Home Cart 0 Sign in  

[ CAS No. 551-16-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 551-16-6
Chemical Structure| 551-16-6
Structure of 551-16-6 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 551-16-6 ]

Related Doc. of [ 551-16-6 ]

Alternatived Products of [ 551-16-6 ]

Product Details of [ 551-16-6 ]

CAS No. :551-16-6 MDL No. :MFCD00005176
Formula : C8H12N2O3S Boiling Point : -
Linear Structure Formula :- InChI Key :NGHVIOIJCVXTGV-ALEPSDHESA-N
M.W : 216.26 Pubchem ID :11082
Synonyms :
6-APA;NSC 50071;6β-Aminopenicillanic Acid;(+)-6-Aminopenicillanic Acid

Calculated chemistry of [ 551-16-6 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.75
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 55.46
TPSA : 108.93 Ų

Pharmacokinetics

GI absorption : High
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) : -9.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.3
Log Po/w (XLOGP3) : -2.08
Log Po/w (WLOGP) : -0.92
Log Po/w (MLOGP) : 0.08
Log Po/w (SILICOS-IT) : -0.83
Consensus Log Po/w : -0.49

Druglikeness

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

Water Solubility

Log S (ESOL) : 0.2
Solubility : 339.0 mg/ml ; 1.57 mol/l
Class : Highly soluble
Log S (Ali) : 0.32
Solubility : 451.0 mg/ml ; 2.09 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.31
Solubility : 441.0 mg/ml ; 2.04 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.72

Safety of [ 551-16-6 ]

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 [ 551-16-6 ]

* 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 [ 551-16-6 ]
  • Downstream synthetic route of [ 551-16-6 ]

[ 551-16-6 ] Synthesis Path-Upstream   1~35

  • 1
  • [ 87-08-1 ]
  • [ 551-16-6 ]
  • [ 122-59-8 ]
Reference: [1] Patent: US2005/20685, 2005, A1, . Location in patent: Page 2-3
  • 2
  • [ 61-33-6 ]
  • [ 551-16-6 ]
Reference: [1] Nippon Nogei Kagaku Kaishi, 1955, vol. 29, p. 404[2] Chem.Abstr., 1957, p. 8160
[3] J. agirc. chem. Soc. Japan, 1950, vol. 23, p. 411[4] Chem.Abstr., 1951, p. 1197
[5] Patent: WO2014/128538, 2014, A1, . Location in patent: Page/Page column 11; 12
  • 3
  • [ 129096-81-7 ]
  • [ 551-16-6 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 17, p. 5110 - 5117
  • 4
  • [ 55151-71-8 ]
  • [ 551-16-6 ]
Reference: [1] Journal of the American Chemical Society, 1975, vol. 97, p. 5582 - 5583
  • 5
  • [ 20425-27-8 ]
  • [ 551-16-6 ]
Reference: [1] Journal of the American Chemical Society, 1975, vol. 97, p. 5582 - 5583
  • 6
  • [ 47449-42-3 ]
  • [ 551-16-6 ]
Reference: [1] Journal of the American Chemical Society, 1975, vol. 97, p. 5582 - 5583
  • 7
  • [ 128971-90-4 ]
  • [ 551-16-6 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 17, p. 5110 - 5117
  • 8
  • [ 128971-96-0 ]
  • [ 551-16-6 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 17, p. 5110 - 5117
  • 9
  • [ 128971-91-5 ]
  • [ 551-16-6 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 17, p. 5110 - 5117
  • 10
  • [ 128971-92-6 ]
  • [ 551-16-6 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 17, p. 5110 - 5117
  • 11
  • [ 128971-93-7 ]
  • [ 551-16-6 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 17, p. 5110 - 5117
  • 12
  • [ 128971-94-8 ]
  • [ 551-16-6 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 17, p. 5110 - 5117
  • 13
  • [ 15139-36-3 ]
  • [ 551-16-6 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 17, p. 5110 - 5117
  • 14
  • [ 51056-25-8 ]
  • [ 551-16-6 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 17, p. 5110 - 5117
  • 15
  • [ 40124-92-3 ]
  • [ 551-16-6 ]
Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 5838[2] Journal of the American Chemical Society, 1962, vol. 84, p. 2893,2987
[3] Journal of the American Chemical Society, 1962, vol. 84, p. 2983,2987
[4] Journal of the American Chemical Society, 1962, vol. 84, p. 2983 - 2990
  • 16
  • [ 21027-18-9 ]
  • [ 551-16-6 ]
Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 5838[2] Journal of the American Chemical Society, 1962, vol. 84, p. 2893,2987
  • 17
  • [ 26787-78-0 ]
  • [ 551-16-6 ]
  • [ 6324-01-2 ]
Reference: [1] CrystEngComm, 2013, vol. 15, # 34, p. 6776 - 6781
  • 18
  • [ 26939-76-4 ]
  • [ 551-16-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2003, vol. 345, # 6-7, p. 783 - 789
  • 19
  • [ 113-98-4 ]
  • [ 551-16-6 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1970, vol. 89, p. 1081 - 1084
  • 20
  • [ 61-33-6 ]
  • [ 103-82-2 ]
  • [ 551-16-6 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1993, vol. 32, # 1, p. 40 - 43
  • 21
  • [ 69-53-4 ]
  • [ 551-16-6 ]
  • [ 875-74-1 ]
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2010, vol. 67, # 1-2, p. 21 - 28
  • 22
  • [ 551-16-6 ]
  • [ 701-99-5 ]
  • [ 132-98-9 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With sodium hydrogencarbonate In water; acetone at 10 - 15℃; for 0.333333 h;
Stage #2: With potassium 2-ethylhexanoate In butan-1-ol
To a cooled and stirred solution of 2.76 g (12.5 mmol) of 6-APA in 60 mL of water containing 5.25 g (62.5 mmol) of sodium bicarbonate, a solution of 2.76 g (16.2 mmol) phenoxyacetyl chloride in 5 mL of acetone was added in one minute. The resulting mixture was stirred vigorously during 20 min while the temperature was kept at 10-15 °C. The clear solution was extracted twice with 15 mL portions of methyl isobutyl ketone (MIBK). The clear aqueous solution was cooled to 5-10 °C and acidified to pH 2 with a cold 5.0 mol/L sulfuric acid solution. The acidified aqueous solution was extracted with 50 mL MIBK twice. The MIBK extract was separated, washed with cold water, and dried for 10 min over anhydrous sodium sulfate. After filtration, 10 mL of a 25percent solution of potassium 2-ethylhexanoate in butanol was added. The white crystalline material was collected by filtration, washed on the filter with dry acetone and dried in vacuum, yield 3.5 g (80percent) penicillin V as a white solid. Mp: 210-211 °C (dec.). 1H NMR (400 MHz, DMSO-d6): δ 8.42 (d, 1H, J = 8.0 Hz), 7.27 (m, 2H), 6.92 (m, 3H), 5.42 (dd, 1H, J = 8.0 Hz, 4.0 Hz), 5.40 (d, 1H, J = 4.0 Hz), 4.62 (d, 2H, J = 2.2 Hz), 3.88 (s, 1H), 1.52 (s, 3H), 1.46 (s, 3H); 13C NMR (100 MHz, DMSO-d6): δ 172.8, 169.0, 168.1, 158.1, 130.0, 121.7, 115.0, 74.6, 67.3, 66.7, 65.0, 57.8, 32.7, 27.8; HRMS (FAB) calcd. for C16H18KN2O5S [M+H]+: m/z 389.0584; found: 389.0995.
Reference: [1] Chinese Chemical Letters, 2015, vol. 26, # 1, p. 113 - 117
  • 23
  • [ 551-16-6 ]
  • [ 132-98-9 ]
Reference: [1] Patent: WO2014/71283, 2014, A1,
  • 24
  • [ 15231-78-4 ]
  • [ 551-16-6 ]
  • [ 17879-45-7 ]
  • [ 95985-46-9 ]
  • [ 4800-94-6 ]
Reference: [1] Patent: US4066664, 1978, A,
  • 25
  • [ 551-16-6 ]
  • [ 40125-73-3 ]
  • [ 28002-18-8 ]
YieldReaction ConditionsOperation in experiment
69.42% With triethylamine In ethanol; 1,2-dichloro-ethane; acetone at 12℃; for 1.5 h; D(-)-methylbenzylamoxicillin sodium was prepared in the same manner as in Example 1 (1) except that the amount of 6-aminopenicillanic acid, the temperature of addition of trimethylamine and the reaction time were obtained, and the results of the experiment are shown in Table 2
65%
Stage #1: With sodium hydroxide In diethyl ether; water; acetone at -5 - 0℃; for 1 h;
Stage #2: With sodium isooctanoate In diethyl ether; butan-1-ol at -25℃; for 0.5 h;
30 g of 6-aminopenicillanic acid (6-APA) was suspended in acetone-water solution and cooled to -5 ° C, sodium hydroxide solution of mass concentration 10percent to adjust the pH to 7, so that 6-APA was completely dissolved , sulfophenylacetyl chloride obtained in step (5) is configured as a diethyl ether solution, in an ice bath of -5 ~ 0 ° C and stirring conditions, 40ml 40g of sulfophenylacetyl chloride in ether was added dropwise to an acetone-water solution of 6-aminopenicillanic acid, dripping completed , 10percent aqueous sodium hydroxide solution was used to adjust the pH to 2.5, the reaction was stirred for 60min at low temperature; (7) Preparation of D- (-) -α- sulbenicillin sodium: The reaction mixture of step (6) was washed with diethyl ether (70ml, 2 times each), then with n-butanol (100ml, 3 times), the organic phases were combined and the organic phase was washed with 20 mL of saturated saline to give the extracted N-butanol solution of diastereomeric isomer sulbenicillin, solution was cooled to -25 ° C, a white solid precipitated after 30 minutes, the filtrate was filtered and the filtrate was dried over anhydrous sodium sulfate to give -butanol solution of D - (-)-a - Sulbenicillin, then, a n-butanol solution of sodium isooctanoate in a mass concentration of 10percent was added to carry out a salt reaction to a pH of 6, finally, 200ml of ethanol precipitated a white solid, filtered and dried to give D- (-) -α- sulbenicillin sodium. sulbenicillin sodium product was obtained in the above method, after testing, the purity of up to 95.5percent, mp is 250 ~ 252 ° C, through the tracking test during the reaction, the yield of sulfobenzyl chloride was as high as 93percent and the yield of sulbenicillin sodium was as high as 65.1percent.
59.9% With sodium hydroxide In 2-methyltetrahydrofuran; ethanol; acetic acid butyl ester; water at 15 - 20℃; for 0.0333333 h; (2) 20.5 g of 6-APA was added to a mixed solvent of 50 mL of water, 29 mL of ethanol, and 10 mL of 2-methyltetrahydrofuran.Keep the temperature at 15 °C,Then add 10percent sodium hydroxide solution to adjust the pH to 7.0.Stir at 15 ° C until the solid is completely dissolved,While maintaining the temperature, a solution of 31.2 g of α-sulfophenylacetyl chloride in butyl acetate was added dropwise.The butyl acetate solution of α-sulfophenylacetyl chloride is uniformly added within 30 minutes.The reaction solution was maintained at pH 7.0 and allowed to react at room temperature for 20 minutes.Obtaining crude benzylicillin sodium;(3) adding dilute hydrochloric acid to the solution of the crude sulficillin sodium obtained above at room temperature to adjust the pH to1.0, then add n-butanol, wherein the volume ratio of n-butanol to sulficillin sodium crude solution is 3:0.8, layered, takenMachine phase extract to obtain benzoicillin organic solution; add in benzylicillin organic solution at a temperature of 5 ° CThe mass percentage concentration is 25percent sodium bicarbonate solution, wherein the ratio of the substance of benzylicillin to sodium bicarbonate is 1:2.0, and the temperature is stirred.Mix for 30 minutes, let stand for layering, separate the water layer, then wash the water layer with diethyl ether for 2 times, then add activated carbon to the water layer for 20 minutes.The bell was filtered to remove charcoal, and the filtrate was freeze-dried to obtain 32.6 g of benzylicillin sodium, the yield was 74.5percent, and the total yield was 59.9percent. PurityIt is 98.5percent.
Reference: [1] Patent: CN105218562, 2016, A, . Location in patent: Paragraph 0035; 0036; 0037
[2] Patent: CN107383060, 2017, A, . Location in patent: Paragraph 0018; 0019
[3] Patent: CN108373475, 2018, A, . Location in patent: Paragraph 0074; 0076; 0077
  • 26
  • [ 551-16-6 ]
  • [ 41360-32-1 ]
  • [ 28002-18-8 ]
YieldReaction ConditionsOperation in experiment
88.1%
Stage #1: With triethanolamine; 1,1'-carbonyldiimidazole In dichloromethane; toluene at -10℃; for 1.5 h;
Stage #2: at -5 - 10℃; for 0.75 h;
Stage #3: With sodium hydroxide In water
150 g of sulfophenylacetic acid was dissolved in a mixed solvent of 500 mL of dichloromethane and toluene, and the volume ratioofdichloromethane to toluenewas 1.5:4.0, and the mixture was rapidly stirred, and then 120 mL of triethanolamine was added thereto to clarify the solution.The temperature was lowered to -10 ° C to add70.6 g ofcarbonyl diimidazole, and the reaction was kept at -10 ° C for 1.5 h to prepare a mixed acyl imidazoylating agent solution, which was chilled at -15 ° C for use.Preparation of D-(-)-α-sulfacillin sodium: 40 g (0.25 mol) of 6-APA was suspended in amixed solution of300 mL of water-acetone-isopropanol in a volume ratio of 1.2:1:2.The temperature was lowered to -5 ° C, and pH 8 was adjusted with triethanolamine water to completely dissolve 6-APA.Under ice bath, a mixed acyl imidazoylating agent solution was added dropwise to the above solution at a dropping rate of 8percent by volume per minute, and the stirring was continued for 10 minutes while maintaining 10 °C.The reaction solution was washed with diethyl ether (70 mL × 2), n-butanol (100 mL ×3), and the organic phase was combined and washed with 20 mL of saturated aqueous sodium chloride to obtain the extract of the diastereomeric Butanolsolution.Decolorized with charcoal, 0.22um membrane filter, pharmaceutical grades of isopropanol was added a pharmaceutical grade methanol mixed organic solvent having a volumevolume ratio of 2.5: 1.8, after the cold reflux 2.5h, controlling the temperature of 8 , and the solution frozen -15 deg.] C, about 30 min the precipitatedwhite solid was filtered, the filtrate was dried over anhydrous sodium sulfate to give D - (-) - α- sulbenicillin alcohol solution, then added with water for injection wasplaced in a 10percent sodium hydroxide solution The pH was adjusted to 6-7, and lyophilized to give 35.2 g of a white solid compound, yield:88.1percent,
84%
Stage #1: With propionyl chloride; triethylamine In dichloromethane at 0 - 25℃; for 3 h;
Stage #2: With 2,2,2-trifluoro-N,N-bis(trimethylsilyl)-acetamide In ethyl acetate at 50℃; for 2 h; Inert atmosphere
Stage #3: With hydrogenchloride; sodium isooctanoate In ethanol; water at 0 - 25℃; for 0.75 h; Reflux
(1) Dissolving 216 g (1 mol) of sulfoacetic acid in anhydrous 1000 ml of dichloromethane,After adding 202.4 g (2.2 mol) of propionyl chloride,Cold to 0-5 ° C,449.5 g (4.45 mol) of triethylamine was added dropwise, and after completion, the reaction was carried out at 25 ° C for 3 hours.The reaction solution was transferred to a separatory funnel, washed with water, extracted with dichloromethane, and concentrated to give a mixed acid.(2) Weigh 202.3 g (0.85 mol) of 6-APA and 243.3 g (1.19 mol)N,N-bis(trimethylsilyl)-2,2,2-trifluoroacetamide in the reaction flask,After vacuuming, nitrogen gas was applied, and 1200 ml of ethyl acetate was added as a solvent, and the mixture was heated to about 50 ° C for 2 hours. The reaction was completed, lowered to room temperature, washed with water, extracted with ethyl acetate, and then dried and concentrated.(3) using ethanol as a solvent,Cool down to 0-5 ° C,Slowly adding step (1) to obtain a mixed anhydride and 6-APA protected by step (2),Insulation reaction for 45 minutes,Acidified with hydrochloric acid, raised to 25 ° C,Add sodium isooctanoate and naturally crystallize after stirring.filter. Take the filter cake in the reaction flask,Add 1600ml of ethanol-water (v/v=1/2) mixed solvent,The temperature was raised to reflux, and 75 g of activated carbon was added to stir and decolorize for 20 minutes.The mixture was filtered while hot, and then crystallized to obtain 384.7 g of sulphacillin sodium in a yield of 84percent.
Reference: [1] Patent: CN108084207, 2018, A, . Location in patent: Paragraph 0025-0031
[2] Patent: CN108373475, 2018, A, . Location in patent: Paragraph 0078; 0079
  • 27
  • [ 551-16-6 ]
  • [ 28002-18-8 ]
YieldReaction ConditionsOperation in experiment
91.5%
Stage #1: With N,O-bis-(trimethylsilyl)-acetamide In acetone at 30 - 35℃; for 3 h;
Stage #2: at 40 - 45℃; for 5 h;
Stage #3: With sodium 2-ethylhexanoic acid In water; acetone at 5 - 20℃; for 2 h;
1) 21.63 g (0.1 mol) of 6-APA was added to 100 g of acetone, 20.4 g (0.1 mol) of BSA was added, and the mixture was heated to 30-35 ° C for 3 hours, the reaction system was clarified, and 26.90 g (0.105 mol) of the intermediate was added. Z1, the temperature was raised from 40 ° C to 45 ° C for 5 hours, and the reaction system was clarified. 2) The temperature was lowered to 5 ° C, 43.26 g of water was added, and the mixture was stirred for 1 hour, and 49.86 g (0.3 mol) of sodium isooctanoate in 246.00 g of acetone was added thereto, and the mixture was stirred and crystallized at 20 ° C for 2 hours, and filtered. The solid was dried at 30 ° C for 20 hours. The sulficillin sodium solid was 41.95 g, the yield was 91.5percent, and the purity was 99.4percent.
Reference: [1] Patent: CN108752311, 2018, A, . Location in patent: Paragraph 0071-0076
  • 28
  • [ 551-16-6 ]
  • [ 28002-18-8 ]
Reference: [1] Patent: CN108373475, 2018, A,
  • 29
  • [ 551-16-6 ]
  • [ 28002-18-8 ]
Reference: [1] Patent: CN107641130, 2018, A,
  • 30
  • [ 551-16-6 ]
  • [ 1847-24-1 ]
Reference: [1] Patent: WO2012/164355, 2012, A1, . Location in patent: Page/Page column 11
  • 31
  • [ 551-16-6 ]
  • [ 25629-50-9 ]
  • [ 642-78-4 ]
Reference: [1] Patent: WO2012/164355, 2012, A1, . Location in patent: Page/Page column 9-10
  • 32
  • [ 551-16-6 ]
  • [ 37091-70-6 ]
  • [ 37091-66-0 ]
Reference: [1] European Journal of Medicinal Chemistry, 1982, vol. 17, # 1, p. 59 - 63
  • 33
  • [ 551-16-6 ]
  • [ 42057-28-3 ]
  • [ 42057-22-7 ]
Reference: [1] Arzneimittel Forschung, 1983, vol. 33, # 1, p. 88 - 90
  • 34
  • [ 551-16-6 ]
  • [ 87579-78-0 ]
Reference: [1] Synthesis, 2005, # 3, p. 442 - 446
[2] Antimicrobial Agents and Chemotherapy, 2012, vol. 56, # 5, p. 2713 - 2718
[3] Patent: CN106967089, 2017, A,
[4] Patent: CN108264519, 2018, A,
  • 35
  • [ 551-16-6 ]
  • [ 87579-78-0 ]
Reference: [1] Patent: CN108250218, 2018, A,
Same Skeleton Products
Historical Records