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Chemical Structure| 18699-02-0
Chemical Structure| 18699-02-0
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Product Details of [ 18699-02-0 ]

CAS No. :18699-02-0 MDL No. :MFCD00196165
Formula : C10H11NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :MROJXXOCABQVEF-UHFFFAOYSA-N
M.W : 193.20 Pubchem ID :2018
Synonyms :
4-Acetylaminophenylacetic Acid;NSC 170317;MS-932

Calculated chemistry of [ 18699-02-0 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 52.3
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) : -6.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.22
Log Po/w (XLOGP3) : 0.8
Log Po/w (WLOGP) : 1.08
Log Po/w (MLOGP) : 1.14
Log Po/w (SILICOS-IT) : 1.15
Consensus Log Po/w : 1.08

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.59
Solubility : 4.91 mg/ml ; 0.0254 mol/l
Class : Very soluble
Log S (Ali) : -1.78
Solubility : 3.24 mg/ml ; 0.0168 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.57
Solubility : 0.524 mg/ml ; 0.00271 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.2

Safety of [ 18699-02-0 ]

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 [ 18699-02-0 ]

* 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 [ 18699-02-0 ]
  • Downstream synthetic route of [ 18699-02-0 ]

[ 18699-02-0 ] Synthesis Path-Upstream   1~13

  • 1
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YieldReaction ConditionsOperation in experiment
99% at 20℃; Cooling with ice p-Aminophenylacetic acid (1.02 mmol) (manufactured by Wako Pure Chemical Industries) was dissolved indichloromethane-methanol-water (1:3:1, 50 ml), and acetic anhydride (2.12 mmol) was added thereto under ice-cooling,followed by stirring overnight while gradually returning to room temperature. The solvent was evaporated under reducedpressure to give the titled compound (196.4 mg, yield 99percent). The structure was identified by 1H-NMR1H-NMR (500 MHz,CD3OD) d (ppm) = 2.11 (3H, s, Ac), 3.55 (2H, s, Ph-CH2-), 7.21-7.49 (4H, m, Aromatic H)
46% With triethylamine In dichloromethane at 20℃; for 16 h; To a stirred solution of 2-(4-aminophenyl) acetic acid (2.0 g, 13.23 mmol) and TEA (3.66 mL, 26.5 mmol) in DCM (20 mL) at RT was added acetic anhydride (1.25 1 mL, 13.23 mmol) drop wise and the reaction mixture was stirred for 16 hours at RT. The reaction mixture was acidified, diluted with DCM (30 mL) and the organic layer was washed with water (10 mL) and brine (10 mL), dried over sodium sulphate, concentrated to obtain the title compound(1.2 g, 46 percent).
41% With sodium carbonate In water; acetonitrile at 20℃; for 3 h; To a stirred solution of 4-aminophenylacetic acid (31.5 g, 0.209 mol) in acetonitrile (550 ml) was added acetic anhydride (57 ml), sodium carbonate (66.5 g, 0.627 mol) and water (55 ml). The reaction was allowed to stir at room temperature for 3 hours. Reaction mixture was then poured onto a solution of conc. HCI (130 ml) and water (1200 ml). Reaction mixture was then extracted with EtOAc (2 x 750 ml). Combined organic layers were dried over MgSO4, filtered and evaporated under reduced pressure to reveal a tan solid. Purification by column chromatography [Si02 : 100percent DCM to 10percent MeOH/DCM] afforded a light tan solid (16. 5g, 41 percent).
Reference: [1] Patent: EP3363463, 2018, A2, . Location in patent: Paragraph 0148
[2] Asian Journal of Chemistry, 2012, vol. 24, # 4, p. 1538 - 1540
[3] Journal of the American Chemical Society, 1988, vol. 110, # 7, p. 2282 - 2286
[4] Journal of the American Chemical Society, 2009, vol. 131, p. 456 - 457
[5] Patent: WO2015/145371, 2015, A1, . Location in patent: Page/Page column 40
[6] Patent: WO2005/84658, 2005, A1, . Location in patent: Page/Page column 9
[7] Chemische Berichte, 1882, vol. 15, p. 838[8] Chemische Berichte, 1882, vol. 15, p. 3060
[9] Patent: US3936467, 1976, A,
[10] Patent: US3993763, 1976, A,
[11] Patent: US2004/6056, 2004, A1, . Location in patent: Page 37
  • 2
  • [ 1197-55-3 ]
  • [ 64-19-7 ]
  • [ 18699-02-0 ]
YieldReaction ConditionsOperation in experiment
100% at 150℃; Microwave irradiation According to a reported procedure [49], 4-aminophenylaceticacid (4, 2.0 g) was added to acetic acid (20 mL) under microwave irradiation (150 °C) for 1 h. Thereaction mixture was poured into ethyl acetate then washed with water and then allowed to dry toyield the compound 8 (Scheme 9; 2.252 g; 100percent) as a white-grey solid. m.p. 166–168 °C [57]. 1H-NMR(300 MHz, DMSO-d6): δ = 9.92 (s, 1H), 7.51 (d, 3J = 8.6 Hz, 2H), 7.16 (d, 3J = 8.6 Hz, 2H), 3.49 (s, 1H),2.03 (s, 3H). 13C-NMR (75 MHz, DMSO-d6): δ = 172.79 (Cq), 172.02 (Cq), 168.13 (Cq), 137.83 (Cq), 129.52(CH), 118.87 (CH), 40.11 (CH2), 23.87 (CH3). IR: 3348 (w), 1709 (s), 1638 (m), 1601 (s), 1542 (s), 1538 (s),1221 (m), 1195 (m), 968 (w), 806 (w), 723 (w). 1H-NMR (400 MHz, CD3OD): δ 7.48 (d, J = 8.8 Hz, 2H),7.21 (d, J = 8.8 Hz, 2H), 3.55 (s, 2H), 2.10 (s, 3H); HRMS (FAB+): [M + H]+ calcd. for C10H12O3N,194.0817; found, 194.0770.
Reference: [1] Molecules, 2017, vol. 22, # 1,
[2] Synthetic Communications, 2008, vol. 38, # 7, p. 1028 - 1035
  • 3
  • [ 127-19-5 ]
  • [ 1197-55-3 ]
  • [ 18699-02-0 ]
YieldReaction ConditionsOperation in experiment
95.2% at 168℃; for 2 h; Heating mixing p-aminophenylacetic acid, N, N-dimethylacetamide and ammonium chloride, heating to 168 ° C, refluxing for 2 h, and then cooling to room temperature, Add ice water to 4 , insulation crystallization 50min, filtration, washing with ice water filter cake, adjust the temperature to 65 , vacuum drying 4.5h to be acetamidophenylacetic acid, of which p-aminophenylacetic acid, N, N-bis The weight ratio (g / ml) ratio of methylacetamide is 3:15, the weight ratio of p-aminophenylacetic acid and ammonium chloride is 3: 1.5, and the weight ratio of p-aminophenylacetic acid to ice water during crystallization is For 3: 8.
Reference: [1] Patent: CN106278925, 2017, A, . Location in patent: Paragraph 0029-0030
  • 4
  • [ 1197-55-3 ]
  • [ 108-24-7 ]
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  • [ 18699-02-0 ]
Reference: [1] Patent: WO2011/145022, 2011, A1, . Location in patent: Page/Page column 69
  • 5
  • [ 113180-61-3 ]
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Reference: [1] Journal of the American Chemical Society, 1988, vol. 110, # 7, p. 2282 - 2286
  • 6
  • [ 556-18-3 ]
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Reference: [1] Asian Journal of Chemistry, 2012, vol. 24, # 4, p. 1538 - 1540
  • 7
  • [ 97562-37-3 ]
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Reference: [1] Asian Journal of Chemistry, 2012, vol. 24, # 4, p. 1538 - 1540
  • 8
  • [ 335200-33-4 ]
  • [ 156-38-7 ]
  • [ 18699-02-0 ]
  • [ 335200-30-1 ]
Reference: [1] Chemical Communications, 2001, # 1, p. 19 - 20
  • 9
  • [ 106664-49-7 ]
  • [ 156-38-7 ]
  • [ 18699-02-0 ]
Reference: [1] Chemical Communications, 2001, # 1, p. 19 - 20
  • 10
  • [ 1197-55-3 ]
  • [ 75-36-5 ]
  • [ 18699-02-0 ]
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 6, p. 641 - 644
  • 11
  • [ 335200-29-8 ]
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  • [ 335200-30-1 ]
Reference: [1] Chemical Communications, 2001, # 1, p. 19 - 20
  • 12
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  • [ 122-85-0 ]
  • [ 103-84-4 ]
Reference: [1] Arzneimittel-Forschung/Drug Research, 2008, vol. 58, # 4, p. 182 - 187
  • 13
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Reference: [1] Arzneimittel-Forschung/Drug Research, 2008, vol. 58, # 4, p. 182 - 187
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