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[ CAS No. 383-70-0 ] {[proInfo.proName]}

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Chemical Structure| 383-70-0
Chemical Structure| 383-70-0
Structure of 383-70-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 383-70-0 ]

CAS No. :383-70-0 MDL No. :MFCD00029784
Formula : C4H4F3NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :IFAXXCBMQJNCCF-UHFFFAOYSA-N
M.W : 171.07 Pubchem ID :136227
Synonyms :

Calculated chemistry of [ 383-70-0 ]

Physicochemical Properties

Num. heavy atoms : 11
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 : 26.31
TPSA : 66.4 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) : -7.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.84
Log Po/w (XLOGP3) : 0.25
Log Po/w (WLOGP) : 1.01
Log Po/w (MLOGP) : -0.35
Log Po/w (SILICOS-IT) : 0.21
Consensus Log Po/w : 0.39

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -0.79
Solubility : 27.5 mg/ml ; 0.161 mol/l
Class : Very soluble
Log S (Ali) : -1.21
Solubility : 10.7 mg/ml ; 0.0624 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.54
Solubility : 49.3 mg/ml ; 0.288 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.29

Safety of [ 383-70-0 ]

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 [ 383-70-0 ]

* 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 [ 383-70-0 ]
  • Downstream synthetic route of [ 383-70-0 ]

[ 383-70-0 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 383-63-1 ]
  • [ 56-40-6 ]
  • [ 383-70-0 ]
YieldReaction ConditionsOperation in experiment
85% With triethylamine In methanol at 20℃; for 24 h; General procedure: The TFA-α-amino acid was prepared with reported procedure [1,2] with slightly modification.Triethylamine (33 mmol, 1.5 equiv.) was added to a solution of α-amino acid (22 mmol) inMeOH (22 mL). After 5 min, ethyl trifluoroacetate (29 mmol, 1.3 equiv.) was added and thereaction was allowed to stir for 24 h. The solvent was removed by rotary evaporation and theresidue that remained was dissolved in H2O (35 mL) and acidified with concentrated HCl (4 mL).After stirring for 15 min, the mixture was extracted with ethyl acetate and the organic layerswere combined and washed with brine, dried by MgSO4, filtered, and concentrated by rotaryevaporation. Further subjection into high vacuum for overnight, if needed to solidify the product(L-/D-1a–L-/D-2a, 3a, L-/D-4a–L-/D-8a).
Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 30, p. 8298 - 8309
[2] Organic Letters, 2018, vol. 20, # 18, p. 5877 - 5880
[3] Molecules, 2017, vol. 22, # 10,
[4] European Journal of Organic Chemistry, 2012, # 29, p. 5774 - 5788,15
[5] European Journal of Organic Chemistry, 2012, # 29, p. 5774 - 5788
[6] Angewandte Chemie - International Edition, 2009, vol. 48, # 11, p. 1995 - 1997
[7] European Journal of Organic Chemistry, 2009, # 28, p. 4882 - 4892
[8] Patent: WO2015/63020, 2015, A1, . Location in patent: Page/Page column 38
[9] Chemical Communications, 2018, vol. 54, # 43, p. 5410 - 5413
  • 2
  • [ 56-40-6 ]
  • [ 407-25-0 ]
  • [ 383-70-0 ]
YieldReaction ConditionsOperation in experiment
81% at 0 - 70℃; for 2 h; Large scale To a 30 L reactor equipped with a mechanical stirrer, a thermometer,a reflux condenser, an addition funnel, and nitrogeninlet-outlet was charged TFA (2 L), glycine 16 (2.0 kg, 26.6 mol)with stirring while keeping the inner temperature below 0 Cresulting in a suspension. Then to the suspension was added dropwiseTFAA (6.6 kg, 31.4 mol) with stirring while keeping the innertemperature below 70 C. After addition, the reaction mixture waskept at 70 C and stirred for another 2 h until all solid was dissolved.Completion was demonstrated by disappearance of thestarting material by HPLC after 2 h. The mixture was concentratedto dryness under vacuum at 50 C to obtain the crude 17 as a lightyellow solid. The crude material was purified by re-crystallizationfrom EtOAc (6 L) and heptane (12 L) to afford pure 17 (3.7 kg, 81percent)as a white solid: mp 120–121 C. 1H NMR (400 MHz, D2O) d 4.01 (s,2 H). 13C NMR (101 MHz, D2O) d 40.86, 117.08, 159.37, 171.66;HRMS (ESI) [C4H4F3NO3H]) calcd 170.0065, found 170.0044.
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 1355 - 1362
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2452 - 2458
[3] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 4, p. 957 - 969
[4] European Journal of Organic Chemistry, 2014, vol. 2014, # 13, p. 2664 - 2667
[5] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 4, p. 1764 - 1774
[6] Chemische Berichte, 1954, vol. 87, p. 248,256
[7] Angewandte Chemie, 1952, vol. 64, p. 136
[8] Journal of Biological Chemistry, 1954, vol. 210, p. 227,230
[9] Journal of the American Chemical Society, 1972, vol. 94, # 1, p. 265 - 268
  • 3
  • [ 431-47-0 ]
  • [ 56-40-6 ]
  • [ 383-70-0 ]
YieldReaction ConditionsOperation in experiment
87% With triethylamine In methanol for 18 h; Methyl trifluoroacetate (804 μL, 7.99 mmoles) and triethylamine (928 μL, 6.66 mmoles) were added to a suspension of glycine (500 mg, 6.66 mmoles) in methanol (2.5 mL). After the mixture was stirred vigorously for 18 h, 1 N HCl was added dropwise until the a pH of 2 was obtained. The reaction was added to ethyl acetate (30 mL) was washed with 1 N HCl (2 x 10 mL), dried over MgSO4, and concentrated in vacuo to yield the amide as a white solid (991 mg, 5.79 mmoles, 87percent). LRMS: (CI+) calcd for C4H4NO3F3 (M + NH4): 189; found: 189. 1H NMR: spectrum is consistent with the predicted structure.
Reference: [1] Russian Journal of General Chemistry, 1994, vol. 64, # 5.2, p. 791 - 792[2] Zhurnal Obshchei Khimii, 1994, vol. 64, # 5, p. 878
[3] Patent: EP1235851, 2006, B1, . Location in patent: Page/Page column 46
[4] Synthesis, 1976, p. 399 - 401
  • 4
  • [ 56-40-6 ]
  • [ 383-70-0 ]
Reference: [1] Patent: US6191150, 2001, B1,
[2] Patent: US2014/100217, 2014, A1, . Location in patent: Page/Page column
  • 5
  • [ 848860-95-7 ]
  • [ 56-40-6 ]
  • [ 383-70-0 ]
Reference: [1] Synlett, 2005, # 2, p. 255 - 258
  • 6
  • [ 383-64-2 ]
  • [ 56-40-6 ]
  • [ 383-70-0 ]
Reference: [1] Journal of the American Chemical Society, 1955, vol. 77, p. 2779,2782
  • 7
  • [ 500-73-2 ]
  • [ 56-40-6 ]
  • [ 383-70-0 ]
Reference: [1] Chemische Berichte, 1959, vol. 92, p. 2095,2098
  • 8
  • [ 354-32-5 ]
  • [ 56-40-6 ]
  • [ 383-70-0 ]
Reference: [1] Journal of Pharmaceutical Sciences, 1979, vol. 68, # 4, p. 496 - 499
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