177429-27-5|Ethyl 4-(benzyloxy)-3-hydroxybenzoate| Ambeed

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Quality Control of [ 177429-27-5 ] Purity: 97% SDS Specification

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Product Details of [ 177429-27-5 ]

CAS No. :	177429-27-5
Formula :	C₁₆H₁₆O₄
M.W :	272.30
SMILES Code :	O=C(OCC)C1=CC=C(OCC2=CC=CC=C2)C(O)=C1
MDL No. :	MFCD26385855
InChI Key :	FAENFNUEKOZHCS-UHFFFAOYSA-N
Pubchem ID :	11311797

Safety of [ 177429-27-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 177429-27-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	20
Num. arom. heavy atoms	12
Fraction Csp3	0.19
Num. rotatable bonds	6
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	75.53
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	55.76 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.04
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.25
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.0
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.72
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.2
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.04

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.62
Solubility	0.0648 mg/ml ; 0.000238 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.09
Solubility	0.0219 mg/ml ; 0.0000804 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-4.97
Solubility	0.00294 mg/ml ; 0.0000108 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	Yes
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	Yes
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.65 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<0.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.2

Application In Synthesis of [ 177429-27-5 ]

* 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.

Downstream synthetic route of [ 177429-27-5 ]

[ 177429-27-5 ] Synthesis Path-Downstream 1~35

1
[ 3943-89-3 ]
[ 100-39-0 ]
[ 188564-63-8 ]
[ 177429-27-5 ]

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 4076 - 4078.

2
[ 17507-56-1 ]
[ 177429-27-5 ]
[ 188564-68-3 ]

References: [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 323 - 334.

3
[ 3943-89-3 ]
[ 100-39-0 ]
[ 188564-63-8 ]
[ 177429-27-5 ]
[ 174398-83-5 ]

References: [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 323 - 334.

4
[ 177429-27-5 ]
[ 623-48-3 ]
[ 188564-65-0 ]

References: [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 323 - 334.

5
4-benzyloxy-3-(4-nitro-benzyloxy)-benzoic acid ethyl ester [ No CAS ]
[ 106-49-0 ]
[ 177429-27-5 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 5965 - 5967.

6
4-Benzyloxy-3-(4-methoxycarbonyl-benzyloxy)-benzoic acid ethyl ester [ No CAS ]
[ 177429-27-5 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 5965 - 5967.

7
4-Benzyloxy-3-(3-methoxycarbonyl-benzyloxy)-benzoic acid ethyl ester [ No CAS ]
[ 177429-27-5 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 5965 - 5967.

8
[ 3943-89-3 ]
[ 100-39-0 ]
[ 177429-27-5 ]

Yield	Reaction Conditions	Operation in experiment
25%	With potassium carbonate; In acetonitrile; at 55℃; for 16h;	1-(Bromomethyl)benzene (68 g, 398 mmol, 1.05 equiv) and potassium carbonate (67 g, 485 mmol, 1.50 equiv) were added to a solution of ethyl 3,4-dihydroxybenzoate (67 g, 368 mmol, 1.00 equiv) and acetonitrile (400 mL). The resulting mixture was stirred at about 55 C. for about 16 hours. The solids were removed by filtration and the filtrate was concentrated in vacuo. The solids was purified by silica gel column chromotagraphy (dichloromethane/petroleum ether 1:10) to afford the title product as a white solid (25 g, yield 25%).
	With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20℃;	A 25 g quantity of ethyl 3, 4-dihydroxybenzoate was dissolved in 250 ml of dimethylformamide, and 5.5 g of sodium hydride was added with ice-cooling and stirring. The mixture was stirred, and a solution of 16.3 ml of benzylbromide in 10 ml of dimethylformamide was added dropwise. After the dropwise addition, the mixture was stirred at room temperature overnight. Water was added to the reaction mixture and extraction with ethyl acetate was performed. The organic layer was washed with water twice and concentrated by removing the solvent under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane : ethyl acetate = 2 : 1) to give 15 g of crude crystals. The crude crystals were recrystallized from a mixture of 30 ml of n-hexane and 15 ml of ethyl acetate to give 8.6 g of colorless plate crystalline ethyl 4-benzyloxy-3-hydroxybenzonate. 1H-NMR (CDCl3) delta: 7.67-7.47 (2H, m) , 7.41-7.30 (5H, m) , 6.94 (IH, d, J = 8.7 Hz), 5.67 (IH, s) , 5.16 (2H, s) , 4.34 (2H, q, J = 7.2 Hz), 1.37 (3H, t, J = 7.2 Hz)

References: [1]ChemMedChem,2017,vol. 12,p. 1303 - 1318.
[2]Patent: US2010/75916,2010,A1 .Location in patent: Page/Page column 17.
[3]Patent: WO2007/58338,2007,A2 .Location in patent: Page/Page column 64.

9
[ 177429-27-5 ]
2-[5-Carboxy-3-(carboxy-phosphono-methoxy)-2-hydroxy-phenyl]-2-hydroxy-malonic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 323 - 334.

10
[ 177429-27-5 ]
[ 188564-66-1 ]

References: [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 323 - 334.

11
[ 177429-27-5 ]
[ 188564-69-4 ]

References: [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 323 - 334.

12
[ 177429-27-5 ]
[ 188564-67-2 ]

References: [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 323 - 334.

13
[ 177429-27-5 ]
2-[5-Ethoxycarbonyl-3-(ethoxycarbonyl-phosphono-methoxy)-2-hydroxy-phenyl]-2-hydroxy-malonic acid diethyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 323 - 334.

14
[ 177429-27-5 ]
[ 188564-70-7 ]

References: [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 323 - 334.

15
[ 177429-27-5 ]
trisodium [5-carboxy-3-(carboxymethoxy)-2-hydroxyphenyl]hydroxypropanedioate [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 323 - 334.

16
[ 177429-27-5 ]
[ 215876-48-5 ]

Yield	Reaction Conditions	Operation in experiment
65%		EXAMPLE 5 In the same manner as in the above example 2 except for by using <strong>[177429-27-5]2-benzyloxy-5-ethoxycarbonylphenol</strong> instead of 2-benzyloxy-3-fluorophenol, there was obtained (S)-2-hydroxymethyl-6-ethoxycarbonyl-1,4-benzodioxane(1-5) (R4 is EtOCO, and R2, R3 and R5 are H): yield 65%.

References: [1]Patent: US6020503,2000,A .

17
[ 694-28-0 ]
[ 177429-27-5 ]
ethyl 4-benzyloxy-3-(2-oxocyclopentyloxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;	C6: Ethyl 4-benzyloxy-3-(2-oxocyclopentyloxy)benzoate Analogously to Example B6, 34 g of <strong>[177429-27-5]ethyl 4-benzyloxy-3-hydroxybenzoate</strong>, 35 g of potassium carbonate and 15 ml of 2-chlorocyclopentanone give 36 g of the title compound as a colorless oil.

References: [1]Patent: US6121274,2000,A .

18
[ 177429-27-5 ]
[ 183293-47-2 ]

Yield	Reaction Conditions	Operation in experiment
75%		EXAMPLE 7 By using <strong>[177429-27-5]2-benzyloxy-5-ethoxycarbonylphenol</strong> (8.17 g) instead of 2-benzyloxyphenol in the same method described in Example 1, there was obtained 2-tosyloxymethyl-7-ethoxycarbonyl-1,4-benzodioxane (8.85 g, yield 75%).

References: [1]Patent: US5780650,1998,A .

19
[ 5454-83-1 ]
[ 177429-27-5 ]
Ethyl 4-(benzyloxy)-3-(5-methoxy-5-oxopentyloxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%		Step 10a: Ethyl 4-(benzyloxy)-3-(5-methoxy-5-oxopentyloxy)benzoate (Compound 503-18) The title compound 503-18 (1.5 g, 100%) was prepared as a yellow oil from compound 502 (1.0 g, 3.7 mmol), methyl 5-bromopentanoate (1.0 g, 4.4 mmol) using a procedure similar to that described for compound 307-9 (Example 3): LCMS: 437 [M+23]+; 1H NMR (DMSO-d6): delta 7.54 (d, J=8.7 Hz, 1H), 7.44-7.33 (m, 6H), 7.14 (d, J=8.4 Hz, 1H), 5.18 (s, 2H), 4.25 (q, J=7.2 Hz, 2H), 4.01 (t, J=6.0 Hz, 2H), 3.56 (s, 3H), 2.33 (m, 2H), 1.80-1.61 (m, 4H), 1.28 (t, J=7.2 Hz, 3H).

References: [1]Patent: US2009/76044,2009,A1 .Location in patent: Page/Page column 31.

20
[ 3943-89-3 ]
[ 100-44-7 ]
[ 177429-27-5 ]

Yield	Reaction Conditions	Operation in experiment
33%	With potassium carbonate; potassium iodide; In acetonitrile; at 40℃;	Step 9a: Ethyl 4-(benzyloxy)-3-hydroxybenzoate (Compound 502) A mixture of ethyl 3,4-dihydroxybenzoate (9.1 g, 50 mmol), benzyl chloride (6.3 g, 50 mmol), KI (1.66 g, 10 mmol), and K2CO3 (13.8 g, 100 mmol) in acetonitrile (250 mL) was stirred at 40 C. overnight. The mixture was then cooled to room temperature and filtered. The filtrate was evaporated and the residue was purified by column chromatography on silica gel eluding with petroleum ether/ethyl acetate (10/1) to give the title compound 502 as a white solid (4.4 g, 33%): LCMS: 273 [M+1]+; 1H NMR (DMSO-d6): delta 9.49 (s, 1H), 7.35 (m, 7H), 7.08 (d, J=7.8 Hz, 1H), 5.16 (s, 2H), 4.21 (m, 2H), 1.26 (t, J=7.5 Hz, 3H).

References: [1]Patent: US2009/76044,2009,A1 .Location in patent: Page/Page column 30.

21
[ 25542-62-5 ]
[ 177429-27-5 ]
[ 1133461-67-2 ]

Yield	Reaction Conditions	Operation in experiment
100%		Step 9b: Ethyl 4-(benzyloxy)-3-(6-ethoxy-6-oxohexyloxy)benzoate (Compound 503-16) The title compound 503-16 (6.7 g, 100%) was prepared as a yellowish oil from 502 (4.43 g, 16.3 mmol), ethyl 6-bromohexanoate (4.36 g, 19.5 mmol) using a procedure similar to that described for compound 307-9 (Example 3): LCMS: 437 [M+23]+; 1H NMR (DMSO-d6): delta 7.53 (d, J=8.4 Hz, 1H), 7.44-7.31 (m, 6H), 7.14 (d, J=8.4 Hz, 1H), 5.17 (s, 2H), 4.25 (q, J=7.2 Hz, 2H), 4.04-3.98 (m, 4H), 2.26 (t, J=6.9 Hz, 2H), 1.74-1.65 (m, 2H), 1.59-1.52 (m, 2H), 1.46-1.36 (m, 2H), 1.28 (t, J=6.9 Hz, 3H), 1.14 (t, J=7.2 Hz, 3H).
100%		Step 11a: Ethyl 4-(benzyloxy)-3-(6-ethoxy-6-oxohexyloxy)benzoate (compound 503-19) The title compound 503-19 (6.7 g, 100%) was prepared as a yellow oil from compound 502 (4.43 g, 16.3 mmol) and ethyl 6-bromohexanoate (4.36 g, 19.5 mmol) using a procedure similar to that described for compound 503-18 (Example 10): LCMS: 437 [M+23]+; 1H NMR (DMSO-d6): delta 7.53 (d, J=8.4 Hz, 1H), 7.44-7.31 (m, 6H), 7.14 (d, J=8.4 Hz, 1H), 5.17 (s, 2H), 4.25 (q, J=7.2 Hz, 2H), 4.04-3.98 (m, 4H), 2.26 (t, J=6.9 Hz, 2H), 1.74-1.65 (m, 2H), 1.59-1.52 (m, 2H), 1.46-1.36 (m, 2H), 1.28 (t, J=6.9 Hz, 3H), 1.14 (t, J=7.2 Hz, 3H).

References: [1]Patent: US2009/76044,2009,A1 .Location in patent: Page/Page column 30.
[2]Patent: US2009/76044,2009,A1 .Location in patent: Page/Page column 32.

22
[ 29823-18-5 ]
[ 177429-27-5 ]
[ 1133461-96-7 ]

Yield	Reaction Conditions	Operation in experiment
100%		Step 12a: Ethyl 4-(benzyloxy)-3-(7-ethoxy-7-oxoheptyloxy)benzoate (Compound 503-20) The title compound 503-20 (1.6 g, 100%) was prepared as a yellow oil from compound 502 (4.43 g, 16.3 mmol) and ethyl 7-bromoheptanoate (1.0 g, 4.4 mmol) using a procedure similar to that described for compound 503-16 (Example 9): LCMS: 429 [M+1]+.

References: [1]Patent: US2009/76044,2009,A1 .Location in patent: Page/Page column 33.

23
[ 865-50-9 ]
[ 177429-27-5 ]
ethyl 4-(benzyloxy)-3-d3-methoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%		Potassium carbonate (840 mg, 6.08 mmol, 1.52 equiv) was added to a solution of ethyl 4-(benzyloxy)-3-hydroxybenzoate (1.1 g, 4.04 mmol, 1.00 equiv) and N,N-dimethylformamide (10 mL). The mixture was stirred at ambient temperature for about 10 minutes, and then d3-iodomethane (750 mg, 5.17 mmol, 1.10 equiv) was added dropwise. The resulting suspension was stirred at ambient temperature for about 2 hours, and then concentrated in vacuo. Dichloromethane (20 mL) was added to the resulting residue, and the resulting solution was washed water (10 mL). The organic phase was dried, filtered, and concentrated in vacuo to afford the title product as a white solid (1.1 g, yield 94%). LC-MS: m/z=280 (M)+.

References: [1]Patent: US2010/75916,2010,A1 .Location in patent: Page/Page column 17.

24
[ 3943-89-3 ]
[ 177429-27-5 ]

References: [1]Patent: WO2011/53948,2011,A1 .
[2]Tetrahedron,2012,vol. 68,p. 4194 - 4201.

25
[ 82217-54-7 ]
[ 177429-27-5 ]

References: [1]Patent: WO2011/53948,2011,A1 .

26
[ 1195945-43-7 ]
[ 177429-27-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With water; sodium carbonate; In tetrahydrofuran; methanol; at 20℃;Inert atmosphere;	Compound 7 (2.00 g, 6.36 mmol) was dissolved in MeOH/THF (2:1, 45 mL). A solution of sodium carbonate (0.81 g. 7.64 mmol in 15 mL of H2O) was added. The mixture was stirred overnight at room temperature and then concentrated. The residue was partitioned between EtOAc and water. The organic phase was washed with brine and dried (MgSO4). Solvent removal under vacuum gave the product as a white solid (1.66 g, 96%); mp 82-84 C; numax (KBr disc, cm-1) 3383 (OH), 1686 (CO); deltaH (400 MHz, CDCl3) 7.63 (d, 1H, J 1.9 Hz, H-2); 7.61 (dd, 1H, J 1.9, 8.3 Hz, H-6), 7.45-7.35 (5H, m, Bn H), 6.95 (d, 1H, J 8.3 Hz, H-5), 5.70 (br s, 1H, OH), 5.18 (s, 2H, Bn CH2), 4.35 (q, 2H, J 7.1 Hz, CH2CH3), 1.40 (t, 3H, J 7.1 Hz, CH3); deltaC (100.6 MHz, CDCl3) 149.9, 145.4, 135.6, 128.9, 128.7, 127.9, 124.1, 122.6, 115.8, 111.2, 71.1, 60.8, 14.4; m/z (ESI+) 295 [M+Na]+, HRESI+ 295.0945, C16H16NaO4 requires 295.0946.
	With potassium carbonate; In methanol; for 2h;Inert atmosphere; Reflux;	Step 3: 4-Benzyloxy-3-hydroxy-benzoic acid ethyl esterThe compound of step 2 (10 g, 31 .8 mmol) was dissolved in methanol, potassium carbonate (88 mg, 0.636 mmol) was added and the mixture was stirred for 2 h under reflux. The solution was evaporated to dryness and the residue used without further purification.1H-NMR: delta = 9.7 (br s, 1 H); 7.48 (d, 2H); 7.42-7.30 (m, 5H); 7.06 (d, 1 H); 5.19 (s, 2H); 4.22 (q, 2H); 1 .28 (t, 3H)

References: [1]Tetrahedron,2012,vol. 68,p. 4194 - 4201.
[2]Patent: WO2011/53948,2011,A1 .Location in patent: Page/Page column 167.

27
[ 92420-89-8 ]
[ 177429-27-5 ]
[ 1376574-36-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With boron trifluoride diethyl etherate; In dichloromethane; at -20 - 15℃; for 4h;Inert atmosphere; Molecular sieve;	General procedure: Powdered 4 A molecular sieves (5.02 g) were added to a solution of ethyl 4-hydroxybenzoate 4a (0.91 g, 5.00 mmol) and methyl 2,3,4-tri-O-acetyl-1-O-trichloroacetylimidoyl-alpha-d-glucopyranuronate 8 (3.35 g, 7.00 mmol) in dry DCM (20 mL). The mixture was cooled to -20 C and BF3·Et2O (0.246 mL, 2.00 mmol) was added dropwise. The mixture was allowed to warm gradually to 15 C under continued stirring for 4 h. The reaction was quenched with triethylamine and the mixture was then filtered through a pad of Celite and concentrated. The residue was purified by column chromatography (Silica gel, Pet ether/EtOAc 3:1 to 2.5: 2) giving rise to the glucuronide conjugate as an off-white solid (2.20 g, 92%).

References: [1]Tetrahedron,2012,vol. 68,p. 4194 - 4201.

28
[ 100-44-7 ]
[ 177429-27-5 ]

References: [1]Tetrahedron,2012,vol. 68,p. 4194 - 4201.

29
[ 78728-00-4 ]
[ 177429-27-5 ]

References: [1]Tetrahedron,2012,vol. 68,p. 4194 - 4201.

30
[ 177429-27-5 ]
[ 953037-17-7 ]

References: [1]Tetrahedron,2012,vol. 68,p. 4194 - 4201.

31
[ 177429-27-5 ]
5-carboxy-2-hydroxyphenyl-β-D-glucopyranosiduronic acid dipotassium salt [ No CAS ]

References: [1]Tetrahedron,2012,vol. 68,p. 4194 - 4201.

32
[ 78-77-3 ]
[ 177429-27-5 ]
[ 1574286-14-8 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol;Reflux;	Compound (3) (5.3 g), ethanol (75 ml), and DBU (8.9 g) were introduced into a reaction vessel, and isobutyl bromide (4b) (8 ml, 3 eq. ) was added thereto. The mixture was heated at reflux overnight. After the mixture was cooled to room temperature, the mixture was concentrated by distilling off ethanol in vacuo. AcOEt (50 ml) was added thereto, and extraction and liquid separation was performed. After the organic layer was washed with water (50 ml) twice, it was concentrated to dryness to give a solid of ethyl 4-(benzyloxy)-3-isobutoxybenzoate. Acetonitrile (50 ml) was added to the resulting solid, followed by dissolution, and a 10% NaOH aqueous solution (28 ml) was added thereto. The resulting mixture was heated under stirring at 40C or more overnight. After the completion of the reaction, concentrated hydrochloric acid was added. After the reaction mixture was cooled, the precipitated crystals were collected by filtration, and dried at 80C to give white crystal Compound (5b) (4.67 g) . Compound (5b): 1H NMR (CDCl3, 300 MHz) delta 1.07 (d, J = 6.9 Hz, 6H) , 2.18 (sept, J = 6.9 Hz, 1H), 3.85 (d, J = 6.9 Hz, 2H) , 5.22 (s, 2H) , 6.94 (d, J = 8.4 Hz, 1H), 7.29- 7.4 7 (m, 5H) , 7.60 (d, J = 1.8 Hz, 1H) , 7.69 (dd, J = 8.4 Hz, 1.8 Hz, 1H).

References: [1]Patent: WO2014/34958,2014,A1 .Location in patent: Page/Page column 54-55.

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References: [1]Patent: WO2014/34958,2014,A1 .

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References: [1]Patent: WO2014/34958,2014,A1 .

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References: [1]Patent: WO2014/34958,2014,A1 .

Historical Records

Technical Information

• Acidity of Phenols • Acyl Group Substitution • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Electrophilic Substitution of the Phenol Aromatic Ring • Ester Cleavage • Etherification Reaction of Phenolic Hydroxyl Group • Halogenation of Phenols • Nomenclature of Ethers • Oxidation of Phenols • Pechmann Coumarin Synthesis • Preparation of Aldehydes and Ketones • Preparation of Ethers • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers • Reactions with Organometallic Reagents • Reimer-Tiemann Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents

Related Functional Groups of
[ 177429-27-5 ]

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CAS No.: 177429-27-5

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