147118-40-9|Methyl (3R,5S,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3,5-dihydroxyhept-6-enoate| Ambeed

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Quality Control of [ 147118-40-9 ] Purity: 95% SDS Specification

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Product Details of [ 147118-40-9 ]

CAS No. :	147118-40-9
Formula :	C₂₃H₃₀FN₃O₆S
M.W :	495.56
SMILES Code :	O=C(OC)C[C@H](O)C[C@H](O)/C=C/C1=C(C(C)C)N=C(N(C)S(=O)(C)=O)N=C1C2=CC=C(F)C=C2
MDL No. :	MFCD12756002
InChI Key :	SUTPUCLJAVPJRS-NDZBKKTDSA-N
Pubchem ID :	25183331

Safety of [ 147118-40-9 ]

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

Application In Synthesis of [ 147118-40-9 ]

* 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 [ 147118-40-9 ]

[ 147118-40-9 ] Synthesis Path-Downstream 1~35

1
[ 67-64-1 ]
[ 147118-40-9 ]
[ 851440-19-2 ]

Yield	Reaction Conditions	Operation in experiment
		Example 3 Methyl (E)-(6-[2-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl-(methylsulfonyl)ainino]- rhoyrimidin-5-yl]vmyl](4i?,65)-2,2-dimethyl-[l,3]dioxan-4-yl)-acetate IX; Methyl ester IX (1.07 g) was dissolved in acetone (5.5 ml) and dimethoxypropane (5.5 ml). P- toluenesulfonic acid (0.1 g) was then added, and the mixture was stirred at room temperature for 1.5 hours. Then, alkalization with triethylamine (0.12 ml) was carried out, and the solution was evaporated. After adding ethyl acetate (60 ml), the mixture was shaken with water (2 x 8 ml). The organic layer was dried with Na2SO4 and evaporated. The crude product was crystallized from isopropyl alcohol. 0.88 g of white crystals of acetonide IX was obtained, which were recrystallized from isopropyl alcohol.1H NMR (CDCl3) delta: 7.62 (m, 2H); 7.08 (m, 2H); 6.52 (dd, IH, //=16.21, /2=1.30); 5.45 (dd, IH, //=16.23, J2=5.36); 4.45 (m, IH); 4.35 (m, IH); 3.70 (s, 3H); 3.56 (s, 3H); 3.51 (s, 3H); 3.37 (sept, IH, /=6.68); 2.56 (dd, IH, //=15.68, J2=6.71); 2.38 (dd, IH, //=15.69, /2=6.39); 1.49 (s, 3H); 1.40 (s, 3H); 1.68 (m, IH); 1.27 (d, 3H, J=6.69); 1.23 (d, 3H, J=6.66).

References: [1]Patent: WO2007/121,2007,A1 .Location in patent: Page/Page column 10.

2
[ 1310-73-2 ]
[ 147118-40-9 ]
rosuvastatin sodium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; water; at 25 - 30℃; for 1h;Product distribution / selectivity;	PREPARATION OF ROSUVASTATIN CALCIUM FOLLOWING THE PROCEDURE REPORTED IN THE US PATENT No RE 37,314Ethanolic solution of <strong>[147118-40-9]rosuvastatin methyl ester</strong> (5.53 g in ethanol (78 ml) was treated with aqueous solution of sodium hydroxide (0.1N, 100 ml) at cold temperature and the resulting solution was warmed to 25-30 0C and stirred at this temperature for lhr. Ethanol was evaporated under vacuum at 40-45 0C and the resulting aqueous layer <n="11"/>was washed twice with a mixture of 30percent v/v ethyl acetate/toluene (50 ml). The resulting rosuvastatin sodium solution was concentrated and treated with aqueous solution of calcium chloride (1 N, 10 ml). The resulting mass was stirred for 2 hrs, filtered, washed with DM water and dried under vacuum at 35-40 0C. Dry Wt. 3.2 g, Chromatographic purity (HPLC): 97.05 percent

References: [1]Patent: WO2008/38132,2008,A1 .Location in patent: Page/Page column 9-10.

3
[ 147118-40-9 ]
[ 287714-41-4 ]

Yield	Reaction Conditions	Operation in experiment
		In a round bottom flask 2000 ml Tetrahydrofuran (THF) was added under the nitrogen atmosphere and cooled to -90°C then 1Og sodium borohydride was added followed by 230ml diethylmethoxyborane (1 M solution in THF) in 90-120mins. In this reaction mass, mixture of lOOg of Methyl -7-[4-(4-fiourophenyl)-6-isopropyl-2-(N-methyl-N- methylsulfonylaniino)-pyrimidin-5-yl]-(3R)-3-hydroxy-5-oxo-(E)-6-heptenate5 700 ml THF and 700 ml methanol was added for a duration of 90-120min then stirred for 2 hrs at -90 to -80°C. After the completion of reaction, 124 ml acetic acid was added and stirred for 30-60 min at same temperature. Above reaction mass was diluted with 1500ml ethyl acetate and washed with brine solution. To the organic layer, 500 ml DM water was added and pH was adjusted to neutral by ~ 500 ml 6 percent sodium bicarbonate solution. Both the layers were separated Sc the organic layer was dried over sodium sulphate. The organic layer was concentrated at 40-450C. Above concentrated mass was diluted with 900ml ethyl alcohol and then cooled to 0°C. Sodium hydroxide solution was added in 60- 90 min. The reaction mass was stirred for 30 min at room temperature and the pH was adjusted to 11.5-12.0 by using ~ 4 percent sodium hydroxide solution. In this reaction mass, 1Og activated carbon was added and stirred for 20 min. The reaction mass was filtered and washed with ethanol/DM water mixture. The reaction mass was concentrated up to thick residue at 40-45°C. To this concentrated mass, 500 ml DM water was added followed by 1000ml ethyl acetate and the pH was adjusted to 3.5- 4.0 with 1:4 aqueous hydrochloric acid. Both the layers were separated and the organic layer was washed with brine solution.The organic layer was dried over sodium sulphate and concentrated till dryness at 40-45°C. To the above concentrated mass, 1000 ml acetonitrile was added stirred at room temperature for half an hour. Slowly 20.5 g (S)-2-amino-3, 3 -dimethyl butane was added and stirred for almost 2 hrs. The solid was filtered and washed with acetonitrile and diisopropyl ether. Finally the solid was dried for 6-9 hrs at 40-45°C.Above obtained (S)-2-amino-3, 3 -dimethyl butane salt of rosuvastatin was suspended in 1000 ml isopropanol followed by 100 ml methanol. This reaction mass was heated for half an hour at 60-80°C then stirred for 3-4 hrs at 5-1O0C. The solid was filtered washed with isopropanol and diisopropyl ether. 95 gms of (S)-2-amino-3, 3 -dimethyl butane salt of rosuvastatin was obtained.
		Example 1-4Rosuvastatin free acid solutionRosuvastatin methyl ester (100 g) was dissolved in ethanol (2000 mL) , and while stirring at 0 0C sodium hydroxide aqueous solution (0.1 M, 2000 mL) was added dropwise. After stirring at 0 0C for 30 min, stirring was continued at room temperature for 1 h. The mixture was concentrated to ~ 1000 mL . Isopropyl acetate (2000 mL) was added, and hydrochloric acid (1 M, 200 mL) was added under vigorous stirring. After stirring for 1 h, the phases were separated and the organic phase was dried with azeotropic distillation.
		EXAMPLE 1; PREPARATION OF N,N'-DIBENZYLETHYLENEDIAMINE ROSUVASTATIN SALT; Rosuvastatin methyl ester (1 g) was dissolved in acetonitrile (15 ml) at 25-300C, and cooled to 0-50C. To this cooled solution, aqueous sodium hydroxide (0. IN, 20 ml) was added at 0-50C for 15 min and the temperature of the resulting solution was raised to 25-300C in 1 hr. After completion of the reaction, acetonitrile was evaporated under reduced pressure at 40-450C. The resulting reaction mass was diluted with DM water (15 ml) and washed with 30percent v/v ethyl actetate/toluene (50 ml) at 25-300C. The aqueous layer was treated with an aqueous hydrochloric acid (0.1N, 20 ml) at 0-50C. The resulting solution containing rosuvastatin acid was treated with an aqueous solution of N,N'-dibenzylethylenediamine diacetate (0.9 g in 5 ml DM water) at 24-3O0C and stirred for 2 h for complete precipitation of N5N1- dibenzylethylenediamine rosuvastatin salt. The off-white N5N1- dibenzylethylenediamine rosuvastatin salt was filtered and washed with DM water. This wet salt was slurry washed with ethyl acetate (5 ml) at 25-300C and dried under vacuum at 40-450C. Dry Wt. 0.3 g, Chromatographic purity (HPLC): 99.79, Anti isomer: 0.21percent.1HNMR (DMSO-d6): 1.2 (d, 6H5 J=6.6 Hz, (CHjS)2CH)), 1.39-1.52(m, 2H, CH2CHOH)5 2.19-2.27(m, 2H5 CH2COOH)5 2.6(s, 2H5 CH2NH2+CH2Ar)5 3.46(s, 3H, NCH3), 3.55(s, 3H, CH3SO2N), 3.45(m, IH5 (CH3)2CH), 3.72(s, 2H5 CH2Ar)5 3.82(m, <n="12"/>IH, CHOH), 4.2(m,lH, CHOH), 5.50-5.57( dd, IH, J=16.2 Hz, 5.7Hz, =CHCHOH), 6.5(d, IH, J= 16.2Hz, CH=CHCHOH), 7.25(m, 7H, ArH), 7.72(m, 2H, ArH).

		Tentative Example 3 Preparation of 2-((4/?,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropmethylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimet^^ 4-methylpentan-2-yl ester from N-(4-(4-fluorophenyl)-5-formyl-6- isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide (D) and 2-((4 ?,6S)-6- ((benzo[d]thiazol-2-ylsulfonyl)methyl)-2,2-dimethyl-1 ,3-dioxan-4-yl)acetate 4- methylpentan-2-yl esterThe 4-methylpentan-2-yl ester of compound (5a) with is a radical of formula (D), R3 and R4 are both methyl and R5 is 4-methylpentan-2-yl can be prepared according to the same procedures as outlined in Example 3 starting from 2-((4f?,6S)-6-((benzo[d]thiazol- 2-ylsulfonyl)methyl)-2,2-dimethyl-1 ,3-dioxan-4-yl)acetate 4-methylpentan-2-yl ester instead of the corresponding sec-butyl ester using the same molar amount.For reference purposes 2-((4f?,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N- methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1 ,3-dioxan-4-yl)acetate 4- methylpentan-2-yl ester was prepared from <strong>[147118-40-9]rosuvastatin methyl ester</strong> (EP 521471). Thus, <strong>[147118-40-9]rosuvastatin methyl ester</strong> (30 g, 61 mmol) was added to 200 mL of acetonitrile and 2N aqueous NaOH was added until the pH was stable at 12.5. The reaction mixture was stirred for 2 h at 20°C. Then the pH was lowered to 5.0 with 2N aqueous HCI. To the reaction mixture was added 200 mL of ethyl acetate and the organic phase was separated and washed 2 times with 100 mL of water. The ethyl acetate phase was dried over Na2S04, filtered and evaporated to a sirup (" 30 g of rosuvastatin acid). Part of this sirup (20 g) was dissolved in toluene and heated to reflux under azeotropic water removal for 4 h. The reaction mixture was cooled to 20°C and stirred for 18h. The precipitated solid was filtered, washed with toluene (2 x 10 mL) and dried to give 16.1 g (35 m mol) of N-(4-(4-fluorophenyl)-5-((E)-2-((2S,4 )-4-hydroxy-6-oxotetrahydro-2H- pyran-2-yl)vinyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide as a white solid. 1 H NMR (300 MHz, CDCI3) delta 7.62 (dd, 2H), 7.1 1 (dd, 2H), 6.72 (dd, 1 H), 5.48 (dd, 1 H), 5.28-5.20 (m, 1 H), 4.38-4.30 (m, 1 H), 3.58 (s, 3H), 3.52 (s, 3H), 3.38-3.30 (m, 1 H), 2.80-2.60 (m, 2H), 2.10-2.00 (m, 1 H), 1 .95-1 .85 (m, 1 H), 1 .73-1.68 (m, 1 H), 1 .28 (d, 3H), 1.26 (d, 3H). Of this compound, 2.3 g (5.0 mmol) was added to 25 mL of 2-(4-methyl)-pentanol. Then 2 drops of methanesulphonic acid were added and the reaction mixture was heated to 60°C and stirred for 1 h. The reaction mixture was cooled to 20°C and stirred for 18h. Next 2,2-dimethoxypropane (0.78 g, 7.5 mol) was added and the mixture was stirred for 2h. The reaction mixture was quenched with 20 mL of saturated aqueous NaHC03 followed by addition of 25 mL of ethyl acetate. The organic phase was separated and washed 2 times with 20 mL of saturated aqueous NaHC03 The organic phase was evaporated and the residue slowly solidified to give the title compound as a solid (2.9 g, 96percent yield). 1 H NMR (300 MHz, CDCI3) delta 7.58 (dd, 2H), 7.01 (t, 2H), 6.46 (dd, 1 H), 5.42 (dd, 1 H), 4.87 (m, 1 H), 4.43 - 4.20 (m, 2H), 3.50 (s, 3H), 3.45 (s, 3H), 3.35 - 3.25 (m, 1 H), 2.38 (ddd, 2H), 1.59 - 1.43 (m, 4H), 1.40 (s, 3H), 1.35 (s, 3H), 1.20, (dd, 4 H), 1.14 (d, 6H), 0.83 (t, 6H).
		For reference purposes 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate 4-methylpentan-2-yl ester was prepared from <strong>[147118-40-9]rosuvastatin methyl ester</strong> (EP 521471). Thus, <strong>[147118-40-9]rosuvastatin methyl ester</strong> (30 g, 61 mmol) was added to 200 mL of acetonitrile and 2N aqueous NaOH was added until the pH was stable at 12.5. The reaction mixture was stirred for 2 h at 20° C. Then the pH was lowered to 5.0 with 2N aqueous HCl. To the reaction mixture was added 200 mL of ethyl acetate and the organic phase was separated and washed 2 times with 100 mL of water. The ethyl acetate phase was dried over Na2SO4, filtered and evaporated to a sirup (?30 g of rosuvastatin acid). Part of this sirup (20 g) was dissolved in toluene and heated to reflux under azeotropic water removal for 4 h. The reaction mixture was cooled to 20° C. and stirred for 18 h. The precipitated solid was filtered, washed with toluene (2×10 mL) and dried to give 16.1 g (35 m mol) of N-(4-(4-fluorophenyl)-5-((E)-2-((2S,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)vinyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide as a white solid. 1H NMR (300 MHz, CDCl3) delta 7.62 (dd, 2H), 7.11 (dd, 2H), 6.72 (dd, 1H), 5.48 (dd, 1H), 5.28-5.20 (m, 1H), 4.38-4.30 (m, 1H), 3.58 (s, 3H), 3.52 (s, 3H), 3.38-3.30 (m, 1H), 2.80-2.60 (m, 2H), 2.10-2.00 (m, 1H), 1.95-1.85 (m, 1H), 1.73-1.68 (m, 1H), 1.28 (d, 3H), 1.26 (d, 3H).

References: [1]Patent: WO2010/35284,2010,A2 .Location in patent: Page/Page column 9.
[2]Patent: WO2010/81861,2010,A1 .Location in patent: Page/Page column 42.
[3]Patent: WO2008/38132,2008,A1 .Location in patent: Page/Page column 10-11.
[4]Patent: EP2298745,2011,A1 .
[5]Patent: WO2012/98049,2012,A1 .Location in patent: Page/Page column 16-17.
[6]Patent: US2013/296561,2013,A1 .Location in patent: Paragraph 0041.

4
[ 459-57-4 ]
PhCH₂CH₂MgHal [ No CAS ]
[ 147118-40-9 ]