178306-47-3|Methyl 2-hydroxy-3-methoxy-3,3-diphenylpropanoate| Ambeed

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Quality Control of [ 178306-47-3 ] Purity: 97% SDS Specification

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Product Details of [ 178306-47-3 ]

CAS No. :	178306-47-3
Formula :	C₁₇H₁₈O₄
M.W :	286.32
SMILES Code :	O=C(OC)C(O)C(C1=CC=CC=C1)(OC)C2=CC=CC=C2
MDL No. :	MFCD09833706
InChI Key :	BEPLSLADXOJCBY-UHFFFAOYSA-N
Pubchem ID :	10541193

Safety of [ 178306-47-3 ]

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

Application In Synthesis of [ 178306-47-3 ]

* 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 [ 178306-47-3 ]

[ 178306-47-3 ] Synthesis Path-Downstream 1~35

1
[ 57268-32-3 ]
[ 178306-47-3 ]
[ 1025849-08-4 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2123 - 2128.

2
[ 67-56-1 ]
[ 76527-25-8 ]
[ 178306-47-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With boron trifluoride diethyl etherate; at 0 - 20℃; for 14h;	5 g (19.6 mmol) of methyl 3,3-diphenyl-2,3-epoxypropionate,Was dissolved in 50 ml of anhydrous methanol,0.1 ml of boron trifluoride etherate was added at 0 C.The mixture was stirred at 0 C. for 2 hours,The mixture was further stirred at room temperature for 12 hours.The solvent was distilled off, The residue was placed in ethyl acetate,Washed with sodium bicarbonate and water,And dried over magnesium sulfate.After removing the solvent by distillation,5.5 g (88%) of a pale yellow oil remained.
84%	With toluene-4-sulfonic acid; at 0℃; for 2h;	500 g (2.74 mol) of benzophenone was dissolved in 1200 mL of toluene. After purging with nitrogen, 267 g (4.94 mol) of sodium methoxide was added and the suspension was stirred. The suspension was cooled and a solution of 410 mL (4.68 mol) of methyl chloroacetate in toluene (300 mL) was slowly added dropwise over 90 minutes while maintaining the temperature at -8 to 4 C., and then the solution was cooled to -3 to 4 C. For 1 hour. After adding 1000 mL of water and stirring for 15 minutes, the organic layer obtained by liquid-liquid separation was washed with 1000 mL of water. The solvent was distilled off under reduced pressure, and the obtained residue (methyl (RS) -3,3-diphenyl-2,3-epoxypropenoate) was dissolved in 1200 mL of methanol and cooled at 0 C. to obtain p- A solution of 15 g (0.08 mol) of toluenesulfonic acid monohydrate in methanol (150 mL) was slowly added dropwise over 30 minutes. The mixture was stirred at 0 C. for 1.5 hours, and the precipitated crystals were collected by filtration. The obtained crystals were dissolved in 2500 mL of ethyl acetate and washed twice with 1000 mL of 5% sodium carbonate aqueous solution. The solvent was distilled off under reduced pressure, 1000 mL of hexane was added to the obtained residue, suspended and stirred at room temperature for 1.5 hours, and then stirred at 0 C. for 1 hour. The crystals were collected by filtration and dried under reduced pressure at 60 C. for 5 hours to obtain 659 g (yield: 84%) of methyl (RS) -2-hydroxy-3-methoxy-3,3-diphenylpropanoate.
75%		Step-II : preparation of methyl- 2-hydroxy-3-methoxy-3,3-diphenyl propionate (III) :Into a 5L round bottomed flask a mixture of methanol(1.2L) and compound of formula - I (660g) from the previous step were charged and stirred for 15 minutes. p-Toluene sulphonic acid(15g dissolved in 150ml methanol) was slowly added during 30 minutes at 25-55C. The reaction mass was brought to room temperature, maintained at the same temperature for 2hours was filtered and the filtered compound was dissolved in ethyl acetate(3L). Ethyl acetate layer was washed with 5% sodium bicarbonate solution(2xlL). Ethyl acetate layer was distilled off completely under vacuum. To the residue hexane(l L) was charged and maintained under stirring for 2hours. The product was filtered and dried at 50-60C Dry weight : 560g (75%)Purity by HPLC : 99.9%Melting range : 100-102C

	toluene-4-sulfonic acid; at 0 - 35℃;	Example-1: Preparation of 2-hydroxy-3-methoxy-3,3-diphenylpropionic acid methyl ester compound of formula-5a:Mixture of benzophenone (100 grams) and methyl chloroacetate (84 grams) in tetrahydrofuran (160 ml) was added to a cooled mixture of tertrahydrofuran and sodium methoxide (51.8 grams) at below -4C in 90 minutes, stirred for 30 minutes at -10C to -5C. The reaction mixture temperature was raised to 25-35C, quenched with water and then extracted with ethyl acetate. The organic layer was washed with brine solution and dried over sodium sulphate. The organic layer was distilled under reduced pressure at 60C and methanol was added to the obtained residue then methanol was distilled off completely. The reaction mixture cooled to 25-35C and methanol (280 ml) was added to it. Paratoluene sulfonic acid (4 grams) was added to the above reaction mixture. The reaction mixture was stirred for 2 hours at 25-35C and then cooled to 0-50C and stirred 45 minutes. The obtained solid was filtered, washed with methanol and then dried at 50-60C to get the title compound. Yield: 110 grams; M.R: 92-96C
	With boron trifluoride diethyl etherate; at 0℃; for 2h;	140 g of methyl 3,3-diphenyloxirane-2-carboxylate was dissolved in 280 ml of methanol and then cooled to 0C .6.9 ml of BF3OEt2 was added slowly and stirred at 0C for 2 hours. When the methyl 3,3-diphenyloxirane-2-carboxylate disappears completely and methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate is produced,65.8 g of NaOH was dissolved in 980 ml of water and slowly added dropwise. Methanol (140 ml) was added, the temperature was raised to 45 to 50C, and the mixture was stirred for 1 hour. When the reaction was completed, the methanol was distilled off under reduced pressure, and diluted with 700 ml of dichloromethane. 300 ml of 6N HCl aqueous solution was added to adjust the pH to 2, and the organic layer was separated. The organic layer was washed with 300 ml of brine, dried, filtered and distilled under reduced pressure, and recrystallized from 500 ml of hexane to obtain 123 g of 2-hydroxy-3-methoxy-3,3-diphenylpropionic acid (yield: 82%).
5.33 kg	With boron trifluoride diethyl etherate;Large scale;	The oily product of Example 1 was methyl 3,3-diphenyl-2,3-epoxypropionate (5.54 kg) and methanol (15).L) was charged into the reaction vessel, and boron trifluoride etherate (BF3-ether) (148 ml) was added dropwise.After the reaction is completed, water (15 L) is added to the reaction system to quench the reaction.The reaction mixture was extracted three times with diethyl ether (7 L) and then evaporated.Filter and collect solids,Drying yielded 5.33 kg of methyl 2-hydroxy-3-methoxy-3,3-diphenylpropanoate in a two step yield of 85%.

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2123 - 2128.
[2]Patent: JP5700378,2015,B2 .Location in patent: Paragraph 0062.
[3]Patent: JP2017/128528,2017,A .Location in patent: Paragraph 0005; 0039.
[4]Patent: WO2012/17441,2012,A1 .Location in patent: Page/Page column 10-11.
[5]Patent: WO2010/70658,2010,A2 .Location in patent: Page/Page column 18.
[6]New Journal of Chemistry,2014,vol. 38,p. 3050 - 3061.
[7]Patent: KR2016/39907,2016,A .Location in patent: Paragraph 0095.
[8]Organic Process Research and Development,2018,vol. 22,p. 1200 - 1207.
[9]Patent: CN104592129,2019,B .Location in patent: Paragraph 0037; 0038; 0039; 0040; 0041; 0042; 0043.

3
[ 77166-01-9 ]
[ 178306-47-3 ]
[ 1025933-19-0 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2123 - 2128.

4
[ 113583-35-0 ]
[ 178306-47-3 ]
[ 178306-45-1 ]

Yield	Reaction Conditions	Operation in experiment
82%		2.8 6 g (10 mmol) of <strong>[178306-47-3]methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate</strong> were dissolved in 40 ml of dimethylformamide,Then 0.3 g (12 mmol) sodium hydride was added.The mixture was stirred for 1 hour,Then 2.2 g (10 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine was added.After stirring at room temperature for 24 hours,Carefully hydrolyze with 10 ml of water,The pH was adjusted to 5 with acetic acid,The solvent was removed by distillation under high vacuum.The residue was placed in 100 ml of ethyl acetate,Wash with water,And dried over magnesium sulfate,The solvent was distilled off.The residue was mixed with 10 ml of ether,The resulting precipitate was collected by suction filtration.After drying, 3.48 g (82%) of a white powder remained. Melting point 81 C.
	In N-methyl-acetamide; water; ethyl acetate;	Example 3 Methyl 2-(4,6-dimethoxy-pyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate 2.86 g (10 mmol) of <strong>[178306-47-3]methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate</strong> were dissolved in 40 ml of dimethylformamide, and 0.3 g (12 mmol) of sodium hydride was added. The mixture was stirred for 1 h and then 2.2 g (10 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine were added. After stirring at room temperature for 24 h, cautious hydrolysis was carried out with 10 ml of water, the pH was adjusted to 5 with acetic acid, and the solvent was removed by distillation under high vacuum. The residue was taken up in 100 ml of ethyl acetate, washed with water and dried over magnesium sulfate, and the solvent was distilled out. The residue was mixed with 10 ml of ether, and the resulting precipitate was filtered off with suction. After drying, 3.48 g (82%) of a white powder remained. Melting point 81 C.
	In N-methyl-acetamide; water; ethyl acetate;	EXAMPLE 3 Methyl 2-(4,6-dimethoxy-pyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate 2.86 g (10 mmol) of <strong>[178306-47-3]methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate</strong> were dissolved in 40 ml of dimethylformamide, and 0.3 g (12 mmol) of sodium hydride was added. The mixture was stirred for 1 h. and then 2.2 g (10 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine were added. After stirring at room temperature for 24 h., cautious hydrolysis was carried out with 10 ml of water, the pH was adjusted to 5 with acetic acid, and the solvent was removed by distillation under high vacuum. The residue was taken up in 100 ml of ethyl acetate, washed with water and dried over magnesium sulfate, and the solvent was distilled out. The residue was mixed with 10 ml of ether, and the resulting precipitate was filtered off with suction. After drying, 3.48 g (82%) of a white powder remained.

References: [1]Patent: JP5700378,2015,B2 .Location in patent: Paragraph 0064.
[2]Journal of Medicinal Chemistry,1996,vol. 39,p. 2123 - 2128.
[3]Patent: US5932730,1999,A .
[4]Patent: US6030975,2000,A .

5
4-Ethyl-2-methanesulfonyl-6-methyl-pyrimidine [ No CAS ]
[ 178306-47-3 ]
[ 1026509-86-3 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2123 - 2128.

6
[ 497872-96-5 ]
[ 178306-47-3 ]
[ 1026529-44-1 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2123 - 2128.

7
2-(methylsulfonyl)-4-methoxy-6,7-dihydro-5H-cyclopentapyrimidine [ No CAS ]
[ 178306-47-3 ]
[ 1028291-53-3 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2123 - 2128.

8
4,6-diethoxy-2-(methylsulfonyl)pyrimidine [ No CAS ]
[ 178306-47-3 ]
[ 1026815-03-1 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2123 - 2128.

9
2-(methylsulfonyl)-4-methoxy-5,6-dihydrofuro<2,3-d>pyrimidine [ No CAS ]
[ 178306-47-3 ]
3-Methoxy-2-(4-methoxy-5,6-dihydro-furo[2,3-d]pyrimidin-2-yloxy)-3,3-diphenyl-propionic acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2123 - 2128.

10
[ 178306-47-3 ]
[ 35144-22-0 ]
(S)-methyl-2-(4,6-dimethylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate [ No CAS ]

References: [1]Organic Process Research and Development,2018,vol. 22,p. 1200 - 1207.
[2]Journal of Medicinal Chemistry,1996,vol. 39,p. 2123 - 2128.

11
[ 119-61-9 ]
(+-)-magnesium chloride-<bromomagnesio-(3-chloro-phenyl)-acetate> [ No CAS ]
[ 178306-47-3 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2123 - 2128.

12
[ 178306-47-3 ]
3-Methoxy-2-(4-methyl-pyrimidin-2-yloxy)-3,3-diphenyl-propionic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2123 - 2128.

13
[ 178306-47-3 ]
ambrisentan [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2123 - 2128.
[2]Organic Process Research and Development,2018,vol. 22,p. 1200 - 1207.

14
[ 178306-47-3 ]
2-(4-Ethyl-6-methyl-pyrimidin-2-yloxy)-3-methoxy-3,3-diphenyl-propionic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2123 - 2128.

15
[ 178306-47-3 ]
2-(4,6-Diethyl-pyrimidin-2-yloxy)-3-methoxy-3,3-diphenyl-propionic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2123 - 2128.

16
[ 178306-47-3 ]
3-Methoxy-2-(4-methoxy-6-methyl-pyrimidin-2-yloxy)-3,3-diphenyl-propionic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2123 - 2128.

17
[ 178306-47-3 ]
[ 178306-46-2 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2123 - 2128.
[2]Patent: JP5700378,2015,B2 .

18
[ 178306-47-3 ]
3-methoxy-2-((4-methoxy-6,7-dihydro-5H-cyclopentapyridin-2-yl)oxy)-3,3-diphenylpropanoic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2123 - 2128.

19
[ 178306-47-3 ]
2-(4,6-Diethoxy-pyrimidin-2-yloxy)-3-methoxy-3,3-diphenyl-propionic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2123 - 2128.

20
[ 178306-47-3 ]
3-Methoxy-2-(4-methoxy-5,6-dihydro-furo[2,3-d]pyrimidin-2-yloxy)-3,3-diphenyl-propionic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2123 - 2128.

21
RuO(OH)2 [ No CAS ]
[ 178306-47-3 ]
[ 178306-46-2 ]
2-(4,6-Dimethoxy-2-pyrimidinyloxy)-3-methoxy-3,3-diphenyl sodium [sic] propionate [ No CAS ]
[ 213774-07-3 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; methanol; water; acetic acid;	Example 5 2-(4,6-Dimethoxy-2-pyrimidinyloxy)-3-methoxy-3,3-diphenyl sodium [sic] propionate 1.68 g (4 mmol) of 2-(4,6-dimethoxy-2-pyrimidinyloxy)-3-methoxy-3,3-diphenylpropionic acid are dissolved in 4 ml of 1N NaOH+100 ml of water. The solution is freeze-dried, and the sodium salt of the carboxylic acid used is obtained quantitatively. 10 g (34.9 mmol) of <strong>[178306-47-3]methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate</strong> were dissolved in 50 ml each of methanol and glacial acetic acid, 1 ml of RuO(OH)2 in dioxane was added, and hydrogenation was carried out with H2 in an autoclave at 100 C. under 100 bar for 30 h. The catalyst was filtered off, the mixture was concentrated, mixed with ether and washed with NaCl solution, and the organic phase was dried and concentrated. 10.1 g of methyl 3,3-dicyclohexyl-2-hydroxy-3-methoxypropionate were obtained as an oil.

References: [1]Patent: US5932730,1999,A .

22
[ 76527-25-8 ]
[ 178306-47-3 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroborane diethyl ether; In methanol; ethyl acetate;	Example 1 Methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate 5 g (19.6 mmol) of methyl 3,3-diphenyl-2,3-epoxypropionate were dissolved in 50 ml of absolute methanol and, at 0 C., 0.1 ml of boron trifluoride etherate was added. The mixture was stirred at 0 C. for 2 h and at room temperature for a further 12 h. The solvent was distilled out, the residue was taken up in ethyl acetate, washed with sodium bicarbonate solution and water and dried over magnesium sulfate. After removal of the solvent by distillation there remained 5.5 g (88%) of a pale yellow oil.
	With trifluoroborane diethyl ether; In methanol; ethyl acetate;	EXAMPLE 1 Methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate 5 g (19.6 mmol) of methyl 3,3-diphenyl-2,3-epoxypropionate were dissolved in 50 ml of absolute methanol and, at 0 C., 0.1 ml of boron trifluoride etherate was added. The mixture was stirred at 0 C. for 2 h. and at room temperature for a further 12 h. The solution vent was distilled out, the residue was taken up in ethyl acetate, washed with sodium bicarbonate solution and water and dried over magnesium sulfate. After removal of the solvent by distillation there remained 5.5 g (88%) of a pale yellow oil.
	With trifluoroborane diethyl ether; In methanol; ethyl acetate;	EXAMPLE 1 Methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate 5 g (19.6 mmol) of methyl 3,3-diphenyl-2,3-epoxypropionate were dissolved in 50 ml of absolute methanol, and, at 0 C., 0.1 ml of boron trifluoride etherate was added. The mixture was stirred at 0 C. for 2 h and at room temperature for a further 12 h. The solvent was removed by distillation, the residue was taken up in ethyl acetate, and the solution was washed with sodium bicarbonate solution and water and dried over magnesium sulfate. After removal of the solvent by distillation, 5.5 g (88%) of a pale yellow oil remained.

References: [1]Patent: US5932730,1999,A .
[2]Patent: US6030975,2000,A .
[3]Patent: US6103732,2000,A .
[4]Organic Process Research and Development,2001,vol. 5,p. 16 - 22.

23
[ 124-63-0 ]
[ 178306-47-3 ]
[ 57235-35-5 ]
methyl 2-[(4,6-dimethoxy-pyrimidin-2-yl)thio]-3-methoxy-3,3-diphenylpropionate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; triethylamine; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane; N,N-dimethyl-formamide;	EXAMPLE 7 Methyl 2-(4,6-dimethoxy-pyrimidin-2-ylthio)-3-methoxy-3,3-diphenylpropionate 7.16 g (25 mmol) of <strong>[178306-47-3]methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate</strong> were dissolved in 50 ml of dichloromethane, 3 g (30 mmol) of triethylamine were added, and 3.2 g (28 mmol) of methane-sulfonyl chloride were added dropwise while stirring. The mixture was stirred at room temperature for 2 h., washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was taken up in DMF and added dropwise at 0 C. to a suspension of 12.9 g (75 mmol) of 4,6-dimethoxypyrimidine-2-thiol and 8.4 g (100 mmol) of sodium bicarbonate in 100 ml of DMF. After stirring at room temperature for 2 h. and at 60 C. for a further 2 h., the mixture was poured into 1 liter of ice-water, and the resulting precipitate was filtered off with suction. After drying, 3.19 g (29%) of a white powder remained.

References: [1]Patent: US6030975,2000,A .

24
[ 6320-15-6 ]
[ 178306-47-3 ]
methyl 2-(2,6-dimethoxy-4-pyrimidyloxy)-3-methoxy-3,3-diphenyl-propionate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N-methyl-acetamide; water;	EXAMPLE 2 Methyl 2-(2,6-dimethoxy-4-pyrimidyloxy)-3-methoxy-3,3-diphenyl-propionate 1.15 g (4 mmol) of methyl 2-hydroxy-3-methoxy-3,3-diphenyl-propionate were dissolved in 10 ml of dimethylformamide, and 276 mg (2 mmol) of potassium carbonate were added. Then 524 mg (3 mmol) of 2,6-dimethoxy-4-chloropyrimidine were added, and the mixture was stirred at 100 C. for 6 hours. It was then cautiously hydrolyzed with 10 ml of water, the pH was adjusted to 5 with citric acid and, after extraction with ethyl acetate, the organic phase was washed with water then dried over magnesium sulfate, and the solvent was removed by distillation. The oily residue (1.9 g) was chromatographed on silica gel, resulting in 617 mg of a slightly impure oil.

References: [1]Patent: US6103732,2000,A .

25
RuO(OH)2 [ No CAS ]
[ 178306-47-3 ]
[ 178306-46-2 ]
sodium 2-(4,6-dimethoxy-2-pyrimidinyloxy)-3-methoxy-3,3-diphenyl-propionate [ No CAS ]
[ 213774-07-3 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; methanol; water; acetic acid;	EXAMPLE 5 Sodium 2-(4,6-dimethoxy-2-pyrimidinyloxy)-3-methoxy-3,3-diphenyl-propionate 1.68 g (4 mmol) or 2-(4,6-dimethoxy-2-pyrimidinyloxy)-3-methoxy-3,3-diphenylpropionic acid are dissolved in 4 ml of 1N NaOH+100 ml of water. The solution is freeze-dried, and the sodium salt of the carboxylic acid used is obtained quantitatively. 10 g (34.9 mmol) of <strong>[178306-47-3]methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate</strong> were dissolved in 50 ml each of methanol and glacial acetic acid, 1 ml of RuO(OH)2 in dioxane was added, and hydrogenation was carried out with H2 in an autoclave at 100 C. under 100 bar for 30 h. The catalyst was filtered off, the mixture was concentrated, mixed with ether and washed with NaCl solution, and the organic phase was dried and concentrated. 10.1 g of methyl 3,3-dicyclohexyl-2-hydroxy-3-methoxypropionate were obtained was an oil.

References: [1]Patent: US6030975,2000,A .

26
[ 634-47-9 ]
[ 178306-47-3 ]
methyl 2-(4-methyl-2-quinolinyloxy)-3-methoxy-3,3-diphenyl-propionate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide; water;	EXAMPLE 4 Methyl 2-(4-methyl-2-quinolinyloxy)-3-methoxy-3,3-diphenyl-propionate 5.7 g (20 mmol) of Methyl 2-hydroxy-3-methoxy-3,3-diphenyl-propionate were dissolved in 90 ml of dimethylformamide, and 0.98 g (22 mmol) of sodium hydride (55% in oil) was added. After stirring for 15 minutes, 3.9 g (22 mmol) of 2-chloro-4-methylquinoline were added. The dark red solution was stirred at room temperature overnight, then cautiously hydrolyzed with 20 ml of water and subsequently extracted with ethyl acetate. The organic phase was washed with water, and dried over magnesium sulfate, and the solvent was removed by distillation. The residue (8.1 g) was then chromatographed on silica gel, resulting in 2.6 g of impure product as oil.

References: [1]Patent: US6103732,2000,A .

27
[ 178306-47-3 ]
[ 178306-51-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	With water; sodium hydroxide; at 100℃; for 1h;	500 g (1.75 mol) of (RS) 2-hydroxy-3-methoxy-3,3-diphenyl methyl propanoate Suspended and agitated in 1,000 mL of water, 950 mL (1.90 mol) of 2 mol / L sodium hydroxide was added, and the mixture was stirred at 100 C. for 1 hour. The reaction solution was cooled to room temperature, 1500 mL of tert-butyl methyl ether was added, 700 mL of 10% hydrochloric acid was added, and the mixture was stirred for 20 minutes to dissolve the precipitated solid. After liquid-liquid separation, the organic layer was washed with 1000 mL of water. 1200 mL of heptane was added, and the solvent was distilled off under reduced pressure (200 mmHg) at 40 C. to precipitate crystals. 1000 mL of heptane was added, and the mixture was stirred at 0 C. for 1 hour. The crystals were collected by filtration and dried under reduced pressure at 40 C. for 7 hours,(RS) -2-hydroxy-3-methoxy-3,3-diphenylpropanoic acid 431 g (yield 91%) was obtained.
90%	With water; sodium hydroxide; at 90 - 95℃; for 1.5h;	Step-HI : Preparation of 2-hydroxy-3-methoxy-3,3-diphenyl propionic acid of the formula -(IV) :Into a 5L round bottomed flask a mixture water(l.OL) and compound of formula -III (200g) from step-II were charged and stirred for 15 minutes. IN aqueous sodium hydroxide solution was charged and the reaction mass was stirred for 15 minutes.Reaction mass was heated to 90-95C and maintained at the same temperature for one hour. The reaction mass was brought to room temperature adjustment of pH was carried out with IN hydrochloric acid solution(1.6L) to 2-3. The product slurry was cooled to 5- 10C and maintained at the same temperature for 2hours. The product was filtered and dried at 60-65CDry weight : 172g(90%)Purity by HPLC : 99.88%Melting range : 100- 102 C
		Example-2: Preparation of 2-hydroxy-3-methoxy-3,3-diphenylpropionic acid compound of formula-6:Mixture of <strong>[178306-47-3]2-hydroxy-3-methoxy-3,3-diphenylpropionic acid methyl ester</strong> (100 grams) and aqueous sodium hydroxide solution (22 grams in 200 ml of water) was heated to 95-1000C and stirred for 120 minutes. The reaction mixture was cooled to 40-450C and quenched with water. The pH of the reaction mixture was adjusted to 1.3 with concentrated hydrochloric acid and extracted with ethyl acetate. The solvent from the ethyl acetate layer was distilled off completely under reduced pressure at 600C. The reaction mixture was cooled to 4O0C and cyclohexane (230 ml) was added and stirred at reflux for 30 minutes. The reaction mixture was cooled to.25-35C and stirred for 40 minutes at 25-35C. The solid formed was filtered off and washed with cyclohexane then dried at 60-70C to get the title compound. Yield: 92 grams; M.R: 108-112C

		Preparation of 2-hydroxy-3-methoxy-3,3-diphenylpropionic acid compound of formula-6 Mixture of <strong>[178306-47-3]2-hydroxy-3-methoxy-3,3-diphenylpropionic acid methyl ester</strong> (100 grams) and aqueous sodium hydroxide solution (22 grams in 200 ml of water) was heated to 95-100 C. and stirred for 120 minutes. The reaction mixture was cooled to 40-45 C. and quenched with water. The pH of the reaction mixture was adjusted to 1.3 with concentrated hydrochloric acid and extracted with ethyl acetate. The solvent from the ethyl acetate layer was distilled off completely under reduced pressure at 60 C. The reaction mixture was cooled to 40 C. and cyclohexane (230 ml) was added and stirred at reflux for 30 minutes. The reaction mixture was cooled to 25-35 C. and stirred for 40 minutes at 25-35 C. The solid formed was filtered off and washed with cyclohexane then dried at 60-70 C. to get the title compound.Yield: 92 grams; M.R: 108-112 C.
123 g	With water; sodium hydroxide; In methanol; at 45 - 50℃; for 1h;	140 g of methyl 3,3-diphenyloxirane-2-carboxylate was dissolved in 280 ml of methanol and then cooled to 0C .6.9 ml of BF3OEt2 was added slowly and stirred at 0C for 2 hours. When the methyl 3,3-diphenyloxirane-2-carboxylate disappears completely and <strong>[178306-47-3]methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate</strong> is produced,65.8 g of NaOH was dissolved in 980 ml of water and slowly added dropwise. Methanol (140 ml) was added, the temperature was raised to 45 to 50C, and the mixture was stirred for 1 hour. When the reaction was completed, the methanol was distilled off under reduced pressure, and diluted with 700 ml of dichloromethane. 300 ml of 6N HCl aqueous solution was added to adjust the pH to 2, and the organic layer was separated. The organic layer was washed with 300 ml of brine, dried, filtered and distilled under reduced pressure, and recrystallized from 500 ml of hexane to obtain 123 g of 2-hydroxy-3-methoxy-3,3-diphenylpropionic acid (yield: 82%).

References: [1]Patent: JP2017/128528,2017,A .Location in patent: Paragraph 0005; 0040.
[2]Patent: WO2012/17441,2012,A1 .Location in patent: Page/Page column 11.
[3]Patent: WO2010/70658,2010,A2 .Location in patent: Page/Page column 18-19.
[4]Patent: US2011/263854,2011,A1 .Location in patent: Page/Page column 8.
[5]Organic Process Research and Development,2001,vol. 5,p. 16 - 22.
[6]Patent: KR2016/39907,2016,A .Location in patent: Paragraph 0094; 0095.

28
[ 119-61-9 ]
[ 96-34-4 ]
[ 178306-47-3 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation of 2-hydroxy-3-methoxy-3,3-diphenylpropionic acid methyl ester compound of formula-5a Mixture of benzophenone (100 grams) and methyl chloroacetate (84 grams) in tetrahydrofuran (160 ml) was added to a cooled mixture of tertrahydrofuran and sodium methoxide (51.8 grams) at below -4 C. in 90 minutes, stirred for 30 minutes at -10 C. to -5 C. The reaction mixture temperature was raised to 25-35 C., quenched with water and then extracted with ethyl acetate. The organic layer was washed with brine solution and dried over sodium sulphate. The organic layer was distilled under reduced pressure at 60 C. and methanol was added to the obtained residue then methanol was distilled off completely. The reaction mixture cooled to 25-35 C. and methanol (280 ml) was added to it. Paratoluene sulfonic acid (4 grams) was added to the above reaction mixture. The reaction mixture was stirred for 2 hours at 25-35 C. and then cooled to 0-5 C. and stirred 45 minutes. The obtained solid was filtered, washed with methanol and then dried at 50-60 C. to get the title compound.Yield: 110 grams; M.R: 92-96 C.

References: [1]Patent: US2011/263854,2011,A1 .Location in patent: Page/Page column 7-8.

29
[ 178306-47-3 ]
[ 178306-52-0 ]

References: [1]Patent: US2011/263854,2011,A1 .
[2]Patent: KR2016/39907,2016,A .
[3]Patent: JP2017/128528,2017,A .

30
[ 178306-47-3 ]
[ 177036-78-1 ]

References: [1]Patent: US2011/263854,2011,A1 .
[2]Patent: WO2013/57468,2013,A1 .

31
[ 178306-47-3 ]
ambrisentan [ No CAS ]

References: [1]Patent: US2011/263854,2011,A1 .
[2]Patent: US2011/263854,2011,A1 .
[3]Patent: WO2013/57468,2013,A1 .
[4]Patent: KR2016/39907,2016,A .
[5]Patent: JP2017/128528,2017,A .

32
[ 178306-47-3 ]
[ 171714-84-4 ]

References: [1]Patent: US2011/263854,2011,A1 .
[2]Patent: WO2013/57468,2013,A1 .
[3]Organic Process Research and Development,2001,vol. 5,p. 16 - 22.

33
[ 178306-47-3 ]
[ 1106685-61-3 ]

References: [1]Patent: US2011/263854,2011,A1 .
[2]Patent: WO2013/57468,2013,A1 .

34
[ 178306-47-3 ]
[ 177036-79-2 ]

References: [1]Patent: US2011/263854,2011,A1 .
[2]Patent: WO2013/57468,2013,A1 .

35
[ 178306-47-3 ]
[ 1231755-36-4 ]

References: [1]Patent: US2011/263854,2011,A1 .

Historical Records

Technical Information

• Acyl Group Substitution • Appel Reaction • Bouveault-Blanc Reduction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chugaev Reaction • Complex Metal Hydride Reductions • Corey-Kim Oxidation • Dess-Martin Oxidation • Ester Cleavage • Hydride Reductions • Jones Oxidation • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Nomenclature of Ethers • Oxidation of Alcohols by DMSO • Preparation of Alcohols • Preparation of Amines • Preparation of Ethers • Reactions of Alcohols • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers • Reactions with Organometallic Reagents • Ritter Reaction • Sharpless Olefin Synthesis • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Swern Oxidation

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[ 178306-47-3 ]

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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 178306-47-3

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