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[ CAS No. 17794-48-8 ] {[proInfo.proName]}

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Chemical Structure| 17794-48-8
Chemical Structure| 17794-48-8
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Product Details of [ 17794-48-8 ]

CAS No. :17794-48-8 MDL No. :MFCD00029782
Formula : C10H8F3NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :ZDGGJQMSELMHLK-UHFFFAOYSA-N
M.W : 247.17 Pubchem ID :2777432
Synonyms :

Calculated chemistry of [ 17794-48-8 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 5
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 51.02
TPSA : 66.4 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.23
Log Po/w (XLOGP3) : 2.11
Log Po/w (WLOGP) : 2.67
Log Po/w (MLOGP) : 1.84
Log Po/w (SILICOS-IT) : 1.78
Consensus Log Po/w : 1.93

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.63
Solubility : 0.576 mg/ml ; 0.00233 mol/l
Class : Soluble
Log S (Ali) : -3.14
Solubility : 0.181 mg/ml ; 0.000733 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.07
Solubility : 0.211 mg/ml ; 0.000853 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.52

Safety of [ 17794-48-8 ]

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

Application In Synthesis of [ 17794-48-8 ]

* 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 [ 17794-48-8 ]
  • Downstream synthetic route of [ 17794-48-8 ]

[ 17794-48-8 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 2251-65-2 ]
  • [ 56-40-6 ]
  • [ 17794-48-8 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With sodium hydroxide In acetonitrile at 4 - 6℃; for 2.5 h;
Stage #2: With hydrogenchloride In water; acetonitrile at 0 - 6℃; for 1.5 h;
A 12-L 4-neck round bottom flask equipped with a thermocouple controller, mechanical stirrer, heating mantle, condenser and a nitrogen in/outlet adapter was charged with gycine (1, Alfa Aesar) (318 g; 4.19 mol), acetonitrile (1.2 L), and a solution of sodium hydroxide (5.31 L; 10.62 mo) and the mixture was cooled to 4° C. with stirring.
A solution of 3-(trifluoromethyl)benzoyl chloride (2, Alfa Aesar) (885.0 g; 4.12 mol) (640 mL) in acetonitrile (0.75 L) (total 1.39 L) was added dropwise over 2 h while the internal temperature was maintained between 4-6° C., and the slightly orange-pinkish solution was stirred at 4° C. for an additional 30 min.
The reaction was acidified to pH=3 with conc. 37percent HCl solution (400 mL added over 30 min) at 0-6° C., and stirred for 1 h at 0° C. (until a slightly yellowish suspension resulted).
The solid was collected by filtration, washed with cold (0° C.) deionized ("D.I") H2O (300 mL*2), dried under air-suction for 2 h, and then placed in a drying oven at 60° C. under house vacuum (120 mmHg) for 20 h to afford pure 3 as an off-white solid.
The filtrate was extracted with EtOAc (1 L*2), and the combined organic phases washed with brine (300 mL), and concentrated at 66° C. under house vacuum and then high vacuum (20 mmHg) to give crude product as an off-white waxy solid, which was triturated and sonicated with toluene (1 L) and stirred at 10° C. for 1 h.
The resulting solid was collected by filtration, washed with hexanes (50 mL*2), dried in an vacuum oven at 50° C. under house vacuum to afford additional pure title compound, 3, as an off-white solid.
The structure of 3 was confirmed with its 1H-NMR.
91% With hydrogenchloride; sodium hydroxide In acetonitrile at 0 - 3℃; for 1 h; Manufacturing example 1: (3-trifluoromethylbenzoylamino)-acetic acid [Show Image] Glycine 0.763 g (10.16 mmol) were suspended in acetonitrile 20 ml and 2 M NaOH aqueous solution 12.7 ml (25.40 mmol, 2.5 eq.) were also added. After chilling at 0-3°C, 2.12 g (10.16 mmol, 1.0 eq.) of 3- (trifluoromethyl) -benzoyl chloride were diluted with 4 ml acetonitrile and added dropwise slowly to reaction mixture. After one hour agitation at the same temperature, pH was controlled to 2 to 3 with 3N hydrochloric acid aqueous solution. After keeping upright at room temperature, upper organic solution was separated, and lower aqueous solution was extracted with ethylacetate three times. Those organic solutions obtained as described above were brought all together, dried with anhydrous magnesium sulfate and concentrated, removing the solvent under decompression. Residues were solidified with toluene, filtered, washed with normal hexane and 2.28 g (91percent) target compound as white solid were yielded. 1H NMR(400MHz,DMSO-d6) 3.94(2H,d), 7.74(1H,t), 7.93(1H,d), 8.16(1H,d), 8.20(1H,s), 9.12(1H,t)
91% With hydrogenchloride; sodium hydroxide In water; acetonitrile at 0 - 3℃; for 1 h; Manufacturing Example 1
(3-trifluoromethylbenzoylamino)-acetic acid
Glycine 0.763 g (10.16 mmol) was suspended into acetonitrile 20 ml and 2M NaOH aqueous solution 12.7 ml (25.40 mmol, 2.5 eq.) was also added.
After chilling at 0-3° C., 2.12 g (10.16 mmol, 1.0 eq.) of 3-(trifluoromethyl)-benzoyl chloride was diluted with 4 ml acetonitrile and was added dropwise slowly to reaction mixture.
After one hour agitation at same temperature, pH was controlled to 2 to 3 with 3N hydrochloric acid aqueous solution.
After keeping upright at room temperature, upper organic solution was separated, and lower aqueous solution was extracted with ethylacetate three times.
Those organic solution obtained as above was brought all together, dried with anhydrous magnesium sulfate and concentrated removing its solvent under decompression.
Residues was solidified with tolene, filtered, washed with normal hexane and 2.28 g (91percent) target compound as white solid was yielded.
1H NMR (400 MHz, DMSO-d6) 3.94 (2H, d), 7.74 (1H, t), 7.93 (1H, d), 8.16 (1H, d), 8.20 (1H, s), 9.12 (1H, t)
90%
Stage #1: With sodium hydroxide In water; acetonitrile at 0℃; for 1 h;
Stage #2: With hydrogenchloride In water; acetonitrile
(3-Trifluoromethyl-benzoylamino)acetic acid. To a rapid stirring solution of glycine (15.014 g, 0.20 mol) in MeCN (400 mL) and 2 M NaOH (250 mL) at 0° C. was slowly added a solution of 3-(trifluoromethyl)-benzoyl chloride (41.714 g, 0.20 mol) in 75 mL of MeCN over 30 min. The cloudy yellow solution was stirred at 0° C. for 30 min. The reaction mixture was acidified with 3 M HCl to pH=3, followed by removal of MeCN on rotary evaporator. The resulting mixture was then extracted with EtOAc (400 mL.x.3). The combined organic layers were dried, filtered and concentrated to give a light yellow solid (48.53 g), which was triturated with toluene (500 mL). After filtration, the solid product was washed with cold toluene until the filtrate was colorless. After dried under high vacuum over the weekend, a white powder product: 44.60 g (90percent) was afforded. MS (M+H+)=248.1. 1H NMR (DMSO-d6) δ 12.70 (br s, 1 H), 9.17 (m, 1H), 8.20 (dd, 2H), 7.94 (dd, 1H), 7.78 (m, 1H), 3.97 (d, 2H).
90%
Stage #1: With sodium hydroxide In water; acetonitrile at 0℃; for 1 h;
Stage #2: With hydrogenchloride In water; acetonitrile
Step A(3-Trifluoromethyl-benzoylamino)acetic acid. To a rapid stirring solution of glycine (15.014 g, 0.20 mol) in MeCN (400 mL) and 2 M NaOH (250 mL) at 0 °C was slowly added a solution of 3-(trifluoromethyl)-benzoyl chloride (41.714 g, 0.20 mol) in 75 mL of MeCN over 30 min. The cloudy yellow solution was stirred at 0 °C for 30 min. The reaction mixture was acidified with 3 M HCI to pH = 3, followed by removal of MeCN on rotary evaporator. The resulting mixture was then extracted with EtOAc (400 mL x 3). The combined organic layers were dried, filtered and concentrated to give a light yellow solid (48.53 g), which was triturated with toluene (500 mL). After filtration, the solid product was washed with cold toluene until the filtrate was colorless. After dried under high vacuum over the weekend, a white powder product: 44.60 g (90percent) was afforded. MS (M+H+) = 248.1. 1H NMR (DMSO-d6) δ 12.70 (br s, 1 H), 9.17 (m, 1 H), 8.20 (dd, 2H), 7.94 (dd, 1 H), 7.78 (m, 1 H), 3.97 (d, 2H).

Reference: [1] Patent: US2010/144695, 2010, A1, . Location in patent: Page/Page column 61-62
[2] Patent: EP2452939, 2012, A2, . Location in patent: Page/Page column 17
[3] Patent: US2012/190689, 2012, A1, . Location in patent: Page/Page column 11-12
[4] Patent: US2005/192302, 2005, A1, . Location in patent: Page/Page column 21
[5] Patent: WO2012/114223, 2012, A1, . Location in patent: Page/Page column 36
[6] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 37 - 41
[7] Patent: US4904680, 1990, A,
[8] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 7, p. 2099 - 2102
[9] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7473 - 7478
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