103260-44-2|Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate| Ambeed

Structure of 103260-44-2

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Quality Control of [ 103260-44-2 ] Purity: 98% SDS Specification

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Product Details of [ 103260-44-2 ]

CAS No. :	103260-44-2
Formula :	C₉H₁₆O₃
M.W :	172.22
SMILES Code :	O=C(OCC)CC1CCOCC1
MDL No. :	MFCD03788560
InChI Key :	JLMMMEDWRUVCEW-UHFFFAOYSA-N
Pubchem ID :	2773412

Safety of [ 103260-44-2 ]

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

Application In Synthesis of [ 103260-44-2 ]

* 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 [ 103260-44-2 ]

[ 103260-44-2 ] Synthesis Path-Downstream 1~35

1
[ 103260-44-2 ]
[ 4677-18-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydroxide; In tetrahydrofuran;	2-(4-Oxanyl)ethanol To a stirring suspension of lithium aluminum hydride (5.10 g, 138 mmol) in THF (200 mL) at 0 C. was added drop-wise a solution of ethyl 2-(4-oxanyl)acetate (22.0 g, 138 mmol) in THF (50 mL). The reaction mixture was then heated at reflux overnight. After cooling the mixture in an ice bath, ether (300 mL) was added, followed by drop-wise addition of 5N NaOH, until the formation of heavy white precipitate is complete. The suspension was filtered and the filtrate dried (K2CO3), filtered and concentrated by rotary evaporation to give a colorless liquid (17.7 g, 100%).
93%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 0.5h;Inert atmosphere;	c) To a solution of 425 mg (2.5 mmol) of ethyl 2-(tetrahydro-2H-pyran-4- yl)acetate in 10 mL of dry THF cooled at 05C under argon, a 2.71 mL of a solution of LiAII-U 1 M in THF was added. Bubbling was observed. It was stirred at room temperature for 30 min. Then it was quenched with wet EtAcO, dried with MgS04 and filtered through celite, washing with abundant EtAcO. After removing the solvent the desired compound, 2-(tetrahydro-2H-pyran-4-yl)ethanol, was obtained (300 mg, 93%).
77%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 11 - 13℃; for 18h;	To a mixture of <strong>[103260-44-2]ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate</strong>(20 g, 116 mmol) in anhydrous THF (300 mE) was addedlithium aluminum hydride (8.8 g, 232 mmol) portionwise at0 C. The mixture was stirred at 11-13 C. for 18 h. TEC(petroleum ether: ethyl acetate=3: 1) showed no startingmaterial remaining. The mixture was quenched with water(9 mE), 10% aq. NaOH solution (9 mE) and water (18 mE)successively at 0 C., filtered and concentrated underreduced pressure to give crude 2-(tetrahydro-2H-pyran-4-yl)ethanol (11.7 g, 77%) as an oil, which was used for thenext step directly without further purification. ?H NMR(CDC13, 400 MHz): oe 3.86-3.90 (m, 2H), 3.58-3.61 (t, J=6.4Hz, 2H), 3.32-3.35 (t, J=11.6 Hz, 2H), 2.69-2.70 (m, 1H),1.61-1.63 (m, 3H), 1.54-1.60 (m, 2H), 1.43-1.45 (m, 2H).

66.1%	With lithium aluminium tetrahydride; In tetrahydrofuran; ethyl acetate; at 0℃; for 16h;	Lithium aluminum hydride (2M solution in THF, 40.66 ml, 81.3 mmol) was cooled at 0 C and a solution of <strong>[103260-44-2]ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate</strong> (14.0 g, 81.3 mmol) in THF (70 ml) was added dropwise. Ethyl acetate (20 ml) was added to the reaction mixture dropwise at 0 C and the resulting mixture was allowed to stir for 16 h. The reaction mixture was filtered through Celite and the filtrate was concentrated to give crude compound. The crude material was purified by column chromatography using mobile phase 0-65% ethyl acetate in hexane to afford the title compound (66.1%). ?H NMR (400MHz, CDC13) & 5.71 (s, 1H), 4.18-4.15 (m, 2H), 3.81-3.75 (m, 4H), 3.05-3.02 (m, 2H), 2.37-2.34 (m, 2H), 1.32- 1.31 (m, 3H).
		To 15 mL of tetrahydrofuran (THF) at 0 0C was added LiAlH4 (0.28 g, 7.3 mmol). This mixture was stirred for 10 min then the ethyl tetrahydropyran-4-yl-acetate (Combi- Blocks Inc., 0.50 g, 2.9 mmol) was added. The reaction was stirred for 5 min at 0 0C then was allowed to warm to ambient temperature and was stirred for 90 min. The reaction was quenched with excess NaHSO4-IOH2O and was stirred for 60 min. The mixture was filtered through Celite. The filtrate was concentrated to give the title compound which was carried on without further purification. MS (DCI/NH3) m/z 131 (M+H)+. EPO <DP n="41"/>
		To a suspension of lithium aluminium hydride (11 g, 0.29 mol) in dry tetrahydrofuran (350 mL) at 0 C. was added a solution of (tetrahydro-pyran-4-yl)-acetic acid ethyl ester (25 g, 0.145 mol) in dry tetrahydrofuran (100 mL) dropwise. The resulting mixture was then refluxed for 16 h. After cooling to 0 C., the reaction mixture was quenched carefully by slow addition of a saturated sodium carbonate solution (50 mL). The mixture was decanted and the precipitate was washed with tetrahydrofuran (2×200 mL). The combined tetrahydrofuran layers were dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-(tetrahydro-pyran-4-yl)-ethanol (13 g, 69%) as a yellow oil which was used in the next step without purification.
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 13℃; for 18h;	[00106] To a mixture of <strong>[103260-44-2]ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate</strong> (20 g, 116 mmol) in anhydrous THF (300 mL) was added lithium aluminum hydride (8.8 g, 232 mmol) portionwise at 0 C. The mixture was stirred at 11-13 C for 18 h. TLC (petroleum ether: ethyl acetate = 3: 1) showed no starting material remaining. The mixture was quenched with water (9 mL), 10% aq. NaOH solution (9 mL) and water (18 mL) successively at 0 C, filtered and concentrated under reduced pressure to give crude 2-(tetrahydro-2H-pyran-4- yl)ethanol (11.7 g, 77%) as an oil, which was used for the next step directly without further purification. 1H NMR (CDC13, 400 MHz): delta 3.86-3.90 (m, 2H), 3.58-3.61 (t, J = 6.4 Hz, 2H), 3.32-3.35 (t, J = 11.6 Hz, 2H), 2.69-2.70 (m, 1H), 1.61-1.63 (m, 3H), 1.54-1.60 (m, 2H), 1.43-1.45 (m, 2H).
		Intermediate 32: 2-(Tetrahydro-2/-/-pyran-4-yl)ethanolTo an ice-cold solution of lithium aluminium hydride (12.6 ml, 2.3M solution in tetrahydrofuran) in dry tetrahydrofuran (20 ml) and under nitrogen, was added a solution of ethyl tetrahydro-2/-/-pyran-4-yl acetate (5g) in dry tetrahydrofuran dropwise over 10 minutes. Following the addition the reaction was heated to reflux, overnight. The reaction was cooled and diluted with diethyl ether (100 ml). A 5M aqueous solution of sodium hydroxide (-10 ml) was added cautiously to the reaction mixture until the effervescence ceased. The formed white precipitate was filtered off. The resulting filtrate was dried over potassium carbonate, filtered and concentrated in vacuo. This yielded the title compound as a colourless oil (3.3g). MS calcd for (C7H14O2)" = 130 MS found (electrospray): (M+H)+ = 1311 H NMR (DMSO): 4.35 (1 H, t), 3.80 (2H, m), 3.43 (2H, m), 3.25 (2H, m), 1.60 (1 H, m), 1.54 (2H, m), 1.35 (2H, m), 1.13 (2H, m).

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 9909 - 9911.
[2]Patent: US2004/220214,2004,A1 .
[3]Patent: WO2013/37960,2013,A1 .Location in patent: Page/Page column 76.
[4]Patent: US9481674,2016,B1 .Location in patent: Page/Page column 31; 32.
[5]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 6309 - 6323.
[6]Patent: WO2016/44626,2016,A1 .Location in patent: Paragraph 00485.
[7]Justus Liebigs Annalen der Chemie,1937,vol. 532,p. 80.
Chem.Abstr.,1940,p. 4396.
[8]Patent: WO2006/69196,2006,A1 .Location in patent: Page/Page column 39.
[9]Patent: US2011/144105,2011,A1 .Location in patent: Page/Page column 54-55.
[10]Patent: WO2016/61160,2016,A1 .Location in patent: Paragraph 00106.
[11]Patent: WO2008/101867,2008,A1 .Location in patent: Page/Page column 70.

2
[ 130312-00-4 ]
[ 103260-44-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	Pd/NH4COOH; at 80℃;	Ethyltetrahydro-4H-pyran-4-ylacetate was prepared from ethyltetrahydro-4H-pyran-4-ylideneacetate (16.0 g, 94 mmol) and Pd/ NH4COOH at 80 C. Colorless oil, Yield: 16.3 g, quantitaive), MS: 173.2 (M+H)+
99%	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; under 760.051 Torr;	b) To a solution of 425 mg (2.5 mmol) of ethyl 2-(dihydro-2H-pyran-4(3H)- ylidene)acetate in 15 mL of MeOH, 133 mg of Pd on carbon 10% was added. Hydrogen atmosphere was set (1 atm, with a balloon) and the reaction was stirred at room temperature overnight. It was filtered through a pad of celite washing with abundant EtAcO. After removing the solvent the desired compound ethyl 2- (tetrahydro-2H-pyran-4-yl)acetate was obtained as a colorless oil (99%).
98.5%	palladium-carbon; In ethanol;	Ethyl 2-(4-oxanyl)acetate To a solution of ethyl 2-(4-oxanylidene)acetate (22.0 g, 139 mmol) in ethanol (50 mL) was added 10% Pd/C (2.2 g) and the mixture subjected to hydrogenation overnight on a Parr apparatus (50 psi). The catalyst was removed by filtration through Celite, which was washed with ethanol (25 mL). Removal of solvent from the combined filtrates by rotary evaporation gave the desired product as a colorless oil (22.0 g, 98.5%).

94%	With palladium on activated charcoal; hydrogen; In methanol; at 16 - 19℃; under 1551.49 Torr; for 18h;	A mixture of ethyl 2-(dihydro-2H-pyran-4(3H)-ylidene) acetate (21 g, 123 mmol) and dry Pd/C (2.5 g) in methanol (300 mE) was stirred at 16-19 C. for 18 h under H2 (30 psi). TEC (petroleum ether:ethyl acetate=3:1) showed no starting material remaining. The mixture was filtered and the filtrate was concentrated under reduced pressure to give crude ethyl5 2-(tetrahydro-2H-pyran-4-yl)acetate (20 g, 94%) as an oil, which was used for the next step directly without further purification. ?H NMR (CDC13, 400 MHz): oe 4.11-4.15 (q, J=7.2 Hz, 2H), 3.93-3.95 (d, J=10.8 Hz, 2H), 3.37-3.43 (t, J=11.6 Hz, 2H), 2.23-2.25 (d, J=6.8 Hz, 2H), 1.99-2.03 (m,10 1H), 1.62-1.65 (m, 2H), 1.32-1.36 (m, 2H), 1.24-1.27 (t, J=7.2 Hz, 3H).
84%	With sodium tetrahydroborate; nickel dichloride; In methanol; at 0℃; for 0.5h;	To a solution of ethyl 2-(tetrahydro-4H-pyran-4-ylidene)acetate (0.4 g, 2.33 mmol) in methanol (5 ml) was added NaBH4 (0.198 g, 5.29 mmol) portionwise at 0 C. After 30 mm of stirring at 0 C NiC12 (0.12 g, 0.505 mmol) was added slowly. After stirring for 45mm the reaction solvent was evaporated under reduced pressure and diluted with water (10 ml) and the product was extracted with ethyl acetate (3x 10 ml). The combined organic layer was concentrated under reduced pressure to afford the title compound (84%). ?H NMR (400MHz, CDC13) & 4.18-4.13 (q, 1=7.2Hz, 2H), 3.99-3.95 (m, 2H), 3.46-3.40 (m, 2H), 2.27-2.25 (m, 2H), 2.10-1.98 (m, 1H), 1.64 (s, 2H), 1.41-1.23 (m, 5H).
78%	With palladium 10% on activated carbon; ammonium formate; In methanol; at 70℃; for 15h;	To a mixture composed of ethyl 2-(2H-pyran-4(3H,5H,6H)-ylidene)acetate (10 g, 58.75 mmol) and ammonium formate (37 g, 587.54 mmol) in methanol (150 ml) was added 10% Pd-carbon (1.0 g) at room temperature, and the mixture was stirred at 70 C for 15 hr. The reaction mixture was allowed to cool to room temperature, and the catalyst was collected by filtration through Celite pad and was washed with methanol. The filtrate was concentrated under reduced pressure, and the residue was chromatographed on silica gel column (hexane:ethyl acetate = 94:6) to give the title compound as an oil (7.9 g, yield 78%). 1H-NMR (400 MHz, CDCl3): delta (ppm) 4.13 (q, J = 7.2 Hz, 2H ), 3.97-3.93 (m, 2H), 3.44-3.38 (m, 2H), 2.24 (d, J = 7.2 H z, 2H), 2.08-1.92 (m, 1H) 1.66-1.62 (m, 2H), 1.40-1.29 (m, 2H), 1.26 (t, J = 7.2 Hz, 3H); MS (ESI): m/z 172 (M+).
	With hydrogen;palladium 10% on activated carbon; In methanol; at 25℃; under 1551.49 Torr; for 20h;	A mixture of (tetrahydro-pyran-4-ylidene)-acetic acid ethyl ester (27 g, 159 mmol) and 10% palladium on activated carbon (3 g) in methanol (300 mL) was stirred at 25 C. under 30 psi of hydrogen for 20 h. The catalyst was filtered off, washed with ethyl acetate and concentrated in vacuo to afford (tetrahydro-pyran-4-yl)-acetic acid ethyl ester (25 g, 91%) as a colorless oil which was used in the next step without purification.
	With palladium on activated charcoal; hydrogen; In methanol; at 16 - 19℃; under 1551.49 Torr; for 18h;	[00105] A mixture of ethyl 2-(dihydro-2H-pyran-4(3H)-ylidene)acetate (21 g, 123 mmol) and dry Pd/C (2.5 g) in methanol (300 mL) was stirred at 16-19 C for 18 h under H2 (30 psi). TLC (petroleum ether: ethyl acetate = 3: 1) showed no starting material remaining. The mixture was filtered and the filtrate was concentrated under reduced pressure to give crude ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (20 g, 94%) as an oil, which was used for the next step directly without further purification. 1H NMR (CDC13, 400 MHz): delta 4.11-4.15 (q, J = 7.2 Hz, 2H), 3.93-3.95 (d, J = 10.8 Hz, 2H), 3.37-3.43 (t, J = 11.6 Hz, 2H), 2.23-2.25 (d, J = 6.8 Hz, 2H), 1.99-2.03 (m, 1H), 1.62-1.65 (m, 2H), 1.32-1.36 (m, 2H), 1.24-1.27 (t, J = 7.2 Hz, 3H).

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6255 - 6269.
[2]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 6309 - 6323.
[3]Patent: US6340691,2002,B1 .Location in patent: Page column 66.
[4]Patent: EP1147080,2004,B1 .Location in patent: Page 49.
[5]Patent: WO2013/37960,2013,A1 .Location in patent: Page/Page column 76.
[6]Journal of Organic Chemistry,2006,vol. 71,p. 9909 - 9911.
[7]Patent: US2004/220214,2004,A1 .
[8]Bioscience, Biotechnology and Biochemistry,1994,vol. 58,p. 647 - 651.
[9]Patent: US9481674,2016,B1 .Location in patent: Page/Page column 31; 32.
[10]Patent: WO2016/44626,2016,A1 .Location in patent: Paragraph 00484.
[11]Patent: EP2737900,2014,A1 .Location in patent: Paragraph 0114; 0116-0117.
[12]Justus Liebigs Annalen der Chemie,1937,vol. 532,p. 80.
Chem.Abstr.,1940,p. 4396.
[13]Journal of Medicinal Chemistry,1993,vol. 36,p. 2300 - 2310.
[14]Patent: US2011/144105,2011,A1 .Location in patent: Page/Page column 54.
[15]Patent: WO2016/61160,2016,A1 .Location in patent: Paragraph 00105.

3
[ 67-56-1 ]
[ 103260-44-2 ]
[ 156002-64-1 ]

References: [1]Bioscience, Biotechnology and Biochemistry,1994,vol. 58,p. 647 - 651.

4
[ 71-23-8 ]
[ 103260-44-2 ]
n-propyl tetrahydropyran-4-acetate [ No CAS ]

References: [1]Bioscience, Biotechnology and Biochemistry,1994,vol. 58,p. 647 - 651.

5
[ 103260-44-2 ]
[ 85064-61-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With water; sodium hydroxide; In methanol; at 0 - 20℃; for 15h;	A solution of sodium hydroxide (15.9 g, 44.06 mmol) in water (150 ml) was added dropwise to a solution of <strong>[103260-44-2]ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate</strong> (15 g, 8.81 mmol) in methanol (150 ml) at a temperature of 0 C or below, and the mixture was stirred at room temperature for 15 hr. The solvent of the reaction mixture was removed by distillation under reduced pressure, and the water layer was adjusted to pH 3 by the addition of 1 M hydrochloric acid and was extracted with ethyl acetate. The organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate, and the filtrate was concentrated under reduced pressure to give a corresponding acid as a colorless solid (12.0 g, 94%). This compound was used in the next step without further purification. Benzyl bromide (14.3 g, 83.33 mmol) was added dropwise to a suspension of this compound (10.0 g, 69.44 mmol) and anhydrous potassium carbonate (28.8 g, 208.3 mmol) in acetonitrile (100 ml) at room temperature, and the mixture was refluxed for 48 hr. The solvent of the mixture was removed by distillation under reduced pressure, the residue was diluted with water and was extracted with dichloromethane, and the organic layer was dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure, and the residue was chromatographed on silica gel column (hexane:ethyl acetate = 9:1) to give the tile compound as an oil (12.0 g, yield 75%). 1H-NMR (400 MHz, CDCl3): delta (ppm) 7.39-7.34 (m, 5H), 5.12 (s, 2H), 3.95-3.92 (m, 2H), 3.42-3.36 (m, 2H), 2.30 (d, J = 7.2 Hz, 2H), 2.09-1.99 (m, 1H) 1.64-1.61 (m, 2H), 1.39-1.29 (m, 2H); MS (ESI): m/z 234 (M+).
	With sodium hydroxide; In methanol; water;	Preparatory Example 33 4-Tetrahydropyranylacetic acid STR234 20 ml of methanol, 10 ml of water and 1 g of sodium hydroxide were added to 0.9 g of ethyl 4-tetrahydropyranylacetate and agitated at 80 C. for 1 hour. The solvent was removed by distillation, to which water was added. After washing with ethyl acetate, a hydrochloric acid aqueous solution was added to the resultant aqueous phase to an extent of pH of 3, followed by extraction with chloroform under salting-out conditions and drying with anhydrous magnesium sulfate. This was removed by filtration and the solvent was distilled off, thereby obtaining 0.87 g of a crude intended compound. 1 H-NMR(CDCl3) delta:1.0-2.4(m,5H), 2.28(bd,J=6.5 Hz,2H), 3.37(td,J=11.5 Hz,2.9 Hz,2H), 3.7-4.1(m,2H), 7.85(bs,1H)
	With potassium hydroxide; In ethanol; for 18h;	The product of Preparative Example 11 (3.04) g, 17.7 mmol) was dissoloved in 90 mL of ethanol containing 3 g (53 mmol) of potassium hydroxide. This was stirred for 18 hours and then concentrated under vacuum. The residue was dissolved in 15 mL of water, adjusted to pH 2 with 12 N HCl, and extracted with three 50 mL portions of dichloromethane. The combined organic layers were dried over magnesium sulfate and concentrated under vacuum giving 2.04 g of the product as a white solid, mp = 60-63C.

References: [1]Patent: EP2737900,2014,A1 .Location in patent: Paragraph 0114; 0117-0118.
[2]Journal of Medicinal Chemistry,1993,vol. 36,p. 2300 - 2310.
[3]Patent: US5221671,1993,A .
[4]Patent: EP1019398,2004,B1 .Location in patent: Page 51.

Yield	Reaction Conditions	Operation in experiment
		Preparatory Example 32 Ethyl 4-tetrahydropyranylacetate STR233 2.0 g of ethyl tetrahydropyran-Delta4,a -acetate was dissolved in 50 ml of methanol, to which 10% palladium-carbon was added, followed by hydrogenation for 3 hours. After removal of the catalyst by filtration, the reaction mixture was concentrated under reduced pressure to obtain 1.6 g of the intended compound. 1 H-NMR(CDCl3) delta:1.1-2.3(m,7H), 1.3(t,J=7,2 Hz,3H), 3.2-3.6(td,J=12,6 Hz,2.9 Hz,2H), 3.8-4.3(m,2H), 4.1(q,J=7.2 Hz,2H)
		PREPARATIVE EXAMPLE 11 Ethyl tetrahydropyran-4-acetate A mixture of 15.0 and 16.0 (3 g, 17.6 mmol) from Preparative Example 10 was dissolved in 20 mL of ethyl acetate containing 1.0 g of 10% paladium on carbon. This mixture was stirred for 18 hours under an atmosphere of hydrogen. The catalyst was filtered and the filtrate was concentrated under vacuum giving 3.04 g of the title product as a colorless oil.
		PREPARATIVE EXAMPLE 27 Ethyl tetrahydropyran-4-acetate Following a procedure described in Liebigs Ann. Chem. (1982) 250, if one were to react ethyl tetrahydro-4-ylidenyl-carboxylate, product 15.0 of Preparative Example 10, with an excess of sodium cyanide at 80-100 C. one would obtain the product.

EXAMPLE 219B ethyl tetrahydro-2H-pyran-4-ylacetate A mixture of Example 219A (1 g) and 10% Pd/carbon (100 mg) in methanol(30 mL) was stiffed under hydrogen for 3.5 h, then filtered through a pad of celite and concentrated to give 0.97 g of the title compound.

7
[ 103260-44-2 ]
[ 287202-47-5 ]
[ 287393-54-8 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6255 - 6269.
[2]Patent: US6340691,2002,B1 .Location in patent: Page column 66.

8
[ 29943-42-8 ]
[ 103260-44-2 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 9909 - 9911.
[2]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 6309 - 6323.
[3]Journal of Medicinal Chemistry,2004,vol. 47,p. 6255 - 6269.
[4]Bioscience, Biotechnology and Biochemistry,1994,vol. 58,p. 647 - 651.
[5]Journal of Medicinal Chemistry,1993,vol. 36,p. 2300 - 2310.
[6]Patent: US2011/144105,2011,A1 .
[7]Patent: EP2737900,2014,A1 .
[8]Patent: WO2016/61160,2016,A1 .
[9]Patent: WO2016/44626,2016,A1 .
[10]Patent: US9481674,2016,B1 .
[11]Patent: WO2013/37960,2013,A1 .

9
[ 103260-44-2 ]
[ 4677-20-7 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 9909 - 9911.
[2]Patent: WO2016/44626,2016,A1 .
[3]Patent: US2004/220214,2004,A1 .
[4]Patent: WO2013/37960,2013,A1 .
[5]Patent: WO2008/101867,2008,A1 .

10
[ 103260-44-2 ]
[ 428871-01-6 ]

11
[ 103260-44-2 ]
[ 921755-42-2 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 9909 - 9911.

12
[ 103260-44-2 ]
[ 65626-23-5 ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 6309 - 6323.
[2]Patent: US2011/144105,2011,A1 .
[3]Patent: WO2016/61160,2016,A1 .
[4]Patent: US9481674,2016,B1 .

13
[ 103260-44-2 ]
(4-but-2-ynyloxy-benzenesulfonyl)-(tetrahydro-pyran-4-yl)-acetyl chloride [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6255 - 6269.

14
[ 103260-44-2 ]
[ 287393-55-9 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6255 - 6269.

15
[ 103260-44-2 ]
2-[4-(2-Butynyloxy)phenyl]sulfonyl}-N-hydroxy-2-tetrahydro-2H-pyran-4-yl-acetamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6255 - 6269.

16
[ 103260-44-2 ]
C₁₂H₂₀O₄ [ No CAS ]