[ CAS No. 90319-52-1 ] {[proInfo.proName]}

Name: 90319-52-1|(R)-4-Phenyloxazolidin-2-one|97%
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SKU: A155508
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Quality Control of [ 90319-52-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 90319-52-1 ]

SDS Specification

Alternatived Products of [ 90319-52-1 ]

Product Details of [ 90319-52-1 ]

CAS No. :	90319-52-1	MDL No. :	MFCD00192393
Formula :	C₉H₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QDMNNMIOWVJVLY-QMMMGPOBSA-N
M.W :	163.17	Pubchem ID :	730425
Synonyms :

Calculated chemistry of [ 90319-52-1 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	47.3
TPSA :	38.33 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.41 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.51
Log Po/w (XLOGP3) :	1.25
Log Po/w (WLOGP) :	0.76
Log Po/w (MLOGP) :	1.12
Log Po/w (SILICOS-IT) :	1.6
Consensus Log Po/w :	1.25

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.94
Solubility :	1.86 mg/ml ; 0.0114 mol/l
Class :	Very soluble
Log S (Ali) :	-1.65
Solubility :	3.63 mg/ml ; 0.0222 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.67
Solubility :	0.35 mg/ml ; 0.00215 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.04

Safety of [ 90319-52-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 90319-52-1 ]

* 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.

Upstream synthesis route of [ 90319-52-1 ]
Downstream synthetic route of [ 90319-52-1 ]

[ 90319-52-1 ] Synthesis Path-Upstream 1~7

1
[ 79-03-8 ]
[ 90319-52-1 ]
[ 160695-26-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With dmap; triethylamine In dichloromethane at 0℃; for 1 h;	(R) -4-phenyl-2-oxazolidinone (16.3 g,1 eq.) Was dissolved in 180 ml of dichloromethane,A mixture of triethylamine (15.2 g, 1.5 equiv) was added with stirring at 0 ° C,4-dimethylaminopyridine (DMAP) (366 mg, 0.03 equiv)Subsequently, propionyl chloride (9.2 g, 1 equivalent) was added dropwise, and the mixture was stirred at 0 ° C for 1 hour,Add methylene chloride diluted, washed with water, saturated sodium bicarbonate,The organic phase was dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure,Get the crude product. The crude product was purified by column chromatography,To give the title compound (III-a) (20.1 g, yield 92percent).

Reference： [1] Organic Letters, 2011, vol. 13, # 21, p. 5762 - 5765
[2] Patent: CN105085322, 2017, B, . Location in patent: Paragraph 0065; 0066; 0067; 0068
[3] Organic Process Research and Development, 2005, vol. 9, # 6, p. 827 - 829
[4] Advanced Synthesis and Catalysis, 2018, vol. 360, # 5, p. 965 - 971

2
[ 124-38-9 ]
[ 201300-96-1 ]
[ 90319-52-1 ]
[ 160695-26-1 ]

Reference： [1] Organic Letters, 2002, vol. 4, # 16, p. 2617 - 2620
[2] Organic Letters, 2002, vol. 4, # 16, p. 2617 - 2620
[3] Journal of Organic Chemistry, 2004, vol. 69, # 2, p. 487 - 494

3
[ 90319-52-1 ]
[ 123-62-6 ]
[ 160695-26-1 ]

Reference： [1] Journal of Organic Chemistry, 2001, vol. 66, # 18, p. 6185 - 6188
[2] Organic Letters, 2013, vol. 15, # 3, p. 472 - 475

4
[ 90319-52-1 ]
[ 802294-64-0 ]
[ 160695-26-1 ]

Yield	Reaction Conditions	Operation in experiment
124 g	With dmap; dicyclohexyl-carbodiimide In toluene at 0 - 30℃; for 15 h;	Example-20: Preparation of (R)-4-phenyI-3-propionyIoxazolidin-2-one (Formula B-I) ( )-4-phenyloxazolidin-2-one (100 gm) and dimethylaminopyridine (10 gm) were added to a mixture of propionic acid (50 gm) and toluene (400 ml) at 25-30°C. Cooled the reaction mixture to 0-5°C, dicyclohexylcarbodiimide (151.5 gm) was slowly added and stirred the reaction mixture for 1 hr at the same temperature. Slowly raised the temperature of the reaction mixture to 25-30°C and stirred for 14 hrs at the same temperature. Filtered the reaction mixture, aqueous hydrochloric acid solution was added to the filtrate and stirred the reaction mixture for 20 min at the same temperature. Both the organic and aqueous layers were separated and washed the organic layer with aqueous HC1 solution followed by with aqueous sodium bicarbonate solution and then with aqueous sodium chloride solution. Distilled off the solvent completely from the organic layer under reduced pressure and co- distilled with cyclohexane under reduced pressure. Cyclohexane (200 ml) was added to the obtained solid at 55-60°C and stirred for 15 min at the same temperature. Cooled the reaction mixture to 25-30°C and stirred for 40 min at the same temperature. Filtered the solid, washed with cyclohexane and dried to get the title compound. Yield: 124.0 gm. M.R: 81-82°C.

Reference： [1] Patent: WO2015/87351, 2015, A2, . Location in patent: Page/Page column 48-49

5
[ 86217-38-1 ]
[ 123-62-6 ]
[ 90319-52-1 ]
[ 99395-88-7 ]
[ 160695-26-1 ]
[ 184363-66-4 ]

Reference： [1] Journal of the American Chemical Society, 2006, vol. 128, # 20, p. 6536 - 6537

6
[ 86217-38-1 ]
[ 123-62-6 ]
[ 90319-52-1 ]
[ 99395-88-7 ]
[ 160695-26-1 ]
[ 184363-66-4 ]

Reference： [1] Journal of the American Chemical Society, 2006, vol. 128, # 20, p. 6536 - 6537

7
[ 90319-52-1 ]
[ 123-62-6 ]
[ 184363-66-4 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 3, p. 472 - 475

[ 90319-52-1 ] Synthesis Path-Downstream 1~72

1
[ 625-35-4 ]
[ 90319-52-1 ]
[ 148766-15-8 ]

Yield	Reaction Conditions	Operation in experiment
68%		Synthesis of (R,E)-3-but-2-enoyl-4-phenyloxazolidin-2-one:To a solution of (R)-4-phenyloxazolidin-2-one (8.30 g, 50.9 mmol) in anhydrous THF (80 mL) were added LiCI (2.48 g, 58.5 mmol) and triethylamine (10.30 g, 101.8 mmol). The resulting solution was stirred at RT for 20 minutes, and was then cooled by an ice- water bath. DMAP (0.63 g, 5.1 mmol) was added followed by drop-wise addition of (E)- but-2-enoyl chloride (6.11 g, 58.5 mmol). The resulting yellow suspension was stirred at 0 °C for 0.5 h, then at RT for 16 h. Water (160 mL) was added to quench the reaction, and the mixture was extracted with EtOAc (1 x 150 mL, 2 x 100 mL). The combined organic phases were washed with brine (50 mL), dried over magnesium sulfate. The solvent was removed under reduced pressure to give crude product as yellowish oily wax, which was purified by chromatography (0 - 50percent EtO Ac/heptane) to obtain (R,E)-3-but- 2-enoyl-4-phenyloxazolidin-2-one as light yellow wax (8.0 g, 68percent). 1H NMR (300 MHz, CDCI3/TMS): delta 7.50-7.20 (m, 6H), 7.18-7.00 (m, 1H), 5.48 (dd, 1H, J = 8.7, 3.9 Hz), 4.69 (t, 1H, J= 8.7 Hz), 4.27 (dd, 1H, J= 8.7, 3.9 Hz), 1.93 (dd, 3H, J= 6.7, 1.3 Hz); 13C NMR (75 MHz, CDCI3/TMS): delta 164.2, 153.5, 146.9, 138.9, 128.9, 128.3, 125.7, 121.5, 69.8, 57.6, 18.5.
68%		[0791] Synthesis of (R,E)-3-but-2-enoyl-4-phenyloxazolidin-2-one: [0792] To a solution of (R)-4-phenyloxazolidin-2-one (8.30 g, 50.9 mmol) in anhydrous THF (80 mL) were added LiCI (2.48 g, 58.5 mmol) and triethylamine (10.30 g, 101.8 mmol). The resulting solution was stirred at RT for 20 minutes, and was then cooled by an ice-water bath. DMAP (0.63 g, 5.1 mmol) was added followed by drop-wise addition of (E)-but-2-enoyl chloride (6.11 g, 58.5 mmol). The resulting yellow suspension was stirred at 0 °C for 0.5 h, then at RT for 16 h. Water (160 mL) was added to quench the reaction, and the mixture was extracted with EtOAc (1 x 150 mL, 2 x 100 mL). The combined organic phases were washed with brine (50 mL), dried over magnesium sulfate. The solvent was removed under reduced pressure to give crude product as yellowish oily wax, which was purified by chromatography (0 - 50percent EtO Ac/heptane) to obtain (R,E)-3-but-2-enoyl-4-phenyloxazolidin-2-one as light yellow wax (8.0 g, 68percent). 1H NMR (300 MHz, CDC13/TMS): delta 7.50-7.20 (m, 6H), 7.18-7.00 (m, 1H), 5.48 (dd, 1H, J= 8.7, 3.9 Hz), 4.69 (t, 1H, J= 8.7 Hz), 4.27 (dd, 1H, J= 8.7, 3.9 Hz), 1.93 (dd, 3H, J= 6.7, 1.3 Hz); 13C NMR (75 MHz, CDCI3/TMS): delta 164.2, 153.5, 146.9, 138.9, 128.9, 128.3, 125.7, 121.5, 69.8, 57.6, 18.5.

Reference： [1]Tetrahedron,2004,vol. 60,p. 2097 - 2110
[2]Patent: WO2012/40230,2012,A1 .Location in patent: Page/Page column 103
[3]Patent: WO2013/142269,2013,A1 .Location in patent: Paragraph 0791; 0792
[4]Journal of Organic Chemistry,1993,vol. 58,p. 7565 - 7571

2
[ 124-38-9 ]
[ 56613-80-0 ]
[ 90319-52-1 ]

Yield	Reaction Conditions	Operation in experiment
69%	With caesium carbonate; In dimethylsulfoxide-d6; at 25 - 150℃; under 3800.26 Torr; for 24h;Schlenk technique; Autoclave;	General procedure: To a DMSO-d6 (1 mL) solution of cesium carbonate (33 mg, 0.1 mmol) in a Teflon tube was added (S)-1b (78 muL, 1 mmol). The Teflon tube containing the reaction mixture was fitted into a 30 mL autoclave. The autoclave was frozen with liquid nitrogen (?196 °C) prior to connecting to a vacuum line for air removal. After the mixture was evaporated under vacuum at ?196 °C and warmed up to room temperature, CO2 was filled into the autoclave (3 atm). The autoclave was stirred at 150 °C for 24 h. Upon completion, the reaction mixture was subjected to 1H NMR for crude product yield determination, which calculated based on the ratio between product and internal standard (N,N-dimethylformamide). After that, DMSO-d6 was removed through distillation under vacuum conditions; the syrupy product was then purified by column chromatography on silica gel (hexane/ethyl acetate 3:1) to give the product (S)-4-methyloxazolidin-2-one (S)-2b as colorless oil with an isolated yield of 36percent (36.4 mg, 0.36 mmol).

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 4759 - 4761
[2]Journal of Organic Chemistry,2010,vol. 75,p. 3037 - 3046
[3]Synlett,2009,p. 395 - 398
[4]Tetrahedron Letters,2013,vol. 54,p. 4717 - 4720
[5]Journal of the Chemical Society. Perkin transactions I,1993,p. 5 - 6

3
[ 90319-52-1 ]
[ 112459-65-1 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 1238
[2]Tetrahedron Letters,1984,vol. 25,p. 4071 - 4074

4
[ 90319-52-1 ]
[ 102-92-1 ]
[ 155835-37-3 ]

Yield	Reaction Conditions	Operation in experiment
99.9%		Preparation of (i?)-3-cinnamoyl-4-phenyloxazolidin-2-one: A THF (50 mL) solution of (i?)-4-phenyloxazolidin-2-one (5.90 g, 36.2 mmol) was cooled to -78 °C and treated with lithium bis(trimethylsilyl)amide (36.9 mL, 36.9 mmol, 1.0 M in THF) dropwise over 15 minutes. After 15-minute stirring at -78 °C, a THF (10 mL) solution of cinnamoyl chloride (6.33 g, 38.0 mmol) was then introduced. The mixture was stirred for 1 hour at -78 °C and 2 hours at ambient temperature before it was quenched with saturated NaHCC>3 (50 mL) and stirred for 1 hour. The mixture was diluted with EtOAc (200 mL), washed with water and brine, dried over MgS04, filtered and concentrated to give the product as a pale yellow solid (10.6 g, 99.9percent yield). MS (apci) m/z = 293.9 (M+H).
0.28 g		General procedure: n-Butyllithium (1.15mL, 1.0equiv, 2.3M in hexanes) was added to a cooled until ?75°C solution of the corresponding oxazolidinone (2.6mmol) in anhydrous THF (12mL), then the resulting solution was warmed to ?30°C and stirred for 20min. At the same temperature, a solution of cinnamoyl chloride (1.0equiv) in anhydrous THF (7mL) was added dropwise and then allowed to rise to at room temperature and left overnight with continuous stirring. After work-up with 10percent NH4Cl (15mL), the organic layer was separated and the aqueous layer was extracted with ethyl acetate (2×25ml). The combined organic phase was dried over Na2SO4, filtered and evaporated under reduced pressure. The crude products were purified by chromatography or crystallized from appropriate solvents. 4.3.1 (R)-4-Phenyl-3-[(E)-(3-phenylacryloyl)]-oxazolidin-2-one 2a. White crystals (0.28g, 62percent yield) after crystallization (Et2O/EtOAc, 1:1); mp 169?170°C. 1H NMR (200MHz, CDCl3) delta 4.32 (dd, J=3.8, 8.8Hz, 1H, NCHCH2), 4.74 (t, J=8.8Hz, 1H, NCHCH2), 5.56 (dd, J=3.8, 8.8Hz, 1H, NCHCH2), 7.28?7.48 (m, 8H, aromH), 7.52?7.66 (m, 2H, aromH), 7.78 (d, J=15.7Hz, 1H, CH=CH?CO), 7.95 (d, J=15.7Hz, 1H, CH=CH?CO). 13C NMR (75MHz, CDCl3) delta 58.0, 70.1, 117.0, 126.1, 128.7, 128.8, 129.0, 129.3, 130.8, 134.6, 139.2, 146.8, 153.9, 164.9

Reference： [1]Patent: WO2012/158413,2012,A2 .Location in patent: Page/Page column 81
[2]Helvetica Chimica Acta,2002,vol. 85,p. 3616 - 3623
[3]Journal of Organic Chemistry,2002,vol. 67,p. 1719 - 1721
[4]Tetrahedron,2004,vol. 60,p. 2097 - 2110
[5]Russian Chemical Bulletin,1996,vol. 45,p. 600 - 609
[6]Journal of Organic Chemistry,2001,vol. 66,p. 6185 - 6188
[7]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 2388 - 2399
[8]Tetrahedron Asymmetry,2016,vol. 27,p. 843 - 851

5
[ 17126-67-9 ]
[ 90319-52-1 ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 2742 - 2748

6
[ 201230-82-2 ]
[ 56613-80-0 ]
[ 90319-52-1 ]

Reference： [1]Organic Letters,2000,vol. 2,p. 625 - 626
[2]Journal of Organic Chemistry,2003,vol. 68,p. 601 - 604
[3]Journal of Organic Chemistry,2006,vol. 71,p. 5951 - 5958
[4]ChemSusChem,2015,vol. 8,p. 2204 - 2211
[5]Tetrahedron Letters,2001,vol. 42,p. 3451 - 3453
[6]Tetrahedron Letters,2001,vol. 42,p. 3451 - 3453
[7]Organic Process Research and Development,2017,vol. 21,p. 1080 - 1087

7
[ 616-45-5 ]
[ 1518-06-5 ]
[ 90319-52-1 ]
(R)-(-)-N-(3-methylbut-2-enoyl)-4-phenyloxazolidin-2-one [ No CAS ]
N-(3-methylbut-2-enoyl)-2-pyrrolidone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 63% 2: 15%	With tetraethylammonium perchlorate In acetonitrile at 20℃; Electrochemical reaction;

Reference： [1]Feroci, Marta; Inesi, Achille; Rossi, Leucio; Sotgiu, Giovanni [European Journal of Organic Chemistry, 2001, # 14, p. 2765 - 2769]

8
[ 90319-52-1 ]
[ 123-62-6 ]
[ 160695-26-1 ]

Yield	Reaction Conditions	Operation in experiment
89%		General procedure: To a solution of 15a (19.0 g, 107 mmol) in THF (300 mL) cooled to -78 C was added n-butyllithium (47.2 mL, 118 mmol, 2.5 M solution in hexane) dropwise. The resulting solution was stirred at this temperature for 20 min before the dropwise addition of propionic anhydride (15.1 mL, 118 mmol). The cooling bath was removed, and the flask was allowed to slowly warm to room temperature and stir for an additional hour whereupon LCMS indicated reaction completion. The reaction was quenched with the addition of sat. NH4Cl. Volatiles were removed in vacuo, and the resulting residue was diluted with DCM. The layers were separated, and the organic layer was washed with water x 2, 1 M NaOH, brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the desired product as a white solid (23.6 g, 94% yield). Spectral data were in accordance with reported literature values.3

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 6185 - 6188
[2]Tetrahedron Letters,2019,vol. 60,p. 743 - 745
[3]Organic Letters,2013,vol. 15,p. 472 - 475

9
[ 52387-36-7 ]
[ 90319-52-1 ]
[ 618-41-7 ]
(4R)-3-[1-(phenylsulfonyl)-6-chlorohexyl]-4-phenyloxazolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With magnesium sulfate In dichloromethane at 20℃; for 36h;

Reference： [1]Marcantoni, Enrico; Mecozzi, Tiziana; Petrini, Marino [Journal of Organic Chemistry, 2002, vol. 67, # 9, p. 2989 - 2994]

10
[ 124-38-9 ]
[ 201300-96-1 ]
[ 90319-52-1 ]
[ 160695-26-1 ]
2-Methyl-3-oxo-3-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-propionic acid [ No CAS ]

Reference： [1]Organic Letters,2002,vol. 4,p. 2617 - 2620
[2]Organic Letters,2002,vol. 4,p. 2617 - 2620
[3]Journal of Organic Chemistry,2004,vol. 69,p. 487 - 494

11
[ 90319-52-1 ]
[ 111409-79-1 ]
[ 503590-28-1 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 1151 - 1154
[2]Journal of the American Chemical Society,2003,vol. 125,p. 2368 - 2369
[3]Journal of Organic Chemistry,2006,vol. 71,p. 4170 - 4177
[4]Organic Letters,2009,vol. 11,p. 4462 - 4465

12
[ 90319-52-1 ]
[ 932-87-6 ]
[ 425605-13-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; 1,10-Phenanthroline; copper(II) sulphate hydrate; In toluene; at 80℃; for 15h;Inert atmosphere;	To a solution of bromoethynylbenzene (1.4 g, 8.0 mmol) in 24 mL of anhydrous toluene in a reaction vial were added methyl phenylcarbamate (1.5 g, 9.6 mmol), K3PO4 (3.4 g, 16 mmol), copper sulfate-pentahydrate (400 mg, 16 mmol), and 1,10-phenanthroline (577 mg, 3.2 mmol). The reaction mixtures was capped under an argon atmosphere, and heated in an oil bath at 80 ºC for 15 h. The progress of the reaction was monitored using TLC analysis. Upon completion, the reaction mixture was allowed to cool to room temperature, and diluted with 15 mL of ethyl acetate. The mixture was filtered through a pad of celite, and the filtrate was concentrated in vacuo. The crude residue was purified by column chromatography with eluent of Hexane/ ethyl acetate = 19/1 to give 1.6 g of 1 in 80 percent yield as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.55 (dd, J = 1.2, 8.6 Hz, 2H), 7.45-7.40 (m, 4H), 7.33-7.28 (m, 4H), 3.92 (s, 3H). 13C NMR. (100 MHz, CDCl3) delta 154.9, 139.7, 131.5, 129.1, 128.4, 128.0, 127.2, 124.8, 123.0, 83.0, 70.3, 54.5.#10;
	With 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; potassium carbonate; In toluene; at 80℃;Inert atmosphere;	General procedure: Procedure 1: To a solution of alkyne (9.80 mmol, 1.0 equiv) in acetone (10 mL) was added NBS (10.78 mmol, 1.1 equiv) and AgNO3 (0.98 mmol, 0.1 equiv). The resulting solution was stirred under nitrogen at room temperature for 4 h. After removing excess acetone the reaction was quenched with water and extracted with petroleum ether three times, dried over MgSO4, and concentrated under reduced pressure. The residue was eluted through a short silica column (petroleum ether) to obtain the bromoalkyne. To a dried flask was added 2-oxazolidone (4.8 mmol, 1.2 equiv), CuSO4·5H2O (100 mg, 0.4 mmol, 0.1 equiv), 1,10-phenanthroline (144 mg, 0.8 mmol, 0.2 equiv) and K2CO3 (1.38 g, 10.0 mmol, 2.5 equiv), bromoalkyne (4.0 mmol, 1.0 equiv) and this mixture was subsequently treated with anhydrous toluene (10 mL). The flask was charged with nitrogen, and the solution was heated at 80 °C overnight. After completion, the crude reaction mixture was cooled to room temperature, filtered and concentrated in vacuo. Purification of the crude residue using silica gel flash column chromatography yielded the pure ynamides.

Reference： [1]Organic Letters,2004,vol. 6,p. 1151 - 1154
[2]Tetrahedron Letters,2006,vol. 47,p. 3139 - 3143
[3]Journal of Organic Chemistry,2006,vol. 71,p. 4170 - 4177
[4]Journal of the American Chemical Society,2003,vol. 125,p. 2368 - 2369
[5]European Journal of Organic Chemistry,2019,vol. 2019,p. 1166 - 1169
[6]Journal of Organic Chemistry,2009,vol. 74,p. 4630 - 4633
[7]Tetrahedron Letters,2013,vol. 54,p. 1309 - 1311
[8]Tetrahedron,2017,vol. 73,p. 2731 - 2739
[9]Journal of Organic Chemistry,2019,vol. 84,p. 914 - 923
[10]Organic and biomolecular chemistry,2020,vol. 18,p. 3374 - 3381

13
[ 140-10-3 ]
[ 90319-52-1 ]
[ 155835-37-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With trichlorophosphate at 70℃; for 2.5h;	Synthesis of compounds 1a-b; general procedure General procedure: A mixture of (4R or 4S)-4-phenyl-oxazolidin-2-one (6.5 g, 41.4 mmol),trans-cinnamic acid (6.8 g, 46 mmol), and phosphorus oxychloride(13 mL) was heated at 70 °C for 2.5 h. The process was monitored byTLC. The reaction mixture was slowly cooled to room temperatureand quenched by the addition of ice water (80 mL). Ice water (50 mL)was added again when the bubbles vanished, and the mixture wasstirred at 0 °C for 1 h. The precipitate was filtered off and this crudeproduct was purified by recrystallisation (ethyl acetate: hexane = 1 : 1)to give the pure product.
80%	Stage #1: (E)-3-phenylacrylic acid With oxalyl dichloride In dichloromethane at 20℃; for 4h; Inert atmosphere; Stage #2: (4R)-phenyl-2-oxazolidinone With triethylamine In dichloromethane at 0 - 20℃;	Step 1. (R)-3-Cinnamoyl-4-phenyloxazolidin-2-one To a solution of cinnamic acid (12.0 g, 81.0 mmol) in DCM (50 mL), cooled at 0 °C under a N2 atmosphere, oxalyl chloride (13.9 mL, 162 mmol) was added dropwise. The resulting solution was then stirred at r.t. for 4 h and finally it was concentrated to dryness to render cinnamoyl chloride (quant. yield assumed). To a stirred solution of (R)-4-phenyloxazolidin-2-one (13.2 g, 81.0 mmol) and TEA (16.9 mL, 121 mmol) in DCM (50 mL), cooled at 0 °C, a solution of the previously prepared cinnamoyl chloride (81.0 mmol) in DCM (8 mL) was added dropwise. The mixture was stirred at 0 °C for 1 h and then left to warm to r.t. overnight. NH4Cl sat. sol. was then added and it was extracted with DCM. The combined organic phases were dried over Na2SO4, filtered and concentrated to dryness. The resulting crude solid was slurried in hot EtOAc (5 volumes), then it was allowed to cool down to r.t. The solids were collected by filtration and dried under vacuum to give the title compound (19.12 g, 80% yield).
	Stage #1: (E)-3-phenylacrylic acid With pivaloyl chloride; triethylamine In tetrahydrofuran Stage #2: (4R)-phenyl-2-oxazolidinone With n-butyllithium at -78 - -20℃;

Reference： [1]Yang, Rui; Guo, Ya-Fei; Gao, Zhan-Yong; Zhao, Qian; Zhang, Qian-Yang; Lin, Jun [Journal of Chemical Research, 2015, vol. 39, # 2, p. 86 - 89]
[2]Current Patent Assignee: Corporacion Quimico Farmaceutica Esteve SA - EP3858438, 2021, A1 Location in patent: Paragraph 0160
[3]Xu, Jinyou; Wei, Lan; Mathvink, Robert; He, Jiafang; Park, You-Jung; He, Huaibing; Leiting, Barbara; Lyons, Kathryn A.; Marsilio, Frank; Patel, Reshma A.; Wu, Joseph K.; Thornberry, Nancy A.; Weber, Ann E. [Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 10, p. 2533 - 2536]

14
[ 18944-77-9 ]
[ 90319-52-1 ]
(R)-3-[(E)-3-(2-Fluoro-phenyl)-acryloyl]-4-phenyl-oxazolidin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2533 - 2536

15
[ 20595-30-6 ]
[ 90319-52-1 ]
(R)-3-[(E)-3-(3-Fluoro-phenyl)-acryloyl]-4-phenyl-oxazolidin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2533 - 2536

16
[ 943-89-5 ]
[ 90319-52-1 ]
[ 161274-69-7 ]

Yield	Reaction Conditions	Operation in experiment
98%		Oxalyl chloride (4.7 mL, 56.1 mmol) was added drop-wise to a mixture of commercially available (£)-3-(4-methoxyphenyl)acrylic acid (B12, 5.0 g, 28.1 mmol) in anhydrous dichloromethane (80 mL) at 0 °C under nitrogen, after which and anhydrous DMF (0.5 mL) was added. The mixture was slowly warmed to room temperature, stirring for a total of 3 h. (i?)-4-Phenyl-oxazolidin-2-one (4.6 g, 28.1 mmol) and DMAP (100 mg) were added, followed by triethylamine (5.3 mL, 36.5 mmol), and the mixture was heated to 50 °C to stir for 12 h. The mixture was cooled to room temperature, the solvents were removed under reduced pressure and the residue was triturated with diethyl ether to provide (R,E)-3-[3-(4- methoxyphenyl)acryloyl]-4-phenyloxazolidin-2-one [(i?)B13] as a light yellow solid (8.9 g, 98percent): LCMS (M+H) 324.

Reference： [1]Patent: WO2018/152293,2018,A1 .Location in patent: Page/Page column 61
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2533 - 2536

17
[ 140134-65-2 ]
[ 90319-52-1 ]
(R)-3-[(E)-3-(4-Methylsulfanyl-phenyl)-acryloyl]-4-phenyl-oxazolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (E)-3-<4-(methylthio)phenyl>propenoic acid With pivaloyl chloride; triethylamine In tetrahydrofuran Stage #2: (4R)-phenyl-2-oxazolidinone With n-butyllithium at -78 - -20℃;

Reference： [1]Xu, Jinyou; Wei, Lan; Mathvink, Robert; He, Jiafang; Park, You-Jung; He, Huaibing; Leiting, Barbara; Lyons, Kathryn A.; Marsilio, Frank; Patel, Reshma A.; Wu, Joseph K.; Thornberry, Nancy A.; Weber, Ann E. [Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 10, p. 2533 - 2536]

18
[ 90319-52-1 ]
[ 84315-23-1 ]
(4R)-3-[(2E)-3-(3,5-difluorophenyl)prop-2-enoyl]-4-phenyl-1,3-oxazolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61.5%		Preparation of (i?,E)-3-(3-(3,5-difluorophenyl)acryloyl)-4-phenyloxazolidin-2-one: To a solution of (E)-3-(3,5-difluorophenyl)acrylic acid (10.0 g, 54.3 mmol) in Et20 (150 mL) at 0 °C was added DIEA (9.48 mL, 54.3 mmol) followed by pivaloyl chloride (6.69 mL, 54.3 mmol). The mixture was stirred at 0 °C for 1 hour and cooled to - 78 °C. Meanwhile (R)-4- phenyloxazolidin-2-one (8.86 g, 54.3 mmol) in THF (200 mL) was cooled to -78 °C and butyllithium (21.7 mL, 2.5 M, 54.3 mmol) was added slowly. The mixture was stirred for 20 minutes at -78 °C and transferred by cannula to the solution of mixed anhydride. The combined mixture was stirred at -78 °C for 15 min, allowed to warm to 0 °C and stirred for an additional 30 minutes. The reaction mixture was quenched with saturated NH4C1 (25 mL), diluted with EtOAc (600 mL), washed with water, NaHC03, and brine, dried over MgSC^, and concentrated in vacuo. The crude material was purified by silica column chromatography, eluting with 10-20percent Ethyl acetate/Hexanes to afford the product (11.0 g, 61.5percent yield).
61.5%		Step A: Preparation of (R,E)-3-(3-(3,5-difluorophenyl)acryloyl)-4- phenyloxazolidin-2-one: To a solution of (E)-3-(3,5-difluorophenyl)acrylic acid (10.0 g, 54.3 mmol) in Et20 (150 mL) at 0 °C was added DIEA (9.48 mL, 54.3 mmol) followed by pivaloyl chloride (6.69 mL, 54.3 mmol). The mixture was stirred at 0 °C for 1 hour and cooled to - 78 °C. Meanwhile (R)-4-phenyloxazolidin-2-one (8.86 g, 54.3 mmol) in THF (200 mL) was cooled to -78 °C and butyllithium (21.7 mE, 2.5 M, 54.3 mmol) was added slowly. The mixture was stirred for 20 minutes at -78 °C and transferred by cannula to the solution of mixed anhydride. The combined mixture was stirred at -78 °C for 15 mm, allowed to warm to 0 °C and stirred for an additional 30 minutes. The reaction mixture was quenched with saturated NH4CI (25 mL), diluted with EtOAc (600 mL), washed with water, NaHCO3, and brine, dried over MgSO4, and concentrated in vacuo. The crude material was purified by silica column chromatography, eluting with 10-20percent Ethyl acetate/Hexanes to afford the product (11.0 g, 61.5percent yield).

Reference： [1]Patent: WO2012/158413,2012,A2 .Location in patent: Page/Page column 83
[2]Patent: WO2014/78323,2014,A1 .Location in patent: Paragraph 00527
[3]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2533 - 2536

19
[ 90319-52-1 ]
[ 112897-97-9 ]
(R)-3-[(E)-3-(3,4-Difluoro-phenyl)-acryloyl]-4-phenyl-oxazolidin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2533 - 2536

20
[ 90319-52-1 ]
[ 174603-37-3 ]
(R)-3-[(E)-3-(2-Chloro-4-fluoro-phenyl)-acryloyl]-4-phenyl-oxazolidin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2533 - 2536

21
[ 90319-52-1 ]
[ 155814-22-5 ]
(R)-3-[(E)-3-(3-Chloro-4-fluoro-phenyl)-acryloyl]-4-phenyl-oxazolidin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2533 - 2536

22
[ 39887-30-4 ]
[ 90319-52-1 ]
4-(2-oxo-4-phenyloxazolidin-3-yl)-N-(propyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; potassium carbonate; rac-diaminocyclohexane In 1,4-dioxane Heating;

Reference： [1]Ghosh, Arun; Sieser, Janice E.; Caron, Stephane; Couturier, Michel; Dupont-Gaudet, Kristina; Girardin, Melina [Journal of Organic Chemistry, 2006, vol. 71, # 3, p. 1258 - 1261]

23
[ 90319-52-1 ]
[ 41658-03-1 ]
((R)-2-Oxo-4-phenyl-oxazolidin-3-yl)-propynoic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 4170 - 4177

24
[ 86217-38-1 ]
[ 123-62-6 ]
[ 90319-52-1 ]
[ 99395-88-7 ]
[ 160695-26-1 ]
[ 184363-66-4 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 6536 - 6537

25
[ 41233-93-6 ]
[ 90319-52-1 ]
[ 451-81-0 ]
[ 216754-32-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium chloride; In water; toluene;	A solution of 46.0 g of (R)-4-phenyl-2-oxazolidinone in 300 g (338 mL) of peroxide-free tetrahydrofuran is cooled to -5 to 0 C. (bath temperature -10 to -5 C.) over a period of 15 minutes. 145.2 g (166.8 mL) of 25% w/w potassium t-amylate/toluene solution is added over a period of 25 minutes while maintaining an internal temperature below 0 C. The reaction mixture is warmed to 20+-5 C. within 1 hour and stirred at this temperature for 2.5-3 hours. The mixture is cooled to -15 to -5 C. over a period of 30 minutes, and crude 2-fluorobenzenacetyl chloride (obtained above) is added over a period of 45 minutes while maintaining an internal temperature below -5 C. (bath temperature -15 to -10 C.). After the addition is completed, the mixture is warmed to 20+-5 C. over a period of 1 hour, and diluted with 100 mL of toluene. This is added to 500 mL of saturated citric acid monosodium salt solution (100 g in 450 g of water) and the mixture is stirred for 5 minutes. The organic layer is separated, and washed with 1 L of sodium chloride solution (200 g in 800 g of water) in two equal portions of 500 mL each. The solution is concentrated to dryness under reduced pressure (66-76 mm Hg, bath temperature 65-70 C.) to obtain 3-[2-(2-fluorophenyl)-1-oxoethyl]-4(R)-phenyl-2-oxazolidinone as a semi-solid.

Reference： [1]Patent: US6174888,2001,B1

26
[ 54447-68-6 ]
[ 90319-52-1 ]
[ 215812-05-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With n-butyllithium; thionyl chloride; sodium hydrogencarbonate;N-methyl-acetamide; In tetrahydrofuran; hexane; dichloromethane; water;	Production Example 1 (4R) -3- (4-Azidobutanoyl)4-phenyloxazolidin-2-one A catalytic amount of dimethylformamide was added to a solution of 4-azidobutyric acid (10.3 g, 80.0 mM) in 100 ml of methylene chloride and, thereafter, thionyl chloride (8.7 ml, 119.5 mM) was added dropwise thereto under ice-cooling. After stirring the reaction mixture at room temperature for one hour, it was evaporated to give a crude acid chloride. A 1.6M solution of n-butyl lithium in hexane (40.2 ml, 64.3 mM) was added dropwise into a solution of (4R)-4-phenyl-2-oxazolidinone (manufactured by Aldrich; 10 g, 61.3 mM) in tetrahydrofuran (80 ml) at -78° C. and the mixture was stirred at the same temperature for 30 minutes. A solution of the previously synthesised acid chloride in tetrahydrofuran (100 ml) was slowly added dropwise into the reaction mixture and the mixture was further stirred for 30 minutes. The reaction was ceased by adding dropwise a saturated aqueous solution of sodium bicarbonate into the reaction mixture followed by warming up to room temperature. The mixture was poured into water followed by extracting with ethyl acetate and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water and brine in this order and dried over anhydrous magnesium sulfate. The solvent was removed and the residue was subjected to a silica gel column chromatography (hexane/ethyl acetate=5/1) to give the title compound (17 g, 99percent). 1H-NMR(CD Cl3) delta:1.84(2H,quint,J=7 Hz), 2.88(2H,t,J=7 Hz), 3.25 (2H,t,J=7 Hz),4.24(1H,dd,J=4.9 Hz), 4.65(1H,t,J=7 Hz), 5.36(1H,dd,J=4.9 Hz), 7.22-7.35(5H,m).

Reference： [1]Patent: US6218550,2001,B1

27
[ 214492-02-1 ]
[ 7782-24-3 ]
[ 90319-52-1 ]

Yield	Reaction Conditions	Operation in experiment
90%; 93%		Lithium hydroxide monohydrate (71 mg, 1.69 mmol) was slowly added to a stirred solution of oxazolidin-2-one (S,R)-syn-41 (0.25 g, 0.84 mmol) and hydrogen peroxide (0.47 mL, 3.53 M in H2O, 1.69 mmol) in THF/water (1:1; 5 mL). The reaction mixture was stirred at room temperature for 12 h. The reaction was quenched with water (10 mL) and extracted with dichloromethane (3 .x. 10 mL). The combined organic layers were dried (over MgSO4) and evaporated under reduced pressure to give the recovered 4-phenyloxazolidin-2-one (R)-8 (127 mg, 93percent) as a white solid; RF [ethyl acetate/ethanol (9:1)] 0.71; mp 130-133 °C; inlMMLBox (c 1.0, CHCl3); numax (CHCl3)/cm-1 3262 (NH) and 1736 (CO); deltaH (400 MHz; CDCl3) 7.41-7.31 (5H, m, 5 .x. CH; Ph), 5.69 (1H, s, NH), 4.93 (1H, dd, J 8.6 and 6.9, PhCHN), 4.72 (1H, t, J 8.6, CHAHBO) and 4.17 (1H, dd, J 8.6 and 6.9, CHAHBO); deltaC (100 MHz; CDCl3) 159.4 (CO), 139.3 (i-C; Ph), 129.2,2 128.91 and 126.02 (5 .x. CH; Ph), 72.5 (CH2O) and 56.3 (PhCHN) (Found inlMMLBox, 181.0970; C9H13N2O2 requires 181.0972). The aqueous phase was acidified using HCl (3 M HCl) until the pH = 3, and extracted with diethyl ether (3 .x. 10 mL). The combined organic phases were dried (over MgSO4) and evaporated under reduced pressure to give 2-phenylpropanoic acid (S)-53 (113 mg, 90percent) as a colourless oil; RF [light petroleum spirit (bp 40-60 °C)/diethyl ether (1:9)] 0.5; inlMMLBox (c 8.2, CHCl3); numax (CHCl3)/cm-1 1706 (CO); deltaH (400 MHz; CDCl3) 7.45-6.98 (5H, m, 5 .x. CH; Ph), 3.75 (1H, q, J 7.2, PhCHCH3) and 1.50 (3H, d, J 7.2, PhCHCH3); deltaC (100 MHz; CDCl3) 180.4 (CO), 139.7 (i-C; Ph), 128.7,2 127.62 and 127.41 (5 .x. CH; Ph), 45.3 (PhCHCH3) and 18.1 (PhCHCH3) (Found inlMMLBox, 151.0753; C9H11NO2 requires 151.0759).

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 439 - 463
[2]Tetrahedron Asymmetry,2008,vol. 19,p. 1536 - 1548

28
[ 102089-75-8 ]
[ 289051-61-2 ]
[ 90319-52-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 40% 2: 6%	Stage #1: (-)-(1R)-1-[(1',1'-dimethylethoxycarbonyl)amino]-2-(methylsulfonyl)oxy-1-phenylethane With potassium thioacetate In tetrahydrofuran; methanol at 20℃; for 24h; Stage #2: With ammonia In tetrahydrofuran; methanol at 20℃; for 0.166667h; Saturated solution;

Reference： [1]Location in patent: experimental part Weber, Immo; Heinemann, Frank W.; Bauer, Walter; Zenneck, Ulrich [Zeitschrift fur Naturforschung, B: Chemical Sciences, 2009, vol. 64, # 1, p. 123 - 140]

29
[ 102089-75-8 ]
[ 108-98-5 ]
[ 90319-52-1 ]
[ 140372-83-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: (-)-(1R)-1-[(1',1'-dimethylethoxycarbonyl)amino]-2-(methylsulfonyl)oxy-1-phenylethane; thiophenol With potassium <i>tert</i>-butylate In methanol at 20℃; for 18h; Stage #2: With hydrogenchloride In methanol; water

30
[ 15851-92-0 ]
[ 90319-52-1 ]
(4R)-3-((2E)-3-(3-methoxyphenyl)acryloyl)-4-phenyl oxazolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%		(R,E)-3- (3- (3-methoxy) phenyl) acryloyl)-4- phenyl oxazolidin-2-one The 4R-phenyl-2-oxazolidinone (5.6g, 34.4mmol) was placed in a three-necked flask, after it was purged with nitrogen, tetrahydrofuran was added and it was cooled to -78°C, then n-butyl lithium (1.6M, 22ml, 35.4mmol) was added dropwise, and the reaction was carried out for 30 minutes. After a solution of m-methoxy cinnamoyl chloride (10.3g, 37.8mmol) in tetrahydrofuran was added dropwise, the reaction was continued for 30 minutes, then it was slowly raised to 0°C, the reaction was continued for 2 hours and quenched with saturated ammonium chloride solution. The mixture was concentrated to remove tetrahydrofuran and extracted with ethyl acetate 3 times, then the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated, and recrystallized with petroleum ether and ethyl acetate to give a white solid 10.3g, yield: 92percent. 1HNMR(300MHz, CDCl3): delta 8.0(1H, d, J=15.3), 7.8(1H, d, J=15.7), 7.2-7.4(6H, m), 7.1-7.2(2H, m), 7.0(1H, d, J=8.6), 5.6(1H, dd, J=4.0,9.0), 4.8(1H, t, J=8.8,17.5), 4.3(1H, dd, J=4.0, 8.8), 3.8 (3H, s). ESI-MS: 346.3 (M+Na).
92%		Example 11 (R,E)-3-(3-(3-methoxy)phenyl)acryloyl)-4-phenyl oxazolidin-2-one The 4R-phenyl-2-oxazolidinone (5.6 g, 34.4 mmol) was placed in a three-necked flask, after it was purged with nitrogen, tetrahydrofuran was added and it was cooled to -78° C., then n-butyl lithium (1.6M, 22 ml, 35.4 mmol) was added dropwise, and the reaction was carried out for 30 minutes. After a solution of m-methoxy cinnamoyl chloride (10.3 g, 37.8 mmol) in tetrahydrofuran was added dropwise, the reaction was continued for 30 minutes, then it was slowly raised to 0° C., the reaction was continued for 2 hours and quenched with saturated ammonium chloride solution. The mixture was concentrated to remove tetrahydrofuran and extracted with ethyl acetate 3 times, then the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated, and recrystallized with petroleum ether and ethyl acetate to give a white solid 10.3 g, yield: 92percent. 1HNMR (300 MHz, CDCl3): delta 8.0 (1H, d, J=15.3), 7.8 (1H, d, J=15.7), 7.2-7.4 (6H, m), 7.1-7.2 (2H, m), 7.0 (1H, d, J=8.6), 5.6 (1H, dd, J=4.0, 9.0), 4.8 (1H, t, J=8.8, 17.5), 4.3 (1H, dd, J=4.0, 8.8), 3.8 (3H, s). ESI-MS: 346.3 (M+Na).

Reference： [1]Patent: EP2671878,2013,A1 .Location in patent: Paragraph 0084; 0085
[2]Patent: US2014/46074,2014,A1 .Location in patent: Paragraph 0171-0172
[3]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 2388 - 2399

31
[ 7436-90-0 ]
[ 90319-52-1 ]
[ 425605-13-6 ]

Yield	Reaction Conditions	Operation in experiment
82%	With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine In 1,4-dioxane at 60℃; for 24h; Inert atmosphere; regioselective reaction;
82%	With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine Heating;

Reference： [1]Coste, Alexis; Karthikeyan, Ganesan; Couty, Francois; Evano, Gwilherm [Angewandte Chemie - International Edition, 2009, vol. 48, p. 4381 - 4385][Angew. Chem., Int. Ed., 2009, vol. 121, p. 4445 - 4449]
[2]Jouvin, Kevin; Coste, Alexis; Bayle, Alexandre; Legrand, Frederic; Karthikeyan, Ganesan; Tadiparthi, Krishnaji; Evano, Gwilherm [Organometallics, 2012, vol. 31, # 22, p. 7933 - 7947]

32
Z-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-butenoic acid [ No CAS ]
[ 90319-52-1 ]
(4R)-3-[(2Z)-[4-[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-oxo-2-buten-1-yl]-4-phenyl-2-oxazolidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%		(4R)-3-[(2Z)-[4-[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1-oxo-2-buten-1-yl]-4-phenyl-2-oxazolidinone (7) To a solution of acid 6 (6.0 g, 28.2 mmol) in THF (40 mL) at -78 C., was added triethylamine (4.00 mL, 28.2 mmol) followed by trimethylacetyl chloride (3.46 mL, 28.2 mmol) drop-wise. The mixture was warmed to 0 C. over 20 minutes, then the anhydride mixture was cooled to -78 C. Separately, to a solution of (R)-(+)-phenyl-2-oxazolidione (Aldrich) (4.60 g, 28.2 mmol) in THF (40 mL) at -78 C. was carefully added n-BuLi (2.50 M in THF, 11.3 mL, 28.2 mmol) and the mixture was stirred (30 minutes) then transferred to the anhydride solution at -78 C. The final reaction mixture was warmed to room temperature and stirred (over night). The mixture was diluted with EtOAc (200 mL), washed (H2O and brine), dried (Na2SO4), and purified by silica gel column chromatography (hexanes:EtOAc) to yield 7 as a colorless oil (10.2 g, 100% yield). 1H NMR (400 MHz, CDCl3) delta 7.36-7.20 (m, 5H), 7.10 (dt, J=11.6, 2.6 Hz, 1H), 6.50 (dt, J=12.0, 4.6 Hz, 1H), 5.44 (dd, J=8.8, 4.0 Hz, 1H), 4.68-4.59 (m, 3H), 4.22 (dd, J=8.8, 4.0 Hz, 1H), 0.85 (s, 9H), 0.00 (s, 6H). 13C NMR (100 MHz, CDCl3) delta 169.3, 160.6, 158.8, 144.3, 134.5, 134.0, 131.0, 122.0, 75.2, 67.9, 62.8, 31.1, 23.4, 0.00. ESI (+VE) m/z: 384.1 (M+Na)+. HR-ESI cacld for C19H28NO4Si (M+Na)+: 362.1782, Found: 362.1789.

Reference： [1]Tetrahedron,2009,vol. 65,p. 9673 - 9679
[2]Patent: US10266565,2019,B2 .Location in patent: Page/Page column 199; 200

33
C₁₇H₂₉NO₅ [ No CAS ]
[ 90319-52-1 ]
[ 1159845-42-7 ]

Yield	Reaction Conditions	Operation in experiment
70.7 g	With n-butyllithium In tetrahydrofuran; hexane at -60 - 20℃; for 72h; Cooling;

Reference： [1]Location in patent: experimental part Monovich, Lauren G.; Tommasi, Ruben A.; Fujimoto, Roger A.; Blancuzzi, Vincent; Clark, Kirk; Cornell, Wendy D.; Doti, Robert; Doughty, John; Fang, James; Farley, David; Fitt, John; Ganu, Vishwas; Goldberg, Ronald; Goldstein, Robert; Lavoie, Stacey; Kulathila, Raviraj; Macchia, William; Parker, David T.; Melton, Richard; O'Byrne, Elizabeth; Pastor, Gary; Pellas, Theodore; Quadros, Elizabeth; Reel, Noela; Roland, Dennis M.; Sakane, Yumi; Singh, Hem; Skiles, Jerry; Somers, Joseph; Toscano, Karen; Wigg, Andrew; Zhou, Siyuan; Zhu, Lijuan; Shieh, Wen-Chung; Xue, Song; McQuire, Leslie W. [Journal of Medicinal Chemistry, 2009, vol. 52, # 11, p. 3523 - 3538]

34
[ 90319-52-1 ]
[ 84773-28-4 ]

Yield	Reaction Conditions	Operation in experiment
		Synthesis 31; (f?)-2-(Methylamino)-2-phenylethanol (ABD81 Oe)A solution of LiAIH4 (1.0 M in THF, 184 ml_, 0.184 mol) was added to a solution of (F?)-(-)-phenyloxazolidin-2-one (15.0 g, 0.092 mol) in THF and then heated at reflux for 1.5 hours. The mixture was then cooled in an ice bath and quenched by portion-wise addition of sodium sulphate decahydrate, until bubbling ceased. The mixture was filtered through Celite and partitioned between EtOAc (200 mL) and water (100 ml_). The layers were separated and the aqueous phase was extracted with EtOAc (3 x 100 mL). After drying over MgSO4 the solvents were evaporated, giving the title compound as a yellow oil, which crystallised on standing to give an off white solid (10.3 g, 75%).

Reference： [1]Patent: WO2010/32010,2010,A1 .Location in patent: Page/Page column 92

35
(4R)-3-((2S)-2-phenylbutanoyl)-4-phenyl-oxazolidin-2-one [ No CAS ]
[ 4286-15-1 ]
[ 90319-52-1 ]

Yield	Reaction Conditions	Operation in experiment
91%; 82%		In the same way as the 2-phenylpropanoic acid (S)-53, oxazolidin-2-one (S,R)-syn-42 (0.2 g, 0.64 mmol), lithium hydroxide monohydrate (53 mg, 1.28 mmol) and hydrogen peroxide (0.36 mL, 3.53 M in H2O, 1.28 mmol) in THF/water (1:1; 3 mL) gave, the recovered 4-phenyl oxazolidin-2-one (R)-8 (95 mg, 82percent) as a white solid; and 2-phenylbutanoic acid (S)-54 (95 mg, 91percent) as a colourless oil; inlMMLBox (c 4.0, CHCl3); numax (CHCl3)/cm-1 3295 (OH) and 1719 (CO); deltaH (400 MHz; CDCl3) 7.30-7.20 (5H, m, 5 .x. CH; Ph), 3.43 (1H, t, J 7.7; PhCHCO), 2.16-2.03 (1H, ddq, J 7.5, 7.5 and 7.4, CHAHBCH3), 1.85-1.79 (1H, ddq, J 7.5, 7.5 and 7.4, CHAHBCH3) and 0.90 (3H, t, J 7.4, CH2CH3); deltaC (100 MHz; CDCl3) 181.0 (CO), 138.6 (i-C; Ph), 128.8,2 128.22 and 127.61 (5 .x. CH; Ph), 53.6 (PhCHCO), 26.5 (CH2CH3) and 12.2 (CH2CH3) (Found M+, 164.0832; C10H12O2 requires 164.0832).

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 439 - 463
[2]Tetrahedron Letters,2010,vol. 51,p. 5892 - 5895

36
(4R,2'S)-3-[2'-(4-methylphenyl)propionyl]-4-phenyl-oxazolidin-2-one [ No CAS ]
[ 90319-52-1 ]
[ 124709-72-4 ]