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[ CAS No. 189028-93-1 ] {[proInfo.proName]}

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Chemical Structure| 189028-93-1
Chemical Structure| 189028-93-1
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Product Details of [ 189028-93-1 ]

CAS No. :189028-93-1 MDL No. :MFCD08061377
Formula : C20H18FNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :XXSSRSVXDNUAQX-QGZVFWFLSA-N
M.W : 355.36 Pubchem ID :11187377
Synonyms :

Safety of [ 189028-93-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 189028-93-1 ]

* 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 [ 189028-93-1 ]

[ 189028-93-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 3282-30-2 ]
  • [ 149437-76-3 ]
  • [ 186343-35-1 ]
  • [ 189028-93-1 ]
YieldReaction ConditionsOperation in experiment
85.7% Step 1A. Preparation of (4S)-4-phenyl-3-[5-(4-fluorophenyl)-5-oxopentanoyl]-1,3 -oxazolidin-2-one (A1 R6=phenyl); 5-(4-Fluorophenyl)-5-oxopentanoic acid (21.02 g, 100.0 mmol) and 4 dimethylamino-pyridine (16.25 g, 133.0 mmol) were dissolved in N,N-dimethylformamide (100 mL, 1.0 M) to afford a copious white precipitate suspended in solution. The reaction was cooled to 2 C. (ice/water bath), and trimethylacetyl chloride (16.40 mL, 16.04 g, 133.0 mmol) was added drop-wise to afford a pale yellow mixture. The rate of addition was controlled in order to keep the temperature at or below 5 C. A heavy white precipitate was formed and the mixture was allowed to warm to room temperature and stirred for 1.5 h. The mixture was charged with (s)-(+)-4-phenyl-2-oxazolidinone (16.32 g, 100.0 mmol) and 4-dimethylaminopyridine (12.22 g, 100.0 mmol) both as solids to afford a yellow colored suspension. The reaction was stirred at 30 C. -35 C. for 2 h. An aliquot was removed for analysis by TLC and HPLC. The pale olive colored suspension was poured into water (400 mL) while stirring vigorously and cooling the mixture in an ice-brine bath, transferred with water (150 mL) and stirred with ice-cooling for 1.5 h to afford a solution with an off-white precipitate. The compound was filtered, transferred with water (2×25 mL), washed with water (50 mL) and air dried for 15 min to afford an off-white moist clumpy powder. The material was crystallized from isopropanol (58.0 mL; 1.6 mL/g theoretical yield) by heating to near reflux to afford a golden yellow colored solution. The solution was cooled slowly to room temperature over 12 h, a seed crystal was added and crystals began to precipitate. The mixture was cooled in an ice/water bath and stirred for 1 h. The crystals were filtered, transferred with cold isopropanol (2×10 mL), washed with cold isopropanol (25 mL), air dried and vacuum dried to constant weight to afford (4S)-4-phenyl-3-[5-(4-fluorophenyl)-5-oxopentanoyl]-1,3-oxazolidin-2-one (30.46 g, 85.7% yield) as a white crystalline solid; m.p. 91.0 C.; Rf 0.40 (1:2 ethyl acetate-hexane); HPLC RT 7.02 min; HPLC purity 94%. 1H NMR (300 MHz, CDCl3) delta 7.93 (dd, J=5.4, 9.0 Hz, 2H), 7.28-7.42 (m, 5H), 7.10 (dd, J=8.5, 9.0 Hz, 2H), 5.43 (dd, J=3.7, 8.7 Hz, 1H), 4.70 (t, J=8.9 Hz, 1H), 4.28 (dd, J=3.7, 8.7 Hz, 1H), 3.05 (dt, J=1.2, 7.3 Hz, 2H), 2.97 (t, J=7.3, 2H), 2.05 (p, J=7.3 Hz, 2H), ppm.
  • 2
  • [ 99395-88-7 ]
  • [ 149437-76-3 ]
  • [ 189028-93-1 ]
YieldReaction ConditionsOperation in experiment
86% With dmap; dicyclohexyl-carbodiimide; In dichloromethane; Example 1: Preparation of ezetimibe; (1-1) Preparation of 3-[5-(fluorophenyl)-l,5-dioxapentyl]-4(S)- phenyl-2-oxazolidinone (Formula 7); 200 g of <strong>[149437-76-3]5-(4-fluorophenyl)-5-oxopentanoic acid</strong> of formula 8, 16O g of (S)-4-phenyloxazolidine-2-one of formula 9, and 11.6 g of 4-dimethylaminopyridine were dissolved in 600 m£ of dichloromethane to prepare a reaction mixture. A solution which was prepared by dissolving 157 g of N,N'-dicyclohexylcarboimide in 200 ml of dichloromethane was added to the reaction mixture and stirred for 2 hours. After completion of the reaction, the resulting reaction mixture was filtered to remove by-products. The filtrate thus obtained was washed successively with 1 I of 6N HCl, 1 ? of water, and 1 ? of saturated sodium chloride, dried over anhydrous magnesium sulfate, filtered, and distilled under a reduced pressure to remove the solvent. The residue thus obtained was dissolved in 2 I of methanol by heating and cooled to induce crystallization. 2 £ of water was added thereto and stirred for 30 min. The solid thus obtained was isolated by filtering to obtain 289 g of the title compound as a white solid (yield: 86%).1H NMR(300MHz, CDCl3) : delta 7.92 (2H, M), 7.35-7.13 (5H, m), 7.04 (2H, m), 5.43 (IH, q), 4.75(1H, t), 4.22 (IH, q), 3.05-2.93 (4H, m), 2.03 (2H, m)
85.7% 5-(4-Fluorophenyl)-5-oxopentanoic acid (21.02 g, 100.0 mmol) and 4 dimethylamino- pyridine (16.25 g, 133.0 mmol) were dissolved in N,N-dimethylformamide (100 mL, 1.0 M) to afford a copious white precipitate suspended in solution. The reaction was cooled to 2 0C (ice/water bath), and trimethylacetyl chloride (16.40 mL, 16.04 g, 133.0 mmol) was added drop-wise to afford a pale yellow mixture. The rate of addition was controlled in order to keep the temperature at or below 5 0C. A heavy white precipitate was formed and the mixture was allowed to warm to room temperature and stirred for 1.5 h. The mixture was charged with (6)-(+)-4-phenyl-2- oxazolidinone (16.32 g, 100.0 mmol) and 4-dimethylaminopyridine (12.22 g, 100.0 mmol) both as solids to afford a yellow colored suspension. The reaction was stirred at 30 C - 35 0C for 2 h. An aliquot was removed for analysis by TLC and HPLC. The pale olive colored suspension was poured into water (400 mL) while stirring vigorously and cooling the mixture in an ice-brine bath, transferred with water (150 mL) and stirred with ice-cooling for 1.5 h to afford a solution with an off-white precipitate. The compound was filtered, transferred with water (2 x 25 mL), washed with water (50 mL) and air dried for 15 min to afford an off-white moist clumpy powder. The material was crystallized from isopropanol (58.0 mL; 1.6 mL/g theoretical yield) by heating to near reflux to afford a golden yellow colored solution. The solution was cooled slowly to room temperature over 12 h, a seed crystal was added and crystals began to precipitate. The mixture was cooled in an ice/water bath and stirred for 1 h. The crystals were filtered, transferred with cold isopropanol (2 x 10 mL), washed with cold isopropanol (25 mL), air dried and vacuum dried to constant weight to afford (45)-4-phenyl-3-[5-(4-fluorophenyl)-5-oxopentanoyl]-l,3- oxazolidin-2-one (30.46 g, 85.7 % yield) as a white crystalline solid; m.p. 91.0 0C; EPO <DP n="43"/>R/ 0.40 (1:2 ethyl acetate-hexane); HPLC Rr7.02 min; HPLC purity 94 %. 1H NMR (300 MHz, CDCl3) delta 7.93 (dd, J= 5.4, 9.0 Hz, 2H), 7.28-7.42 (m, 5H), 7.10 (dd, J= 8.5, 9.0 Hz, 2H), 5.43 (dd, J= 3.7, 8.7 Hz, IH), 4.70 (t, J= 8.9 Hz, IH), 4.28 (dd, J= 3.7, 8.7 Hz, IH), 3.05 (dt, J= 1.2, 7.3 Hz, 2H), 2.97 (t, J= 7.3, 2H), 2.05 (p, J= 7.3 Hz, 2H), ppm.
85% To the soulution of compound 2 (700 g, 3.33 mol, 1.1 eq) dissolved in THF (5 L) was added triethylamine (1.2 L, 7.87 mol, 2.6 eq) at room temperature under N2 atmosphere. Then the solution of pivalic acid chloride (400 g, 3.33 mol, 1.1 eq) in THF (700 mL) was added dropwise to the reaction mixture cooled to -10 C for about 2 h. After addition, the mixture was stirred for 2 h at this temperature. TLC showed the compound 2 was consumed up, then the Evans auxiliary (493.5 g, 3 mol, 1 eq) and anhydrous LiCl (150.5 g, 3.5 mol,1.17 eq) were added sequencely. The mixture was warmed to room temperature and stirred for 2 h till the anhydride intermediate was consumed up. Then ethylacetate (2 L) and NH4Cl aq (1 L) were added, stirred for 15 min, stayed and separated, the aqueous layer was extracted with ethyl acetate (500 mL×2), combined the organic phase, washed with water (250 mL ×2), concentrated.The residue was recrystallized from isopropanol (7 L) to afforded compound 4 as a white solid (913.6 g, 85.0% yield). HPLC purity: 99.2%, mp: 94-95 C [lit.9(b) 91C]. 1H-NMR (CDCl3,400 MHz): delta 7.94-7.93 (m, 2H, J=2), 7.40-7.29 (m, 5H), 7.10-7.01 (m, 2H), 5.45-5.41 (m, 1H), 4.72-4.63 (m, 1H), 4.30-4.27 (m, 1H), 3.06 (t, 2H, J=8), 2.97 (t, 2H, J=12), 2.10-2.03 (m, 2H). 13C-NMR (CDCl3, 100MHz): delta 197.7, 172.2, 167.0, 164.4, 153.8, 139.2, 133.3, 130.7, 130.6, 129.2, 128.7, 126.0, 115.7, 115.5, 70.1, 57.6, 37.3, 34.8, 18.5. MS (ESI) m/z calcd. for C20H18FNO4: 355.12, calcd. for C20H18FNO4Na (M+Na)=378.12, found 378.04 (M+Na).
70% Compound I (21 g, 0.1 mol) was added to a 500 ml three-necked flask, Triethylamine 20 ml and dichloromethane 250 ml, Stuttgart dropwise pivaloyl chloride (14.4g, 0.12mol), (4S) -4-phenyl-2-oxazolidinone (24.5 g, 0.15 mol), DMF 5 ml, 4,4-dimethylaminopyridine (1.22 g, 0.01 mol) was added after refluxing for 3 h, After refluxing for 10 h, Ice bath cooling, Then, 200 ml of 5 M hydrochloric acid was added dropwise at 0 C, Static stratification, The lower methylene chloride layer was washed successively with saturated sodium bicarbonate solution and water, Dried over anhydrous sodium sulfate. The filtrate was concentrated to dryness, To give 24.9 g of a white solid compound II, Yield 70%.
68% The compound (4) (30 g, 142.72 mmol) Triethylamine (26 g, 256.91 mmol) was dissolved in dichloromethane (150 ml)Cooling to 5 to 10 C, dropwise addition of pivaloyl chloride (17.3g, 142.62mmol), System has exothermic, 30min drop finished,5 to 10 deg C insulation reaction 2h, To the reaction system was added (S) -4-phenyl-2-oxazolidinone (23.3 g, 142.76 mmol) DMAP (2.4 g, 19.63 mmol), DMF (15 ml),Exothermic The temperature rose to 15 C, Heated to 45 reflux reaction 3h, Down to room temperature, Plus dichloromethane (150 ml), The organic phase was washed with water (60 ml) 1N hydrochloric acid (120 ml) Water (60ml) 2.5% aqueous sodium hydroxide solution (180 ml) Add water (50ml) wash, Organic phase concentrated dry, Plus isopropyl alcohol (60 ml), Stirring for 24 h, Filter, Add isopropyl alcohol (10ml) leaching, To give a white solid, I.e. compound (5) (34.4 g, 68% yield).

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