammonia to adjust the pH to 3.4, control the temperature to 0 ~ 5 ° C, and raise the crystal for 3h. Filtration carried out, then washed twice with 1.5L of acetone, and vacuum drying to obtain white crystalline powder (6R, 7R) -7-amino-3 [(Z) -2- (4- methylthiazole) -5- yl] Vinyl-8-oxo-5-thia-1-azabicyclo [4.2.0] oct-2-ene-2-carboxylic acid 324g
Reference: [1] Patent: CN106699775, 2017, A, . Location in patent: Paragraph 0029; 0030
  • 13
  • [ 1918-77-0 ]
  • [ 957-68-6 ]
  • [ 153-61-7 ]
YieldReaction ConditionsOperation in experiment
85% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 30℃; for 2 h; Green chemistry In a 2000 ml three-necked flask, 71 g of 2-thiopheneacetic acid was added.Organic solvent dichloromethane 550ml,Then add 90 ml of triethylamine and EDC (1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride) 190 g.Then control the temperature to slowly add 7-ACA 110g under the condition of 30°C,And control the condensation reaction at a temperature of 30°C for 2 hours.After the condensation reaction was completed, a 10percent wt hydrochloric acid solution was added dropwise to the reaction solution to adjust the ph value to 1.5-2.0. Then,Standing, delaminating, collecting organic phases, The collected organic phase was quickly added to 1000 ml of aqueous sodium bicarbonate and the pH was adjusted to 6.5-7.0.Standing, stratified, Collect the water phase,Then control the temperature at 20-25 degrees Celsius slowly adding 10wtpercent hydrochloric acid to adjust the system ph value to 1.5,Then stir and crystallize for 1 hour, cool down to 10°C, and filter to obtain wet product.Drying at 40°C gives a white solid productCephalothin 170g, yield 85percent.
Reference: [1] Patent: CN107793431, 2018, A, . Location in patent: Paragraph 0012; 0013; 0014; 0015; 0016; 0017; 0018; 0019
  • 14
  • [ 19432-68-9 ]
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  • [ 153-61-7 ]
Reference: [1] Patent: CN104447800, 2016, B, . Location in patent: Paragraph 0015; 0047-0048
  • 15
  • [ 93799-48-5 ]
  • [ 957-68-6 ]
  • [ 153-61-7 ]
YieldReaction ConditionsOperation in experiment
154 g at 15 - 25℃; for 1 h; Irradiation To a 2000 mL three-necked flask was added 71 g (0.5 mol) of 2-thiopheneacetic acid,Organic solvent ethylene glycol dimethyl ether 600mL,Then add 80 mL of morpholine andTrifluoroacetic acid succinimidyl ester212 g (1.0 mol), and then the temperature was programmed at a temperature of 10 ° C to 15 ° C.4.5 hours, the reaction was completed, and the reaction solution containing the active ester was obtained by filtration,The reaction solution containing the active ester was slowly added dropwise to a prefabricated solution containing 136 g (0.5 mol) of 7-ACA in 1000 mL of ethylene glycol dimethyl ether,The temperature was irradiated at 15 ° C to 25 ° C for 1 hour,After the condensation reaction was completed, the reaction solution was added dropwise with 10percent by weight hydrochloric acid solution, the pH was adjusted to 1.5 to 2.0, and then allowed to stand, the layers were collected, the organic phase was collected,The collected organic phase was rapidly added to 1000 mL of aqueous sodium bicarbonate solution, the pH was adjusted to 6.5 to 7.0,The temperature was then controlled at 20 ° C to 25 ° C, 10percent by weight hydrochloric acid was slowly added, the pH of the system was adjusted to 1.5, stirred, the crystals were raised for 1 hour,The filtrate was filtered to give a wet product and dried at 40 & lt; 0 & gt; C154 g of product was obtained as a white solid, cefuroxime, in a yield of 96.9percent.
Reference: [1] Patent: CN104610280, 2017, B, . Location in patent: Paragraph 0020; 0021; 0022; 0023; 0024; 0025; 0026
  • 16
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  • [ 957-68-6 ]
  • [ 153-61-7 ]
Reference: [1] Patent: US4139702, 1979, A,
  • 17
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  • [ 22252-43-3 ]
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 20, p. 3899 - 3901
  • 18
  • [ 957-68-6 ]
  • [ 22252-43-3 ]
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 20, p. 3899 - 3901
  • 19
  • [ 957-68-6 ]
  • [ 55633-19-7 ]
  • [ 21732-17-2 ]
  • [ 32510-61-5 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 26, p. 9099 - 9106
[2] Advanced Synthesis and Catalysis, 2005, vol. 347, # 1, p. 121 - 128
  • 20
  • [ 39098-97-0 ]
  • [ 957-68-6 ]
  • [ 58-71-9 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1988, p. 1815 - 1822
  • 21
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  • [ 35607-66-0 ]
Reference: [1] Patent: CN105218563, 2016, A,
[2] Patent: CN104447800, 2016, B,
  • 22
  • [ 957-68-6 ]
  • [ 27164-46-1 ]
Reference: [1] Patent: CN105541870, 2016, A,
  • 23
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  • [ 15690-38-7 ]
YieldReaction ConditionsOperation in experiment
90.1% With tetrabutyl-ammonium chloride; sodium hydroxide In methanol; water at -5 - 5℃; Weigh 7-ACA 27.2g (0.1mol),Add 50mL of methanol and 50mL of water,Add 3.0g tetra-n-butane at -5-5°CAmmonium chloride stirring to dissolve,Maintain the addition of 2mol/L sodium hydroxide solution 105mL at this temperature.After dripping, maintain the temperature and continue stirring for 0.5-1 hour.Then add 30percent hydrochloric acid to adjust the pH to neutral,Precipitation of solids, suction filtration, anhydrous ethanol washing,20.7g of dried white solidYield 90.1percent,HPLC purity analysis 97.35percent (area normalization method),Lactone impurity 0.33percent.
86% With water; sodium hydroxide In methanol at -20 - -10℃; In the first step: 20 g of 7-ACA was added to a solution consisting of 140 mL of methanol and 140 mL of water, cooled to -10 to -20 ° C, 15.6 mL of a 10 mol / L NaOH solution was added dropwise, stirred for 10 min, The reaction solution was slowly neutralized with 1 mol / L HCl solution to pH to pH 3. After filtration, the filter cake was washed successively with methanol, acetone and diethyl ether and dried in vacuo to give 14.5 g White 7-AHCA, the yield was 86percent;
Reference: [1] Patent: CN105131017, 2017, B, . Location in patent: Paragraph 0041-0042
[2] Synthetic Communications, 2003, vol. 33, # 14, p. 2475 - 2482
[3] Patent: CN106083894, 2016, A, . Location in patent: Paragraph 0045; 0054; 0055; 0056; 0057
[4] Synthesis, 2012, vol. 2012, # 2, p. 207 - 214
[5] Farmaco, 2003, vol. 58, # 6, p. 409 - 418
[6] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 21, p. 5534 - 5537
[7] Journal of Medicinal Chemistry, 1984, vol. 27, # 5, p. 694 - 700
[8] Journal of Medicinal Chemistry, 1974, vol. 17, p. 1312 - 1315
[9] Canadian Journal of Chemistry, 1993, vol. 71, # 6, p. 896 - 906
[10] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 9, p. 853 - 857
[11] Farmaco, 2001, vol. 56, # 8, p. 629 - 631
[12] Organic Process Research and Development, 2009, vol. 13, # 4, p. 815 - 819
[13] Patent: CN105254650, 2016, A, . Location in patent: Paragraph 0043
  • 24
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  • [ 56796-39-5 ]
Reference: [1] Patent: CN105330677, 2016, A,
  • 25
  • [ 957-68-6 ]
  • [ 56610-72-1 ]
Reference: [1] Journal of the Iranian Chemical Society, 2016, vol. 13, # 6, p. 1019 - 1025
[2] Patent: CN105585580, 2016, A,
  • 26
  • [ 110-86-1 ]
  • [ 354808-44-9 ]
  • [ 957-68-6 ]
  • [ 72558-82-8 ]
YieldReaction ConditionsOperation in experiment
98.9% at -16℃; for 2 h; Sonication; Industrial scale One-pot method of this invention a method of preparation Ceftazidime, comprising the steps of: weighing 272kg7-amino cephalosporanic acid (7-ACA, compound I, MW272,1000mol), 360.8 kg cephalosporin he [...] hydrochloride (compound II, MW328,1100mol) and 1027 kg pyridine (MW79,13000mol), placed in an ultrasonic reactor, -16°C, ultrasonic oscillation 800W 2 hours, adjusted to pH 4.2, is added to reaction solution 190.4 kg acetone, separating white solid, 5 °C cold water washing, 50 °C vacuum drying 5 hours to obtain the 629 kg (MW636) Ceftazidime, yield 98.9percent, purity 99.9percent or more, the single hetero less than 0.01percent, acetone residual quantity is less than 0.01percent.
Reference: [1] Patent: CN105585582, 2016, A, . Location in patent: Paragraph 0031; 0032
  • 27
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  • [ 72558-82-8 ]
Reference: [1] Patent: CN104892638, 2017, B,
[2] Patent: CN104892638, 2017, B,
[3] Patent: CN104892638, 2017, B,
  • 28
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  • [ 62893-19-0 ]
Reference: [1] Patent: CN105566350, 2016, A,
[2] Patent: CN103641847, 2016, B,
  • 29
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  • [ 87239-81-4 ]
Reference: [1] Farmaco, 2003, vol. 58, # 5, p. 363 - 369
[2] Patent: WO2013/41999, 2013, A1,
  • 30
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  • [ 64485-93-4 ]
Reference: [1] Patent: CN105646535, 2016, A, . Location in patent: Paragraph 0025; 0026; 0027; 0028; 0029; 0030; 0031-0033
  • 31
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  • [ 80756-85-0 ]
  • [ 957-68-6 ]
  • [ 98753-19-6 ]
YieldReaction ConditionsOperation in experiment
99% for 0.0666667 h; Microwave irradiation The method for synthesizing cefpirome sulfuric acid by microwave method according to the present invention,Comprising the steps of:(1) 7-aminocephalosporanic acid (2.72 g, 7-ACA, Compound I, MW272, 0.01 mol) and AE-activity(AEMA, Compound VII, MW 350, 0.011 mol) was mixed and homogeneously ground.(Compound IV, MW 119, 0.011 mol) and concentrated sulfuric acid (10.88 g, 98percent by weight) were added to the solution, followed by the addition of 2,30 g of 2,3-cyclopentenopyridine.(2) 300W microwave reaction for 1 minute,450W microwave reaction for 1 minute,750W microwave reaction for 2 minutes;(3) After completion of the reaction,The reaction residue was added to 29.92 g of deionized water,Mixing and filtering,Take filtrate,The solvent was removed,A white solid,50 & lt; 0 & gt; C for 4 hours under vacuum,That is to get the cefpirome sulfuric acid 5.09g (MW514),Yield 99.0percentPurity 99.9percent or more.
Reference: [1] Patent: CN105646542, 2016, A, . Location in patent: Paragraph 0027; 0040; 0041; 0042; 0043; 0044; 0045
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