Home Cart 0 Sign in  
X

[ CAS No. 614-75-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 614-75-5
Chemical Structure| 614-75-5
Chemical Structure| 614-75-5
Structure of 614-75-5 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 614-75-5 ]

Related Doc. of [ 614-75-5 ]

Alternatived Products of [ 614-75-5 ]

Product Details of [ 614-75-5 ]

CAS No. :614-75-5 MDL No. :MFCD00004323
Formula : C8H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :CCVYRRGZDBSHFU-UHFFFAOYSA-N
M.W : 152.15 Pubchem ID :11970
Synonyms :

Calculated chemistry of [ 614-75-5 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.01
TPSA : 57.53 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) : -6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.9
Log Po/w (XLOGP3) : 0.85
Log Po/w (WLOGP) : 1.02
Log Po/w (MLOGP) : 1.05
Log Po/w (SILICOS-IT) : 1.06
Consensus Log Po/w : 0.98

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 : 3.91 mg/ml ; 0.0257 mol/l
Class : Very soluble
Log S (Ali) : -1.64
Solubility : 3.47 mg/ml ; 0.0228 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.58
Solubility : 3.97 mg/ml ; 0.0261 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.18

Safety of [ 614-75-5 ]

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

Application In Synthesis of [ 614-75-5 ]

* 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 [ 614-75-5 ]
  • Downstream synthetic route of [ 614-75-5 ]

[ 614-75-5 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 103-82-2 ]
  • [ 156-38-7 ]
  • [ 621-37-4 ]
  • [ 614-75-5 ]
Reference: [1] Tetrahedron Letters, 1983, vol. 24, # 44, p. 4847 - 4850
[2] Tetrahedron Letters, 1983, vol. 24, # 44, p. 4847 - 4850
[3] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 1, p. 148 - 152
  • 2
  • [ 103-82-2 ]
  • [ 156-38-7 ]
  • [ 621-37-4 ]
  • [ 451-13-8 ]
  • [ 64700-73-8 ]
  • [ 614-75-5 ]
Reference: [1] Agricultural and Biological Chemistry, 1987, vol. 51, # 3, p. 947 - 948
  • 3
  • [ 614-75-5 ]
  • [ 74-88-4 ]
  • [ 27798-60-3 ]
YieldReaction ConditionsOperation in experiment
94% With potassium carbonate In acetonitrile for 15 h; Heating / reflux Example 9:; (2-Methoxy-phenyl) -acetic acid methyl ester; A solution of methyl iodide (188 g, 1.33 mole) in acetonitrile (200 mL) was slowly added to a mixture of (2-hydroxy-phenyl) -acetic acid (80 g, 0.53 mol) and potassium carbonate (254 g, 1.84 mol) in acetonitrile (800 mL) under reflux. The reaction was heated to reflux for 15 hours. The reaction mixture was cooled and the precipitate was removed by filtration. The filtrate was evaporated to dryness to give the crude product (90. g, 0.50 mol, 94 percent)
89% With potassium carbonate In acetone at 20℃; for 12 h; To a stirred solution of 2-hydroxyphenylacetic acid (1.04 g, 6.8 mmol) in acetone (30 mL), K2CO3 (2.83 g, 20.5 mmol) and MeI (1.06 mL, 17.1 mmol) was added. The mixture was stirred at room temperature for 12 h and then acetone was removed at vacuum. Water (20 mL) was added to the mixture and extracted with ethyl acetate (2*30 mL). The organic layer was washed with water (2*20 mL), brine (20 mL), dried (Na2SO4) and concentrated. The crude product was purified by silica gel column chromatography to get 16 (1.10 g, 89percent) as colorless oil. Rf 0.5 (1:20 ethyl acetate:hexane); 1H NMR (CDCl3, 500 MHz) δ 7.24 (d, 1H, J=8.0Hz, C6′-H), 7.16 (d, 1H, J=8.0Hz, C3′-H), 6.92–6.85 (m, 2H, C4′-H & C5′-H), 3.80 (s, OCH3), 3.67 (s, 3H, CO2CH3), 3.62 (s, 2H, C2-H2).
Reference: [1] Patent: WO2005/75435, 2005, A1, . Location in patent: Page/Page column 138-139
[2] Tetrahedron, 2016, vol. 72, # 23, p. 3324 - 3334
  • 4
  • [ 584-08-7 ]
  • [ 614-75-5 ]
  • [ 74-88-4 ]
  • [ 27798-60-3 ]
Reference: [1] Patent: US5656629, 1997, A,
  • 5
  • [ 67-56-1 ]
  • [ 614-75-5 ]
  • [ 22446-37-3 ]
YieldReaction ConditionsOperation in experiment
95% at 20℃; for 2 h; PREPARATION lA: methyl 2-(2-hydroxyphenyl)acetate: [0194] To a solution of 2-(2-hydroxyphenyl)acetic acid (400 g, 2.63 mmol) in MeOH (3.0 L) was bubbled with HCl (g) at room temperature for 2 hours. The resulting mixture was concentrated, dried under vacuo to give compound 1A (415 g, yield 95percent) as yellow oil, and the oil was solidified after standing overnight. [0195] JH NMR (CDCI3, 400 MHz): δ 7.20-7.16 (m, 1H), 7.11-7.09 (m, 1H), 6.93-6.86 (m, 2H), 4.48 (br s, 1H), 3.74 (s, 2H), 3.69 (s, 3H).
90% With hydrogenchloride In waterReflux To a solution of compound 45 (2.0 g, 13.2mmol) in MeOH (30m1) was added HC1 solution (0.2 ml, 3 5percent), and the resulting mixture was heated under reflux overnight. Then themixture was concentrated, and the residue was dissolved in ethyl acetate (50 ml), and washed with NaHCO3, brine successively. The organic layer was dried over anhydrous Na2504, then filtered and concentrated, and the pale yellow solid was used for next step without further purification (yield 90percent). ‘HNMR(400 MHz, CDC13): 7.36 (s, 1H), 7.23 (t, J= 7.6 Hz, 1H), 7.12 (d, J= 8.0 Hz, 1H), 6.97 (d, J= 8.0 Hz, 1H), 6.91 (td, J= 7.6, 1.0 Hz, 1H), 3.78 (s,3H), 3.71 (s, 2H).
87% at 20℃; for 18 h; [00121] A solution of 2-(2-hydroxyphenyl)acetic acid (3.00 g, 19.7 mmol) in methanol (40 mL) was treated with sulfuric acid (0.95 mL, 17.8 mmol) and the reaction was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate (250 mL), and the solution was washed with water (2 x 150 mL) and with saturated aqueous sodium chloride (150 mL); dried over sodium sulfate; filtered and evaporated in vacuo to give the crude product. Recrystallization from hot hexanes gave methyl 2-(2-hydroxyphenyl)acetate (2.83 g, 87percent). 1H NMR (400 MHz, CDCI3): 5 7.20 (ddd, J = 7.7, 7.4, 1.8 Hz, I H), 7.09-7.11 (m, 1 H), 6.94 (dd, J = 8.0, 1.2 Hz, 1 H), 6.88 (ddd, J = 7.4, 7.4, 1.2 Hz, 1 H), 3.75 (s, 3H), 3.69 (s, 2H).
87% at 20℃; for 18 h; A solution of 2-(2-hydroxyphenyl)acetic acid (3.00 g, 19.7 mmol) in methanol (40 mL) was treated with sulfuric acid (0.95 mL, 17.8 mmol) and the reaction was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate (250 mL), and the solution was washed with water (2 x 150 mL) and with saturated aqueous sodium chloride (150 mL); dried over sodium sulfate; filtered and evaporated in vacuo to give the crude product. Recrystallization from hot hexanes gave methyl 2-(2-hydroxyphenyl)acetate (2.83 g, 87percent). 1H NMR (400 MHz, CDCI3): δ 7.20 (ddd, J = 7.7, 7.4, 1.8 Hz, 1 H), 7.09-7.11 (m, 1 H), 6.94 (dd, J = 8.0, 1.2 Hz, 1 H), 6.88 (ddd, J = 7.4, 7.4, 1.2 Hz, 1 H), 3.75 (s, 3H), 3.69 (s, 2H).
2.8 g for 10 h; Reflux Preparation Example 4 Synthesis of (methyl 2-methoxymethoxy phenyl) acetate (0096) 3.04 g (20.0 mmol) of 2-hydroxyphenyl acetic acid was dissolved in 20 ml of methanol, and 1.0 ml of concentrated sulfuric acid was added thereto. The reaction solution was refluxed for 10 hours, and then distilled under reduced pressure for concentration. The concentrate was subjected to column chromatography to obtain 2.78 g (16.7 mmol) of (methyl 2-hydroxyphenyl) acetate. 2.8 g (20.0 mmol) of K2CO3 was again added to a solution obtained by dissolving the aforementioned compound in 20 ml of acetone, 2.40 g (30.0 mmol) of chloromethyl methyl ether was slowly added thereto for 30 minutes while the resulting solution was vigorously stirred at room temperature, and the mixture was vigorously stirred overnight. Then, the reaction solution was filtered to remove solid ingredients, the filtrate was distilled under reduced pressure for concentration, and then the concentrate was purified by silica gel column chromatography to obtain 2.56 g (12.3 mmol) of (2-methoxymethoxy phenyl) acetic methyl ester. (0097) 1H-NMR (CDCl3): 7.239 (t, 1H, J=8.0 Hz), 7.201 (d, 1H, J=8.0 Hz), 7.099 (d, 1H, J=8.0 Hz), 6.973 (t, 1H, J=8.0 Hz), 5.191 (s, 2H), 3.687 (s, 3H), 3.666 (s, 2H), 3.459 (s, 3H).

Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 31, p. 5147 - 5155
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8948 - 8952
[3] Organic Letters, 2008, vol. 10, # 18, p. 3969 - 3972
[4] Patent: WO2015/102990, 2015, A1, . Location in patent: Paragraph 0193-0195
[5] Journal of Organic Chemistry, 1994, vol. 59, # 1, p. 203 - 213
[6] European Journal of Medicinal Chemistry, 2009, vol. 44, # 4, p. 1779 - 1787
[7] Journal of Chemical Crystallography, 2009, vol. 39, # 12, p. 927 - 930
[8] Patent: WO2018/93924, 2018, A1, . Location in patent: Paragraph 0313; 0314
[9] Patent: WO2016/54728, 2016, A1, . Location in patent: Paragraph 00121
[10] Patent: WO2016/74068, 2016, A1, . Location in patent: Paragraph 00115
[11] Journal of Medicinal Chemistry, 2017, vol. 60, # 1, p. 441 - 457
[12] Journal of the American Chemical Society, 1948, vol. 70, p. 1930
[13] Journal of the American Chemical Society, 1976, vol. 98, p. 3555 - 3564
[14] Journal of Medicinal Chemistry, 1968, vol. 11, p. 611 - 612
[15] Patent: WO2010/129379, 2010, A1, . Location in patent: Page/Page column 134
[16] Patent: WO2015/191616, 2015, A1, . Location in patent: Paragraph 0290
[17] Patent: JP5690514, 2015, B2, . Location in patent: Paragraph 0068
[18] Patent: TW2016/7949, 2016, A, . Location in patent: Paragraph 0066
[19] Patent: US2016/272650, 2016, A1, . Location in patent: Paragraph 0096-0097
[20] Patent: CN106380397, 2017, A, . Location in patent: Paragraph 0019; 0020; 0023; 0024; 0027; 0028; 0031; 0032
  • 6
  • [ 614-75-5 ]
  • [ 22446-37-3 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogenchloride In methanol Step 1
(2-hydroxy-phenyl)-acetic acid methyl ester
To a solution of 2-hydroxyphenylacetic acid (20.0 g, 129.7 mmol) in 250 mL of methanol was bubbled at room temperature anhydrous hydrochloric acid for 5 minutes.
The reaction was capped and stirred overnight.
The reaction was then concentrated under reduced pressure to yield a pale oil (20.5 g, 95percent).
1 H NMR (300 MHz, DMSO): δ 9.45 (s, 1H), 7.15 (m, 2H), 6.75 (m, 2H), 3.57 (d, 2H), 3.35 (s, 3H).
80% With sulfuric acid In methanol; silica gel; toluene (a)
Methyl (2-Hydroxyphenyl)acetate
A solution of 15 gm (0.1 mole) of 2-hydroxyphenylacetic acid in 500 ml methanol and 2 ml concentrated sulfuric acid was placed in a Soxhlet extractor charged with 3 A molecular sieves.
The solution was heated to reflux for 72 hours, and the sieves were exchanged at 24-hour intervals.
The reaction medium was then evaporated to an oil which was dissolved in 100 ml toluene and extracted with 3*100 ml portions of water.
The toluene phase was dried over magnesium sulfate, treated with activated charcoal and evaporated to provide 13 gm (80percent yield) of a yellow oil.
The NMR spectrum was consistent with the assigned structure and this material was used in the next reaction step.
Reference: [1] Patent: US5922697, 1999, A,
[2] Patent: US4623652, 1986, A,
  • 7
  • [ 75-36-5 ]
  • [ 614-75-5 ]
  • [ 22446-37-3 ]
YieldReaction ConditionsOperation in experiment
92% With hydrogenchloride; sodium hydrogencarbonate In methanol EXAMPLE 3
This Example illustrates the preparation of (E)-methyl 2-[2'-(5"-nitropyridin-2"-yloxy)phenyl]-3-methoxyacrylate (Compound No. 133 of Table I).
2-(Hydroxyphenyl)acetic acid (50 g) was added to a solution of hydrogen chloride in methanol [prepared from acetyl chloride (25 ml) and methanol (250 ml)].
The solution was stirred at room temperature for three hours and then allowed to stand overnight (fifteen hours).
The resulting mixture was concentrated under reduced pressure, and the residue was taken up in ether (250 ml) and washed with an aqueous solution of sodium bicarbonate until effervescence ceased.
The ethereal solution was dried and then concentrated under reduced pressure and the resulting solid was recrystallized from ether/petrol to afford methyl (2-hydroxyphenyl)acetate (50 g; 92percent yield) as white, powdery crystals, mp. 70°-72° C.; infrared max. (nujol mull): 3420, 1715 cm-1; 1 H nmr (90 MHz); delta 3.70 (2H,s), 3.75 (3H,s), 6.80-6.95 (2H,m), 7.05-7.10 (1H,m), 7.15-7.25 (1H,m), 7.40 (1H,s)ppm.
Reference: [1] Patent: US5057146, 1991, A,
[2] Tetrahedron Letters, 2013, vol. 54, # 37, p. 5052 - 5055
  • 8
  • [ 75-36-5 ]
  • [ 614-75-5 ]
  • [ 22446-37-3 ]
YieldReaction ConditionsOperation in experiment
92% With hydrogenchloride; sodium hydrogencarbonate In methanol EXAMPLE 1
This Example illustrates the preparation of E-methyl 3-methoxy-2-[2'-(benzoxazol-2"-yloxyphenyl)]propenoate (Compound No. 44 of Table I).
2-Hydroxyphenylacetic acid (50 g) was added to a solution of hydrogen chloride in methanol [prepared from acetyl chloride (25 ml) and methanol (250 ml)].
The solution was stirred at room temperature for three hours and then allowed to stand overnight (fifteen hours).
The resulting mixture was concentrated under reduced pressure, and the residue was taken up in ether (250 ml) and washed with an aqueous solution of sodium bicarbonate until effervescence ceased.
The ethereal solution was dried and then concentrated under reduced pressure and the resulting solid was recrystallized from ether/petrol to afford methyl 2-hydroxyphenylacetate (50 g; 92percent yield) as white, powdery crystals, M.P. 70°-72° C.; infrared maxima (nujol mull): 3420, 1715 cm-1; 1 H nmr (CDCl3, 90 MHz): delta 3.70 (2H, s), 3.75 (3H,s), 6.80-6.95 (2H,m), 7.05-7.10 (1H,m), 7.15-7.25 (1H,m), 7.40 (1H,s)ppm.
Reference: [1] Patent: US5374644, 1994, A,
  • 9
  • [ 75-36-5 ]
  • [ 614-75-5 ]
  • [ 22446-37-3 ]
YieldReaction ConditionsOperation in experiment
92% With hydrogenchloride; sodium hydrogencarbonate In methanol EXAMPLE 1
This Example illustrates the preparation of E-methyl 2-[2'-(6"-chloropyrazin-2"-yloxy)phenyl]-3-methoxypropenoate (Compound No. 2 of Table I).
2-Hydroxyphenylacetic acid (50 g) was added to a solution of hydrogen chloride in methanol [prepared from acetyl chloride (25 ml) and methanol (250 ml)].
The solution was stirred at room temperature for three hours and then allowed to stand overnight (fifteen hours).
The resulting mixture was concentrated under reduced pressure, and the residue was taken up in ether (250 ml) and washed with an aqueous solution of sodium bicarbonate until effervescence ceased.
The ethereal solution was dried and then concentrated under reduced pressure and the resulting solid was recrystallized from ether/petrol to afford methyl 2-hydroxyphenylacetate (50 g; 92percent YIELD) as white, powdery crystals, M.P. 70°-72° C.; infrared maxima (nujol mull): 3420, 1715 cm-1; 1 H nmr (CDCl3, 90 MHz): delta 3.70 (2H, s), 3.75 (3H, s), 6.80-6.95 (2H, m), 7.05-7.10 (1H, m), 7.15-7.25 (1H, m), 7.40 (1H, s) ppm.
Reference: [1] Patent: US4870075, 1989, A,
  • 10
  • [ 7440-44-0 ]
  • [ 614-75-5 ]
  • [ 22446-37-3 ]
Reference: [1] Patent: US4695648, 1987, A,
  • 11
  • [ 67-56-1 ]
  • [ 614-75-5 ]
  • [ 22446-37-3 ]
  • [ 155388-58-2 ]
Reference: [1] Journal of the Chinese Chemical Society, 2005, vol. 52, # 1, p. 173 - 180
  • 12
  • [ 186581-53-3 ]
  • [ 614-75-5 ]
  • [ 22446-37-3 ]
Reference: [1] Takeda Kenkyusho Nenpo, 1951, vol. 10, p. 10,13[2] Chem.Abstr., 1953, p. 4860
  • 13
  • [ 614-75-5 ]
  • [ 40525-65-3 ]
Reference: [1] Patent: JP5690514, 2015, B2,
  • 14
  • [ 67-56-1 ]
  • [ 614-75-5 ]
  • [ 220801-66-1 ]
YieldReaction ConditionsOperation in experiment
94% at 20℃; for 18 h; 2-(2-hydroxyphenyl)acetic acid (484 g, 3.18 mol) was dissolved in methanol, and then tetrabutylammonium tribromide (1549 g, 3.18 mol) was added to the solution. The resulting mixture was allowed to stir at room temperature for 18 hours. After evaporation of solvent in vacuo, the residue obtained was dissolved in EtOAc. The organic layer was washed with 1 N HC1, water and brine, dried and concentrated, the residue obtained was purified using flash column chromatography on silica gel (eluted with PE / EtOAc = 10 / 1) to give pure methyl 2-(5-bromo-2-hydroxyphenyl)acetate (750 g, 94percent). 1H- MR (400 MHz, CDC13) δ 7.48 (br s, 1H), 7.20-7.25 (m, 2H), 6.75-6.78 (m, 1H), 3.74 (s, 3H), 3.62 (s, 2H). MS (M+H)+: 245.
90% at 20℃; for 18 h; 2-(2-hydroxyphenyl)acetic acid (100 g, 0.66 mol) was dissolved in MeOH, and then TBATB (320 g, 0.66 mmol) was added to the solution. The resulting mixture was stirred at RT for 18 hours. After evaporation of solvent, the residue was dissolved in diethyl ether. The organic layer was washed with 1 N HC1, 2 M sodium bisulfate, H20 and brine, dried and evaporated to yield methyl 2-(5-bromo-2-hydroxyphenyl)acetate (145 g, yield: 90percent) 1H-NMR (400 MHz, CDCl3) δ 7.48 (br s, 1H), 7.20-7.25 (m, 2H), 6.75-6.78 (m, 1H), 3.74 (s, 3H), 3.62 (s, 2H). MS (M+H)+: 245.
Reference: [1] Patent: WO2011/106986, 2011, A1, . Location in patent: Page/Page column 38; 39
[2] Patent: WO2011/106929, 2011, A1, . Location in patent: Page/Page column 79
[3] ChemMedChem, 2017, vol. 12, # 17, p. 1436 - 1448
[4] Journal of Medicinal Chemistry, 1999, vol. 42, # 1, p. 164 - 172
[5] Patent: WO2013/134562, 2013, A1, . Location in patent: Paragraph 00109
[6] Patent: WO2014/99503, 2014, A1, . Location in patent: Paragraph 00104
[7] Patent: WO2015/35059, 2015, A1, . Location in patent: Paragraph 00105
[8] Bioorganic and Medicinal Chemistry Letters, 2018,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 614-75-5 ]

Aryls

Chemical Structure| 102-32-9

[ 102-32-9 ]

3,4-Dihydroxyphenylacetic acid

Similarity: 0.95

Chemical Structure| 621-37-4

[ 621-37-4 ]

3-Hydroxyphenylacetic acid

Similarity: 0.95

Chemical Structure| 93-25-4

[ 93-25-4 ]

2-Methoxyphenylacetic acid

Similarity: 0.93

Chemical Structure| 22446-37-3

[ 22446-37-3 ]

Methyl 2-(2-hydroxyphenyl)acetate

Similarity: 0.91

Chemical Structure| 1798-09-0

[ 1798-09-0 ]

3-Methoxyphenylacetic acid

Similarity: 0.90

Carboxylic Acids

Chemical Structure| 102-32-9

[ 102-32-9 ]

3,4-Dihydroxyphenylacetic acid

Similarity: 0.95

Chemical Structure| 621-37-4

[ 621-37-4 ]

3-Hydroxyphenylacetic acid

Similarity: 0.95

Chemical Structure| 93-25-4

[ 93-25-4 ]

2-Methoxyphenylacetic acid

Similarity: 0.93

Chemical Structure| 29913-51-7

[ 29913-51-7 ]

2-(4-Hydroxyphenyl)-2-methylpropanoic acid

Similarity: 0.90

Chemical Structure| 1798-09-0

[ 1798-09-0 ]

3-Methoxyphenylacetic acid

Similarity: 0.90