[ CAS No. 264600-97-7 ]

Name: 264600-97-7|tert-Butyl isoxazol-3-ylcarbamate|95%
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SKU: A392898
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 264600-97-7 ]

CAS No. :	264600-97-7	MDL No. :	MFCD11100913
Formula :	C₈H₁₂N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	184.19 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 264600-97-7 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.5
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	46.75
TPSA :	64.36 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) :	-6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.89
Log Po/w (XLOGP3) :	1.27
Log Po/w (WLOGP) :	1.83
Log Po/w (MLOGP) :	0.65
Log Po/w (SILICOS-IT) :	0.52
Consensus Log Po/w :	1.23

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.8
Solubility :	2.9 mg/ml ; 0.0158 mol/l
Class :	Very soluble
Log S (Ali) :	-2.22
Solubility :	1.11 mg/ml ; 0.00602 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.19
Solubility :	1.19 mg/ml ; 0.00646 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.7

Safety of [ 264600-97-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P270-P301+P312-P330	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 264600-97-7 ]

* 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 [ 264600-97-7 ]

[ 264600-97-7 ] Synthesis Path-Downstream 1~33

1
[ 264600-97-7 ]
[ 543683-28-9 ]
5(S)-5-[N-(t-butoxycarbonyl)-N-(1,2-isoxadiazolyl-3-yl)]-3-[4-(1-cyanocyclopropan-1-yl)-3-fluorophenyl]aminomethyloxazolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		16 Example 16; 5(S)-5-[N-(t-Butoxycarbonyl)-N-(1,2-isoxadiazolyl-3-yl)]-3-[4-(1-cyanocyclopropan-1-yl)-3-fluorophenyl]aminomethyloxazolidin-2-one The title compound 5(S)-5-[N-(t-butoxycarbonyl)-N-(1,2-isoxadiazolyl-3-yl)]-3-[4-(1-cyanocyclopropan-1-yl)-3-fluorophenyl]amino-methyloxazolidin-2-one (364 mg) was prepared from 5(R)-3-[4-(1-cyanocyclopropan-1-yl)-3-fluorophenyl]-5-hydroxymethyloxazolidin-2-one (250 mg) and 3-N-(t-butoxycarbonyl)aminoisoxazole (250 mg) in the same manner as described for EXAMPLE 15. MS (EI+) m/z: 442 (M+). [0280] HRMS (EI+) for C22H23FN4O5 (M+): calcd, 442.1652; found, 442.1650.

Reference： [1]Current Patent Assignee: MERCK & CO INC - US2003/225107, 2003, A1 Location in patent: Page 21

2
[ 1750-42-1 ]
[ 24424-99-5 ]
[ 264600-97-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	With dmap In pyridine for 18h;	8 To a stirred solution of 3-aminoisoxazole (5.00 g, 59.5 mmol) and 4-(dimethylamino) pyridine (500 mg) in pyridine (100 ml) was added portionwise di-tert-butyl dicarbonate (25.97 g, 119 mmol) and stirred for 18 hours. The solvent was removed by rotary evaporation giving an oil that was dissolved in methanol (100 ml) and treated with NaOH solution (2.5M, 24 ml, 60 mmol), stirred for 2 hours, acidified with citric acid solution (10%w/v, 80 ml), and added to water (500 ml), giving the title compound as a tan coloured solid after filtration and drying (8.89 g, 81%). NMR (300Mz, DMSO-d6), δ/ppm: 1.46 (s, 9H), 6.72 (d, 1H), 8.71 (d, 1H), 10.35 (s, broad, 1H). MS: ES+(M+H)=129 (loss of butylene).
80%	With pyridine; dmap In dichloromethane at 5 - 10℃; for 24h; Large scale;	3 Step three, in a 25L reactor, add 12kg of dichloromethane, 1.3kg of compound D,66g DMAP, 1.28kg pyridine, stirred and cooled to 10 ° C,3.2 kg of di-tert-butyl dicarbonate was slowly added dropwise to the reaction solution, and the reaction temperature was controlled at 5-10 ° C for 24 hours.After the reaction was completed, the reactant was washed once with 24 kg of a 1% hydrochloric acid solution and stirred for 30 minutes.Allow to stand, separate the liquid, and use 14 kg of water for the organic phase.14 kg of a mass concentration of 5% NaHCO 3 aqueous solution and 14 kg of saturated saline were washed once, respectively.The organic phase was separated and concentrated under reduced pressure until no liquid flowed out. After adding 16 kg of ethyl acetate, the mixture was dissolved and 0.3 kg of activated carbon was added.After heating at 50-60 ° C for 30 min, after cooling to room temperature, add 1 kg of anhydrous sodium sulfate and dry for 30 min.Filtration, the filtrate was concentrated to a small volume under reduced pressure, then 10 kg of petroleum ether was added and stirred at room temperature for 2 h.Filtration gave Compound E as a white solid, 2.28 kg, yield 80%.
69%	With dmap In dichloromethane at 20℃; for 18h;	5 Intermediate 5. Preparation of isoxazol-3-ylcarbamic acid, tert-butyl ester A mixture of 28.5 g (0.338 mol) of 3-aminoisoxazole in 950 mL of dichloromethane was prepared, and 2.8 g (0.023 mol) of 4-dimethylaminopyridine, and 147.7 g (0.677 mol) of di-tert-butyl dicarbonate were added. The mixture was stirred at room temperature for 18 h, and the solvent was distilled off under reduced pressure. The residue was dissolved in 570 mL of methanol, and 180 mL of a 2 N sodium hydroxide aqueous solution were added. The mixture was stirred for 2 h, and then 450 mL of an 10% citric acid aqueous solution were added to adjust pH between 4 and 5. Stirring was continued for some minutes and the solution was poured over 2.8 L of water. The solid was filtered and dissolved in 500 mL of dichloromethane. The solution was dried over anhydrous sodium sulfate, and filtered, and the solvent was distilled off under reduced pressure. The residual solid was broken up with hexane. 42. 9 g (yield = 69%) of a yellow solid were obtained. IR (KBr): 3257, 1732 cm-1. Mass spectrum (m/e): 184 (M+).

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US2003/207899, 2003, A1 Location in patent: Page/Page column 42
[2]Current Patent Assignee: SHANGHAI LINKCHEM TECH - CN109369553, 2019, A Location in patent: Paragraph 0030; 0034
[3]Current Patent Assignee: LABORATORIOS SALVAT S.A. - EP1437349, 2004, A1 Location in patent: Page 29

3
N-[5(S)-3-[4-[2-[(1α,5α,6β)-6-cyano-3-oxabicyclo[3.1.0]hexan-6-yl]-pyridin-5-yl]-3-fluorophenyl]]-5-hydroxymethyloxazolidin-2-one [ No CAS ]
[ 264600-97-7 ]
5(R)-5-[N-(t-butoxycarbonyl)-N-(isoxazol-3-yl)]aminomethyl-3-[4-[2-[(1α,5α,6β)-6-cyano-3-oxabicyclo[3.1.0]hexan-6-yl]pyridin-5-yl]-3-fluorophenyl]oxazolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tributylphosphine; diamide In toluene at 50℃; for 2h;	67 EXAMPLE 67 5 (R)-5- [N- (T-BUTOXYCARBONYL)-N- (ISOXAZOL-3-YL)] AMINOMETHYL-3- [4- [2- [ (LA, 5A, 6P)-6-CYANO-3- oxabicyclo [3.1. 0] hexan-6-yl] PYRIDIN-5-YL]-3-FLUOROPHENYL] oxazolidin-2-one. To a suspension OFN- [5 (S)-3- [4- [2- [ (LA, 5A, 6P)-6-CYANO-3-OXABICYCLO [3.1. 0] HEXAN-6-YL]-PYRIDIN-5- YL]-3-FLUOROPHENYL]-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE (300 mg), 3-N- (T- butoxycarbonyl) AMINOISOXAZOLE (168 mg), and tetramethylazodicarboxamide (196 mg) in toluene (7.5 mL) was added tributylphosphine (230 mg), and the mixture was stirred at 50 °C for 2 hours. Flash chromatography (silica, hexane: ethyl acetate = 1 : 1) of the mixture gave 5 (R)-5- [N- (T- BUTOXYCARBONYL)-N- (ISOXAZOI-3-YL)] AMINOMETHYI-3- [4- [2- [ (LA, 5A, 6 (3)-6-CYANO-3- NXAHICVCLOR3. I. OLHEXAN-6-YL] PYRIDIN-5-YL]-3-FLUOROPHENYL] oxazolidin-2-one (392 mg). MS (FAB+) M/Z : 562 (MH+). HRMS (FAB+) for C29H29FN506 (MH+) : calcd, 562.2102 ; found, 562.2123.

Reference： [1]Current Patent Assignee: KYORIN HOLDINGS, INC. - WO2005/5398, 2005, A2 Location in patent: Page 73-74

4
[ 827015-17-8 ]
[ 264600-97-7 ]
5(R)-3-[4-[(1α,5α,6β)-(3-t-butoxycarbonyl-6-cyano-3-azabicyclo[3.1.0]hexan-6-yl)]phenyl]-5-[N-(t-butoxycarbonyl)-N-(isoxazol-3-yl)]aminomethyloxazolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tributylphosphine; diamide In benzene at 20℃; for 1.5h;	15 To a suspension OF 5 (R)-3- [4- [ (LA, 5OC, 6 (3)- (3-T-BUTOXYCARBONYL-6-CYANO-3- azabicyclo [3.1. 0] hexan-6-yl) ] phenyl] -5-hydroxymethyloxazolidin-2-one (10.0 mg), 3-N- (T- butoxycarbonyl) AMINOISOXAZOLE (9.2 mg), and tetramethylazodicarboxamide (8. 6 mg) in benzene (0.25 mL) was added tributylphosphine (12. 5 UL), and the mixture was stirred at room temperature for 90 minutes. After dilution of the mixture with ethyl acetate, the insoluble materials were filtered off, and the filtrate was concentrated in vacuo. Flash chromatography (silica, hexane: ethyl acetate = 3: 5) of the mixture gave 5 (R)-3- [4- [ (la, 5A, 6ß)-(3-t-butoxycarbonyl-6-cyano-3-azabicyclo [3.1. 0] hexan-6-yl) ] phenyl]-5- [N- (t- BUTOXYCARBONYL)-N- (ISOXAZOL-3-YL)] AMINOMETHYLOXAZOLIDIN-2-ONE (14.1 mg). MS (FAB+) m/z : 566 (MH+). HRMS (FAB+) for C29H36N5O7 (MH+) : calcd, 566.2615 ; found, 566.2609.

Reference： [1]Current Patent Assignee: KYORIN HOLDINGS, INC.; MERCK & CO INC - WO2005/5399, 2005, A1 Location in patent: Page/Page column 28-29

5
[ 264600-97-7 ]
[ 252337-07-8 ]
[ 264600-53-5 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-N-(t-butoxycarbonyl)amino-1,2-isoxazole; (5R)-3-(4-(2-methylimidazol-1-yl)-3-fluorophenyl)-5-hydroxymethyloxazolidin-2-one With triphenylphosphine In N,N-dimethyl-formamide at 0℃; Stage #2: With di-isopropyl azodicarboxylate In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	9 3-(2-Methylimidazol-1-yl-3-fluorophenyl)-5(R)-hydroxymethyloxazolidin-2-one (582 mg, 2 mM), 3-(t-butoxycarbonylamino)isoxazole (552 mg, 3 mM), and triphenylphosphine (786 mg, 3 mM) were dissolved by stirring in dry N,N-dimethylformamide (10 ml) under nitrogen in an ice-bath. Diisopropylazodicarboxylate (606 mg, 3 mM) was added dropwise, and the mixture stirred 2 hours, allowing the temperature to rise to ambient. The mixture was diluted with ethyl acetate (100 ml), washed with water (100 ml), 2% aqueous sodium bicarbonate (100 ml), and brine (100 ml). After drying (magnesium sulfate), the residue was purified by chromatography on a 20 g silica Mega Bond Elut column, eluting with a gradient increasing in polarity from 0 to 5% methanol in dichloromethane. Relevant fractions were combined to give the desired product (590 mg). [0444] NMR(DMSO-d6) δ: 1.47 (s, 9H); 2.14 (s, 3H); 3.91 (dd, 1H); 4.00 (dd, 1H); 4.25 (dd, 1H); 4.29 (t, 1H); 5.02 (m, 1H); 6.85 (d, 1H); 6.92 (d, 1H); 7.20 (d, 1H); 7.47 (dd, 1H); 7.55 (t, 1H); 7.71 (dd, 1H); 8.79 (d, 1H). MS (ESP): 458 (MH+) for C22H24FN5O5

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US2003/207899, 2003, A1 Location in patent: Page/Page column 29

6
[ 264600-97-7 ]
[ 196299-06-6 ]
[ 264600-52-4 ]

Yield	Reaction Conditions	Operation in experiment
	With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In tetrahydrofuran at 0 - 20℃; for 18h;	8 5(S)-Isoxazol-3-ylaminomethyl-3-(4-(4-Hydroxymethylimidazol-1-yl)-3-fluorophenylhoxazolidin-2-one 3-(4-(4-t-Butyldimethylsilyloxymethylimidazol-1-yl)-3-fluorophenyl)-5(R)-hydroxy-methyloxazolidin-2-one (842 mg, 2 mM, see WO 97-31917) and 3-(t-butoxycarbonylamino)isoxazole (405 mg, 2.2 mM) were suspended by stirring in dry tetrahydrofuran (15 ml) under nitrogen in an ice-bath. Tributylphosphine (444 mg, 2.2 mM) followed by 1,1'-(azo-dicarbonyl)dipiperidine (555 mg, 2.2 mM) dissolved in tetrahydrofuran (10 ml) were added. The mixture was then stirred 18 hours, allowing the temperature to rise to ambient, then filtered, and the filter cake washed with tetrahydrofuran. The combined filtrates were evaporated and the residue purified by chromatography on a 10 g reversed phase C18 column, eluding with a gradient from 10 to 50% acetonitrile in water containing 0.1% trifluoroacetic acid. Relevant fractions were combined, evaporated, and the residue rechromatographed on a 10 g silica Mega Bond Elut column, eluding with a gradient increasing in polarity from 0 to 20% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (104 mg). MS (ESP): 474 (MH+) for C22H24FN5O6NMR (DMSO-d6): δ: 1.49 (s, 9H); 3.92 (m, 1H); 4.00 (m, 1H); 4.27 (m, 2H); 4.50 (s, 2H); 5.05 (m, 1H); 6.85 (d, 1H); 7.53 (t, 1H); 7.66 (d, 1H); 7.76 (overlapping m, 2H); 8.67 (d, 1H); 8.80 (d, 1H). (H of OH missing-exchanged).

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US2003/207899, 2003, A1 Location in patent: Page/Page column 28

7
[ 264600-97-7 ]
5(R)-hydroxymethyl-3-(4-(1-benzyl-1,2,5,6-tetrahydropyrid-4yl)-3,5-difluorophenyl)oxazolidin-2-one [ No CAS ]
5(R)-((N-isoxazol-3-yl-N-tertbutoxycarbonyl)aminomethyl)-3-(3,5-difluoro-4-(1-benzyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl)oxazolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In tetrahydrofuran at 0 - 20℃; for 4.5h;	33.9 To a stirred solution of 5(R)-hydroxymethyl-3-(3,5-difluoro-4-(1-benzyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl)oxazolidin-2-one (Reference Example 9D; 6.01 g, 15 mmol), 3-(tert-butyloxycarbonylamino)-isoxazole (3.04 g, 16.5 mmol; Reference Example 8) and tri-n-butyl phosphine (4.55 g, 22.5 mmol, 5.55 ml) in dry THF (250 ml), under N2, cooled to 0° C., was added portionwise 1,1'-(azodicarbonyl)-di-piperidine (5.68 g, 22.5 mmol). The reaction was stirred at 0° C. for 30 mins, allowed to come to ambient temperature and stirred for a further 4 hours, with the formation of a white precipitate. The mixture was filtered, concentrated by rotary evaporation to an oil which was purified by MPLC (Merck 9385 silica, 50%EtOAc/Hexane), concentrating the pure fractions to give the title compound as a white brittle foam (7.74 g, 91%). [0683] NMR (300Mz, DMSO-d6), δ/ppm: δ 2.33 (m, 2H), 3.41 (t, 2H), 3.53 (m, 1H), 3.66 (m, 1H), 3.79 (dd, 1H), 4.10 (m, 5H), 4.57 (m, 1H), 4.89 (m, 1H), 5.83 (m, 1H), 5.98 (d, 1H), 6.50 (t, 1H), 7.33 (d, 2H), 8.38 (d, 1H). MS: ES+(M+H)=567.

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US2003/207899, 2003, A1 Location in patent: Page/Page column 43

8
[ 154590-63-3 ]
[ 264600-97-7 ]
[ 882185-11-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In N,N-dimethyl-formamide at 80℃; for 17h;	6.a Sodium hydride (0.23 g) and tert-butyl isoxazol-3-ylcarbamate (0.88 g) were added to a solution of tert-butyl 4-[2-fluoro-4-((5R)-5-[(methylsulfonyl)oxy]methyl}-2- oxo-1,3-oxazolidin-3-yl)phenyl]piperazine-1-carboxylate(l g) (which can be prepared according to Example l(h) given in WO93/23384, at page 13) in dry dimethylformamide (10 mL) and the reaction mixture was stirred at 80 °C for about 17 hours. The reaction mixture was extracted with ethyl acetate and the organic layer was washed with water, dried over sodium sulfate and concentrated. The crude product thus obtained was purified by column chromatography using 2 % methanol in dichloromethane as eluent to yield the title compound (1 g).

Reference： [1]Current Patent Assignee: SUN PHARMACEUTICAL INDUSTRIES LIMITED - WO2006/35283, 2006, A1 Location in patent: Page/Page column 46; 47

9
[ 154590-63-3 ]
[ 264600-97-7 ]
C₂₇H₃₆FN₅O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In N,N-dimethyl-formamide at 80℃; for 2h;
	With sodium hydride In N,N-dimethyl-formamide at 0 - 80℃; for 1h;	1.a To a solution of tert-butyl 4-[2-fluoro-4-((5i?)-5-[(methylsulfonyl)oxy]methyl}-2- oxo-l,3-oxazolidin-3-yl)phenyl]piperazine-l-carboxylate (prepared axcording to the procedure given in WO 93/23384) (1.5g) in dimethylformamide(20ml) was added ter- butyl-isoxzol-3-yl-carbamate(0.65g) in presence of sodium hydride at O0C and the reaction mixture was heated at 80° C for I hour. The reaction mixture was cooled, quenched with cold water and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to get the title compound(l .52g)

Reference： [1]Location in patent: scheme or table Das, Biswajit; Rajarao; Rudra, Sonali; Yadav, Ajay; Ray, Abhijit; Pandya, Manisha; Rattan, Ashok; Mehta, Anita [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 22, p. 6424 - 6428]
[2]Current Patent Assignee: SUN PHARMACEUTICAL INDUSTRIES LIMITED - WO2006/43121, 2006, A1 Location in patent: Page/Page column 21

10
[ 264600-97-7 ]
[ 250372-89-5 ]
tert-butyl 4-[4-((5R)-5-[(tert-butoxycarbonyl)(isoxazol-3-yl)amino]methyl}-2-oxo-1,3-oxazolidin-3-yl)-2-fluorophenoxy]piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In N,N-dimethyl-formamide at 80℃; for 17h;	7.a Sodium hydride (0.15 g) and tert-butyl isoxazol-3-ylcarbamate (0.87 g) were added to a solution of tert-butyl 4-[2-fluoro-4-((5R)-5-[(methylsulfonyl)oxy]methyl}-2- oxo-1,3-oxazolidin-3-yl)phenoxy]piperidine-1-carboxylate (1.5 g) (which can be prepared according to Example 6, after the first step in the conversion of the compound 6 to 7, in Biorg. Med. Chem. Lett., 11 (2001), 1829-1832, at page 1830) in dry dirnethylformamide (10 mL). The reaction mixture was stirred at 80 °C for about 17 hours. The reaction mixture was extracted with ethyl acetate and the organic layer was washed with water, dried over sodium sulfate and concentrated. The crude product thus obtained was purified by column chromatography using 2 % methanol in dichloromethane as eluent to yield the title compound (2 g).

Reference： [1]Current Patent Assignee: SUN PHARMACEUTICAL INDUSTRIES LIMITED - WO2006/35283, 2006, A1 Location in patent: Page/Page column 48

Yield	Reaction Conditions	Operation in experiment
		1 3-(t-Butoxycarbonylamino)isoxazole 3-(t-Butoxycarbonylamino)isoxazole 3-Aminoisoxazole (10 g, 0.12 M) and 4-dimethylaminopyridine (500 mg, 4.1 mM) were dissolved in pyridine (200 ml), and treated in portions with di-t-butyl dicarbonate (51.94 g, 0.24 M). The mixture was stirred at ambient temperature for 18 hours, then evaporated to dryness. The residue was dissolved in methanol (200 ml) and treated with sodium hydroxide solution (2N, 60 ml), then stirred for 2 hours. After acidification with aqueous citric acid (10%, 160 ml), the mixture was added to water (750 ml), and the desired product (15.9 g) collected by filtration. NMR (DMSO-d6) δ: 1.46 (s, 9H); 6.69 (d, 1H); 8.68 (d, 1H); 10.27 (s, 1H).

12
[ 264600-97-7 ]
[ 106-95-6 ]
N-Allyl-3-(t-butoxycarbonylamino)isoxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,2-dimethoxyethane	1 N-Allyl-3-(t-Butoxycarbonylamino)isoxazole N-Allyl-3-(t-Butoxycarbonylamino)isoxazole 3-(t-Butoxycarbonylamino)isoxazole (12 g, 65.2 mM) was dissolved in dimethoxyethane (150 ml) and cooled to 0°C under nitrogen. To the stirred solution was added sodium hydride (60% in oil, 2.87 g, 71.7 mM), and the mixture stirred 20 minutes. Allyl bromide (8.7 g, 71.7 mM) was added dropwise, and the mixture stirred at ambient temperature for 18 hours, then diluted with water (300 ml), and extracted into diethyl ether (3 x 100 ml). The extracts were washed with brine (100 ml), dried (magnesium sulfate), and chromatographed on silica (50 g) eluding with dichloromethane. Relevant fractions were combined to give the desired product as an oil (14.68 g). MS (ESP) : 225 (MH+) for C11H16N2O3 NMR (CDCl3) δ: 1.54 (s, 9H); 4.47 (dm, 2H); 5.18 (m, 2H); 5.92 (m, 1H); 6.87 (d, 1H); 8.22 (d, 1H).

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - EP1242416, 2005, B1

13
[ 264600-97-7 ]
[ 252340-85-5 ]
[ 264600-54-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-N-(t-butoxycarbonyl)amino-1,2-isoxazole With sodium hydride In N,N-dimethyl-formamide for 0.166667h; Stage #2: {(5R)-3-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl methanesulfonate In N,N-dimethyl-formamide at 35℃; for 1.5h;	10 3-(4(4-methylimidazol-1-yl)-3-fluorophenyl)-5(R)-(N-(t-butoxycarbonyl)isoxazol-3-yl-aminomethyl)oxazolidin-2-one Sodium hydride (50% in oil, 72 mg, 1.5 mM) was stirred in N,-dimethylformamide (3 ml) under nitrogen, and 3-(t-butoxycarbonylamino)isoxazole (276 mg, 1.5 mM), dissolved in N,N-dimethylformamide (4 ml) added. After stirring for 10 minutes, 3-(4-methylimidazol-1-yl-3-fluorophenyl)-5(R)-methanesulfonyloxymethyloxazolidin-2-one (369 mg, 1 mM) was added, the mixture warmed to 35° for 1.5 hours. The mixture was diluted with aqueous sodium bicarbonate (30 ml), extracted with ethyl acetate (320 ml), and the extract washed with water (220 ml), and brine (20 ml). After drying (magnesium sulfate), the residue was purified by chromatography on a 20 g silica Mega Bond Elut column, eluding with a gradient increasing in polarity from 0 to 50% acetone in dichloromethane. Relevant fractions were combined to give the desired product (228 mg). NMR (DMSO-d6) δ: 1.49 (s, 9H); 2.17 (s, 3H); 3.90 (dd, 1H); 4.01 (m, 1H); 4.25 (t, 1H); 4.28 (dd, 1H); 5.04 (m, 1H); 6.86 (d, 1H); 7.22 (d, 1H); 7.46 (dd, 1H); 7.63 (t, 1H); 7.72 (dd, 1H); 7.86 (d, 1H); 8.81 (d, 1H). MS (ESP): 458 (MH+) for C22H24FN5O5

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US2003/207899, 2003, A1 Location in patent: Page/Page column 30

14
[ 264600-97-7 ]
[ 1112968-97-4 ]
[ 1112969-00-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: 3-N-(t-butoxycarbonyl)amino-1,2-isoxazole With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 5 - 20℃; Stage #2: C₁₆H₁₅F₃N₂O₆S In N,N-dimethyl-formamide at 40℃;	3.B Method B. A solution of tent-butyl isoxazol-3-ylcarbamate (13.2 g, 67.2 mmol) in DMF (30 mL) was added to a mixture of ButOK (16.8 g, 64 mmol) in DMF (60 mL) at 5° C. The mixture was then warmed up to 20° C. and stirred for 1 h. The resulting solution was added to a mixture of Intermediate 6 (13.4 g, 32 mmol) in DMF (60 mL) and heated at 40° C. for 3 h. Additional reagent pre-made as above from tert-butyl isoxazol-3-ylcarbamate and ButOK (6.4 mmol, 0.2 eq) was added, and the mixture was stirred for 2 h. The latter process was repeated again until Intermediate 6 was consumed. The reaction mixture was cooled to r.t. and poured into water (300 mL) and extracted with EtOAc (3×200 mL). The combined organic layers were washed with 10% aq. NaCl (3×300 mL), brine (300 mL), and dried over MgSO4. The solution was filtered and the filtrate was condensed under vacuum. The residue was recrystallized from EtOH (20 mL) and water (18.5 mL). The collected solid was suspended in methyl tert-butyl ether (MTBE, 50 mL) and stirred for 4 h. The product was collected as a pale yellow solid (12 g, 75%). 1H NMR (400 MHz, CDCl3): 8.28 (s, 1H); 7.44 (m, 1H); 7.09 (d, J=7.6 Hz, 1H); 7.00 (s, 1H); 5.32 (d, J=7.6 Hz, 1H); 5.15 (m, 1H); 4.44 (m, 1H); 4.20 (m, 2H); 3.94 (m, 3H); 2.70 (t, J=7.4 Hz, 2H); 1.45 (s, 9H). MS (m/z): 509 [M+H].
	Stage #1: 3-N-(t-butoxycarbonyl)amino-1,2-isoxazole With sodium hydride In N,N-dimethyl-formamide at 35℃; for 0.25h; Stage #2: C₁₆H₁₅F₃N₂O₆S In N,N-dimethyl-formamide at 50℃; for 1.5h;	5.A A solution of tert-butyl isoxazol-3-ylcarbamate (187 mg, 100 mmol) in DMF (1 mL) was added dropwise with stirring to a suspension of NaH (60% in mineral oil, 48 mg, 1.20 mmol) in DMF (2 mL). The mixture was stirred under N2 for 15 min. at 35° C. The Intermediate 22 (357 mg, 0.85 mmol) in DMF (1 mL) was added, and the mixture was stirred at 50° C. for 1.5 h. The reaction mixture was taken into EtOAc (30 mL), washed with 10% aq. NH4Cl (2×15 mL), brine, and dried (Na2SO4). Solvent was removed under vacuum and the crude material was purified by column chromatography (2% MeOH/DCM) to afford the product as a light yellow solid.
	Stage #1: 3-N-(t-butoxycarbonyl)amino-1,2-isoxazole With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: C₁₆H₁₅F₃N₂O₆S In N,N-dimethyl-formamide at 35℃; for 2h;	5.B A solution of tert-butyl isoxazol-3-ylcarbamate (694 mg, 3.8 mmol) in DMF (3 mL) was added dropwise with stirring to ButOK (439 mg, 3.8 mmol) in DMF (3 mL) at 0° C. The mixture was warmed up to r.t. and stirred for 30 min. The Intermediate 22 (1.34 g, 3.2 mmol) in DMF (6 mL) mL) was added, and the mixture was stirred at 35° C. for 2 h. The reaction was quenched with saturated aq. NH4Cl solution (10 mL), and isolation performed just as described above for Method A to afford the product as a light yellow solid. 1H NMR (400 MHz): 8.28 (s, 1H), 7.44 (m, 1H), 7.09 (d, J=7.6 Hz, 1H), 7.00 (s, 1H, 5.32 (d, J=7.6 Hz, 1H), 5.15 (m, 1H), 4.44 (m, 1H), 4.20 (m, 2H, 3.94 (m, 3H), 2.70 (t, J=7.4 Hz, 2H), 1.45 (s, 9H). MS (m/z): 509 [M+H].

Reference： [1]Current Patent Assignee: SHANGHAI MICURX PHARMACEUTICAL - US2010/204477, 2010, A1 Location in patent: Page/Page column 17-18
[2]Current Patent Assignee: SHANGHAI MICURX PHARMACEUTICAL - US2009/48305, 2009, A1 Location in patent: Page/Page column 19-20
[3]Current Patent Assignee: SHANGHAI MICURX PHARMACEUTICAL - US2009/48305, 2009, A1 Location in patent: Page/Page column 20

15
[ 264600-97-7 ]
[ 1112969-09-1 ]
[ 1112969-13-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-N-(t-butoxycarbonyl)amino-1,2-isoxazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 35℃; Inert atmosphere; Stage #2: C₁₆H₁₆F₂N₂O₆S In N,N-dimethyl-formamide; mineral oil at 50℃; for 1.5h;	12 Example 12; Compound of Structure Scheme for Compound of Example 12: Intermediate 22. A solution of tert-butyl isoxazol-3-ylcarbamate (86 mg, 0.47 mmol) in DMF (1 mL) was added dropwise with stirring to a suspension of NaH (60% in mineral oil, 19 mg, 0.47 mmol) in DMF (1 mL). The mixture was stirred under N2 for 15 min. at 35° C. The Intermediate 18 (0.43 mmol) in DMF (1.00 mL) was added, and the mixture was stirred at 50° C. for 1.5 h. The reaction mixture was taken into EtOAc (30 mL), washed with 10% aq. NH4Cl (2×15 mL), brine, and dried (Na2SO4). Solvent was removed under vacuum and the crude product was purified by column chromatography (2% MeOH/DCM) to afford the product as a yellow solid.
	Stage #1: 3-N-(t-butoxycarbonyl)amino-1,2-isoxazole With sodium hydride In N,N-dimethyl-formamide at 35℃; for 0.25h; Stage #2: C₁₆H₁₆F₂N₂O₆S In N,N-dimethyl-formamide at 50℃; for 1.5h;	14 A solution of tert-butyl isoxazol-3-ylcarbamate (86 mg, 0.47 mmol) in DMF (1 mL) was added dropwise with stirring to a suspension of NaH (60% in mineral oil, 19 mg, 0.47 mmol) in DMF (1 mL). The mixture was stirred under N2 for 15 min. at 35° C. The Intermediate 34 (0.43 mmol) in DMF (1.00 mL) was added, and the mixture was stirred at 50° C. for 1.5 h. The reaction mixture was taken into EtOAc (30 mL), washed with 10% aq. NH4Cl (2×15 mL), brine, and dried (Na2SO4). Solvent was removed under vacuum and the crude product was purified by column chromatography (2% MeOH/DCM) to afford the product as a yellow solid.

Reference： [1]Current Patent Assignee: SHANGHAI MICURX PHARMACEUTICAL - US2010/204477, 2010, A1 Location in patent: Page/Page column 23
[2]Current Patent Assignee: SHANGHAI MICURX PHARMACEUTICAL - US2009/48305, 2009, A1 Location in patent: Page/Page column 25

16
[ 264600-97-7 ]
[ 1112969-39-7 ]
[ 1112969-40-0 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-N-(t-butoxycarbonyl)amino-1,2-isoxazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 35℃; Inert atmosphere; Stage #2: C₁₇H₁₈F₂N₄O₅S In N,N-dimethyl-formamide; mineral oil at 50℃; for 1.5h;	24 Intermediate 47. A solution of tent-butyl isoxazol-3-ylcarbamate (45.0 mg, 0.24 mmol) in DMF (1 mL) was added dropwise with stirring to a suspension of NaH (60% in mineral oil, 9.8 mg, 0.24 mmol) in DMF (2 mL). The mixture was stirred under Ar for 15 min. at 35° C., and then cooled down to r.t. The Intermediate 46 (95.1 mg, 0.22 mmol) in DMF (1 mL) was added, and the mixture was stirred at 50° C. for 1.5 h. The reaction mixture was taken into EtOAc (30 mL), washed with 10% aq. NH4Cl (2×15 mL), brine, and dried (Na2SO4). Solvent was removed under vacuum and the crude product was purified by preparative TLC (2.4% MeOH/DCM) to afford the product as a white solid. MS (m/z): 517 [M+H].
	Stage #1: 3-N-(t-butoxycarbonyl)amino-1,2-isoxazole With sodium hydride In N,N-dimethyl-formamide at 35℃; for 0.25h; Stage #2: C₁₇H₁₈F₂N₄O₅S In N,N-dimethyl-formamide at 20 - 50℃; for 1.5h;	24 A solution of tert-butyl isoxazol-3-ylcarbamate (45.0 mg, 0.24 mmol) in DMF (1 mL) was added dropwise with stirring to a suspension of NaH (60% in mineral oil, 9.8 mg, 0.24 mmol) in DMF (2 mL). The mixture was stirred under Ar for 15 min. at 35° C., and then cooled down to r.t. The Intermediate 61 (95.1 mg, 0.22 mmol) in DMF (1 mL) was added, and the mixture was stirred at 50° C. for 1.5 h. The reaction mixture was taken into EtOAc (30 mL), washed with 10% aq. NH4Cl (2×15 mL), brine, and dried (Na2SO4). Solvent was removed under vacuum and the crude product was purified by preparative TLC (2.4% MeOH/DCM) to afford the product as a white solid. MS (m/z): 517 [M+H].

Reference： [1]Current Patent Assignee: SHANGHAI MICURX PHARMACEUTICAL - US2010/204477, 2010, A1 Location in patent: Page/Page column 33
[2]Current Patent Assignee: SHANGHAI MICURX PHARMACEUTICAL - US2009/48305, 2009, A1 Location in patent: Page/Page column 33

17
[ 264600-97-7 ]
[ 831202-98-3 ]
5(R)-3-[4-[2-[(1α,5α,6β)-3-tert-butoxycarbonyl-6-cyano-3-azabicyclo[3.1.0]hexan-6-yl]pyridin-5-yl]-3-fluorophenyl]5-[N-(tert-butoxycarbonyl)-N-(isoxazol-3-yl)]aminomethyloxazolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With tributylphosphine; diamide In toluene at 50℃; for 6h;

Reference： [1]Komine, Takashi; Kojima, Akihiko; Asahina, Yoshikazu; Saito, Tatsuhiro; Takano, Hisashi; Shibue, Taku; Fukuda, Yasumichi [Journal of Medicinal Chemistry, 2008, vol. 51, # 20, p. 6558 - 6562]

18
[ 501939-82-8 ]
[ 264600-97-7 ]
[ 501939-83-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-N-(t-butoxycarbonyl)amino-1,2-isoxazole With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; Stage #2: (5R)-methanesulfonic acid 3-(3-fluoro-4-iodophenyl)-2-oxo-oxazolidin-5-ylmethyl ester In DMF (N,N-dimethyl-formamide) at 75℃; for 2h;	O-tert-Butyl N-(5R)-3-{3-fluoro-4-iodophenyl}-1,3-oxazolidin-2-on-5-yl)methyl N-isoxazol- 3-ylcarbamate A solution of N-isoxazol-3-yl-carbamic acid tert-butyl ester (1.66 g, 9.04 mmol) in N, N-DIMETHYLFORMAMIDE (10 mL) was added dropwise at ambient temperature to a stirred suspension of sodium hydride (60% in oil, 9.04 mol) in dry N, N-DIMETHYLFORMAMIDE (10 ML) under an atmosphere of nitrogen. The mixture was treated slowly with a solution of methane sulfonic acid (5R)-3- (3-FLUORO-4-IODO-PHENYL) oxazolidin-2-one-5-ylmethyl ester (2.5 g, 6.02 mmol) in N, N-DIMETHYLFORMAMIDE (10 mL) and the reaction mixture was heated to 75°C for 2 hours. After cooling, the mixture was diluted with aqueous sodium bicarbonate (5%, 300 mL), and extracted with ethyl acetate (3 x 100 mL). The organic phase was washed with water (100 mL) and brine (100 mL), dried (magnesium sulfate), evaporated and crude product purified by chromatography on a 50 g silica Mega Bond ELUT (G) column, eluting with dichloromethane. Relevant fractions were combined to give the title compound (1.73 g). MS (ESP) : 504 (MH+) for C18H19FIN3O5 NMR (DMSO-D6) B : 1.47 (s, 9H); 3.84 (dd, 1H) ; 3.96 (dd, 1H); 4.19 (t, 1H); 4.99 (dd, 1H); 4.99 (m, 1H) ; 6.83 (d, 1H); 7.19 (dd, 1H) ; 7.53 (dd, 1H) ; 7.82 (dd, 1H); 8.79 (d, 1H).

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2004/56816, 2004, A1 Location in patent: Page 55

19
[ 264600-97-7 ]
3-(3,4-difluorophenyl)isoxazol-5-methyl methylsulfonate [ No CAS ]
[ 492992-50-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: 3-N-(t-butoxycarbonyl)amino-1,2-isoxazole With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 5℃; for 0.75h; Stage #2: 3-(3,4-difluorophenyl)isoxazol-5-methyl methylsulfonate at 40℃; for 16h;	6 Intermediate 6. Preparation of isoxazol-3-yl[3-(3,4-difluorophenyl)isoxazol-5-ylmethyl]carbamic acid, tert-butyl ester A solution of 34.4 g (0.186 mol) of isoxazol-3-ylcarbamic acid, tert-butyl ester (Intermediate 5) in 750 mL of N,N-dimethylformamide was prepared and cooled down with an ice bath to a temperature comprised between 0 and 5C. 7.5 g (0.187 mol) of a 60% sodium hydride suspension in paraffin were added under inert atmosphere, and the mixture was stirred at low temperature for 45 minutes. Then, 34.1 g (0.12 mol) of 3-(3,4-difluoro-phenyl)isoxazol-5-methyl methylsulfonate (Intermediate 4) were added. The mixture was stirred at 40C for 16 h, and then allowed to cool down at room temperature. The reaction crude was poured over 5 L of a 5% sodium bicarbonate aqueous solution and the final solution was extracted three times with 1.5 L of ethyl acetate. The organic layer was washed five times with 1 L of saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and filtered, and the solvent was distilled off under reduced pressure. The residual solid was broken up with hexane. 39 g (yield = 88%) of a yellow solid was obtained. IR (KBr): 1717 cm-1. Mass spectrum (m/e): 391 (M+).

Reference： [1]Current Patent Assignee: LABORATORIOS SALVAT S.A. - EP1437349, 2004, A1 Location in patent: Page 29

20
[ 264600-97-7 ]
[ 1219708-15-2 ]
[ 1219708-23-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In N,N-dimethyl-formamide; mineral oil at 80℃;	12 Boc-3-aminoisoxazole (1.22g, 6.6 mmol) was dissolved in DMF (40 mL) and stirred for 30 minutes after adding 50% NaH (0.32 g, 6.6 mmol). After slowly adding Compound VI (3.6 g, 6.6 mmol) dissolved in DMF (10 mL) dropwise, the solution was stirred at 800C for 4 hours. The solution was cooled to room temperature, diluted with ethyl acetate, washed twice with water, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to obtain Compound XIV (4.16 g, 6.4 mmol).

Reference： [1]Current Patent Assignee: LEGOCHEM BIOSCIENCES INC. - WO2010/36000, 2010, A2 Location in patent: Page/Page column 32

21
[ 264600-97-7 ]
[ 1364337-78-9 ]
[ 1364337-88-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-N-(t-butoxycarbonyl)amino-1,2-isoxazole With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 0℃; for 2h; Stage #2: C₁₉H₁₈FN₃O₇S In N,N-dimethyl-formamide at 0 - 20℃;	3 Intermediate 6. A mixture of tert-butyl isoxazol-3-ylcarbamate (107 mg, 0.58 mmol (prepared as described in the publication US2009/48305) and t-BuOK (71 mg, 0.63 mmol) in DMF (1 mL) was stirred at 0° C. for 2 h. A solution of Intermediate 5 (130 mg, 0.29 mmol) in DMF (1 mL) was added dropwise. The reaction mixture was warmed up to r.t. and stirred o.n. Water (20 mL) was added and the mixture was extracted with EtOAc, washed with brine and dried (Na2SO4). After evaporation, the solid was washed with MeOH, and the desired product was obtained as a white solid.

Reference： [1]Current Patent Assignee: MICURX PHARMACEUTICALS - US2012/65170, 2012, A1 Location in patent: Page/Page column 16

22
[ 264600-97-7 ]
[ 952150-17-3 ]
[ 1443005-66-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With tributylphosphine In tetrahydrofuran at 20℃; for 21h;	4.1.42. 5(R)-(Isoxazol-3-yl-N-(tert-butoxycarbonyl)aminomethyl)-3-(3-fluoro-4-(1-(benzyloxycarbonyl)-2-(tert-butoxycarbonyl) [1,2,5]triazepan-5-yl)phenyl)oxazolidin-2-one (17a) General procedure: To a solution of compound4a(383.1mg, 0.703mmol) in THF (3mL) was added tri-n-butylphosphine (590.1mg, 2.917mmol), ADDP (709.6mg, 2.812mmol) and isoxazol-3-yl-carbamic acidtert-butyl ester (454.3mg, 2.466mmol). The mixture was stirred for 21h at ambient temperature. Evaporation of the solvent followed by silica gel (20g) column chromatography of the residue usingn-hexane/AcOEt (80:20 to 40:60) as the eluent afforded17a(465.1mg, 93%). Amorphous solid;1H NMR (CDCl3)δ=1.33-1.60 (18H, m,t-C4H9×2), 3.17-3.60 (6H, m, -CH2-), 3.75 (1H, br dd,J=6, 9Hz, oxazolidinone-H4), 3.97-4.28 (3H, m, -CH2-), 4.11 (1H, dd,J=4.9, 14.6Hz, -CHH-NBoc-isozazole), 4.36 (1H, dd,J=7.7, 14.6Hz, -CHH-NBoc-isoxazole), 5.00-5.10 (1H, m, oxazolidinone-H5), 5.05-5.29 (2H, m, Ar-CH2O), 6.88 (1H, t,J=9.1Hz, Ar-H5), 6.91 (1H, br s, isoxazole-H), 7.01-7.11 (1H, m, Ar-H6), 7.28-7.44 (6H, m, Ar-H), and 8.25 (1H, d,J=1.9Hz, isoxazole-H); EI-LRMSm/z: 610 (M+-Boc).

Reference： [1]Suzuki, Hideyuki; Utsunomiya, Iwao; Shudo, Koichi; Fukuhara, Norio; Iwaki, Tsutomu; Yasukata, Tatsuro [European Journal of Medicinal Chemistry, 2013, vol. 63, p. 811 - 825]

23
[ 264600-97-7 ]
[ 952150-39-9 ]
[ 1443005-67-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With tributylphosphine In tetrahydrofuran at 20℃; for 21h;	General procedure: To a solution of compound4a(383.1mg, 0.703mmol) in THF (3mL) was added tri-n-butylphosphine (590.1mg, 2.917mmol), ADDP (709.6mg, 2.812mmol) and isoxazol-3-yl-carbamic acidtert-butyl ester (454.3mg, 2.466mmol). The mixture was stirred for 21h at ambient temperature. Evaporation of the solvent followed by silica gel (20g) column chromatography of the residue usingn-hexane/AcOEt (80:20 to 40:60) as the eluent afforded17a(465.1mg, 93%).

Reference： [1]Suzuki, Hideyuki; Utsunomiya, Iwao; Shudo, Koichi; Fukuhara, Norio; Iwaki, Tsutomu; Yasukata, Tatsuro [European Journal of Medicinal Chemistry, 2013, vol. 63, p. 811 - 825]

24
[ 264600-97-7 ]
[ 952151-43-8 ]
[ 1443005-68-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	With tributylphosphine In tetrahydrofuran at 20℃; for 21h;	General procedure: To a solution of compound4a(383.1mg, 0.703mmol) in THF (3mL) was added tri-n-butylphosphine (590.1mg, 2.917mmol), ADDP (709.6mg, 2.812mmol) and isoxazol-3-yl-carbamic acidtert-butyl ester (454.3mg, 2.466mmol). The mixture was stirred for 21h at ambient temperature. Evaporation of the solvent followed by silica gel (20g) column chromatography of the residue usingn-hexane/AcOEt (80:20 to 40:60) as the eluent afforded17a(465.1mg, 93%).

Reference： [1]Suzuki, Hideyuki; Utsunomiya, Iwao; Shudo, Koichi; Fukuhara, Norio; Iwaki, Tsutomu; Yasukata, Tatsuro [European Journal of Medicinal Chemistry, 2013, vol. 63, p. 811 - 825]

25
[ 264600-97-7 ]
[ 856676-99-8 ]
[ 1401342-90-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	With sodium hydride In N,N-dimethyl-formamide at 0 - 75℃; for 2.5h;	31 Preparation of Compound B-III 2.5 g (6.87 mmol) of Compound XXX and 1.26 g (6.87 mmol) of Boc-aminoisoxazole were dissolved in 7 mL of dimethylformamide, 0.33 g (7.56 mmol) of NaH was added thereto at 0°C, and the resulting solution was stirred at 75°C for 2.5 hours. The reaction mixture was extracted using ethylacetate and distilled water to obtain an organic layer. The organic layer was dehydrated using anhydrous sodium sulfate, followed by concentration under reduced pressure and column chromatography, to obtain 2.61 g (5.72 mmol) of Compound B-III as a white solid (yield: 83%). [0173] 1H NMR (600MHz, CDCl3) δ 8.26 (d, J = 1.8 Hz, 1H), 7.53 (m, 2H), 7.14 (dd, J = 9.0 Hz, J = 3.0 Hz, 1H), 6.01 (br, 1 H), 5.92 (m, 1H), 4.37 (dd, J = 7.8 Hz, 1H), 4.12 (m, 2H), 3.81 (dd, J = 8.4 Hz, J = 4Hz, 1H), 1.56 (s, 9H)
83%	With sodium hydride In N,N-dimethyl-formamide at 0 - 75℃; for 2.5h;	31 Preparation of Compound B-III Preparation of Compound B-III 2.5 g (6.87 mmol) of Compound XXX and 1.26 g (6.87 mmol) of Boc-aminoisoxazole were dissolved in 7 mL of dimethylformamide, 0.33 g (7.56 mmol) of NaH was added thereto at 0° C., and the resulting solution was stirred at 75° C. for 2.5 hours. The reaction mixture was extracted using ethylacetate and distilled water to obtain an organic layer. The organic layer was dehydrated using anhydrous sodium sulfate, followed by concentration under reduced pressure and column chromatography, to obtain 2.61 g (5.72 mmol) of Compound B-III as a white solid (yield: 83%). [0185] 1H NMR (600 MHz, CDCl3) δ 8.26 (d, J=1.8 Hz, 1H), 7.53 (m, 2H), 7.14 (dd, J=9.0 Hz, J=3.0 Hz, 1H), 6.01 (br, 1H), 5.92 (m, 1H), 4.37 (dd, J=7.8 Hz, 1H), 4.12 (m, 2H), 3.81 (dd, J=8.4 Hz, J=4 Hz, 1H), 1.56 (s, 9H)

Reference： [1]Current Patent Assignee: LEGOCHEM BIOSCIENCES INC. - EP2692727, 2014, A2 Location in patent: Paragraph 0172-0173
[2]Current Patent Assignee: LEGOCHEM BIOSCIENCES INC. - US2014/179691, 2014, A1 Location in patent: Paragraph 0183-0185

26
[ 264600-97-7 ]
(R)-3-(3-fluoro-4-(2-oxa-6-azaspiro[3.3]heptan-6-yl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one [ No CAS ]
C₂₃H₂₇FN₄O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With tributylphosphine; (E)-N₁,N₁,N₂-trimethyldiazene-1,2-dicarboxamide In toluene at 0 - 60℃; Inert atmosphere;	12.5 Step 5: Preparation of (9): (E)-N,,N,,N2-trimethyldiazene- 1 ,2-dicarboxamide (443 mg, 2.6 mmol) was added to a suspension of (8) (523 mg, 1.7 mmol), tert-butyl isoxazol-3-ylcarbamate (380 mg, 2.1 mmol) and tributylphosphine (521 mg, 2.6 mmol) in toluene (30 mL) at 0 °C under a nitrogen gas atmosphere and then the reaction mixture was stirred at 60 °C for overnight, monitored by TLC. The mixture was concentrated under reduced pressure, and the crude material was purified by silica gel column chromatography (EA: PE = 10: 1) to afford (9) (298 mg, 37%) as a white solid.LC-MS (ESI) m/z = 475 [M+H].

Reference： [1]Current Patent Assignee: TB ALLIANCE INC - WO2017/15106, 2017, A1 Location in patent: Page/Page column 143; 145

27
[ 264600-97-7 ]
(R)-3-(3,5-difluoro-4-(2-oxa-6-azaspiro[3.3]heptan-6-yl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one [ No CAS ]
C₂₃H₂₆F₂N₄O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With tributylphosphine; (E)-N₁,N₁,N₂-trimethyldiazene-1,2-dicarboxamide In toluene at 0 - 60℃; Inert atmosphere;	12.7 Step 7: Preparation of (9): (E)-N1,N1,N2-trimethyldiazene-1,2-dicarboxamide (443 mg, 2.6 mmol) was added to a suspension of (8) (560 mg, 1.7 mmol), tert-butyl isoxazol-3-ylcarbamate (380 mg, 2.1 mmol) and tributylphosphine (521 mg, 2.6 mmol) in toluene (30 mL) at 0 °C under a nitrogen gas atmosphere and then the reaction mixture was stirred at 60 °C for overnight, monitored by TLC. The mixture was concentrated under reduced pressure, and the crude material was purified by silica gel column chromatography (EA: PE = 10: 1) to afford (9) (309 mg, 37%) as a white solid.LC-MS (ESI) m/z = 493 [M+H].

Reference： [1]Current Patent Assignee: TB ALLIANCE INC - WO2017/15106, 2017, A1 Location in patent: Page/Page column 138; 140

28
[ 264600-97-7 ]
C₂₂H₂₇FN₂O₈S [ No CAS ]
tert-butyl 4-((3S,3aS)-3-(((tert-butoxycarbonyl)(isoxazol-3-yl)amino)methyl)-8-fluoro-1-oxo-3a,4-dihydro-1H,3H-benzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl)-3,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: 3-N-(t-butoxycarbonyl)amino-1,2-isoxazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.0833333h; Stage #2: C₂₂H₂₇FN₂O₈S In N,N-dimethyl-formamide; mineral oil at 0 - 70℃; for 2h;
60%	In N,N-dimethyl-formamide at 70℃; for 2h;	7.1 Step 1: Preparation of tert-Butyl-4-((3S,3aS)-3-(((tert-butoxycarbonyl)(isoxazol-3-yl)amino)methyl)-8-fluoro-1-oxo-3a, 4-Dihydro-1H,3H-benzo[b]oxazole[3,4-d][1,4]oxazin-7-yl)-3,6-dihydropyridine-1(2H)-A Acid ester I-10-1 N-Boc-3-aminoisoxazole (0.37 g, 2.0 mmol) was dissolved in DMF (7 mL).After 5 minutes, tert-butyl-4-((3R,3aS)-3-(((methylsulfonyl)oxy)methyl)-8-fluoro-1-oxo-3a,4-dihydro-1H was added. ,3H-benzo[b]oxazole[3,4-d][1,4]oxazin-7-yl)-3,6-dihydropyridine-1(2H)-formate I-3- 1 (1.0 g, 2 mmol), and reacted at 70 ° C for 2 hours.After cooling, ice water (25 mL) was added dropwise, and ethyl acetate (20 mL×3) was evaporated. The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered, concentrated, silica gel (200-300 mesh) column chromatography, petroleum ether - A mixture of ethyl acetate (V: V = 3:2) was used as an eluent.Intermediate I-10-1,The pale yellow solid was 703 mg, yield 60.0%.

Reference： [1]Zhao, Hongyi; Lu, Yu; Sheng, Li; Yuan, Zishuo; Wang, Bin; Wang, Weiping; Li, Yan; Ma, Chen; Wang, Xiaoliang; Zhang, Dongfeng; Huang, Haihong [ACS Medicinal Chemistry Letters, 2017, vol. 8, # 5, p. 533 - 537]
[2]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN108239098, 2018, A Location in patent: Paragraph 0256; 0259-0261

29
[ 264600-97-7 ]
[ 264601-15-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / tetrahydrofuran / 4.5 h / 0 - 20 °C 2: N-ethyl-N,N-diisopropylamine / 0.17 h / 0 - 4 °C 3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 18 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US2003/207899, 2003, A1

30
[ 264600-97-7 ]
[ 264601-10-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / tetrahydrofuran / 4.5 h / 0 - 20 °C 2: N-ethyl-N,N-diisopropylamine / 0.17 h / 0 - 4 °C 3: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US2003/207899, 2003, A1

31
[ 264600-97-7 ]
5(R)-(N-isoxazol-3-yl-N-tertbutoxycarbonyl)-aminomethyl-3-(3,5-difluoro-4-(1-(2(S)-acetoxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)phenyl)-oxazolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / tetrahydrofuran / 4.5 h / 0 - 20 °C 2: N-ethyl-N,N-diisopropylamine / 0.17 h / 0 - 4 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US2003/207899, 2003, A1

32
[ 264600-97-7 ]
5(R)((N-isoxazol-3-yl-N-tertbutoxycarbonyl)aminomethyl)-3-(3,5-difluoro-4-(1,2,5,6-tetrahydropyrid-4-yl)phenyl)oxazolidin-2-one hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / tetrahydrofuran / 4.5 h / 0 - 20 °C 2: N-ethyl-N,N-diisopropylamine / 0.17 h / 0 - 4 °C

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US2003/207899, 2003, A1

33
[ 264600-97-7 ]
C₂₂H₂₀N₆O₉S [ No CAS ]
C₂₉H₂₈N₈O₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-N-(t-butoxycarbonyl)amino-1,2-isoxazole With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at -10℃; for 2h; Stage #2: C₂₂H₂₀N₆O₉S In N,N-dimethyl-formamide at 30℃;	3 In -10 °C lower, N - Boc - amino isoxazole (157.6 mg, 0 . 86mmol) of DMF (5 ml) solution is added into the T - BuOK (105.5 mg, 0 . 94mmol), stirring 2 hours. Adding intermediate 5 of DMF (3 ml), in the 30°CStirring overnight. For NH4Cl solution (20 ml) quenching, DCM (3x20 ml) extraction. The combined organic phase, salt water washing, drying. The solvent evaporate under the vacuum, crude product by column chromatography (DCM - MeOH) to obtain the product.

Reference： [1]Current Patent Assignee: MICURX PHARMACEUTICAL TECH SHANGHAI - CN106317072, 2017, A Location in patent: Paragraph 0078; 0080

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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
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H250	Catches fire spontaneously if exposed to air
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Health hazards
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H300	Fatal if swallowed
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H310	Fatal in contact with skin
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 264600-97-7 ]

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[ 264600-97-7 ] Synthesis Path-Downstream 1~33

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Isoxazoles

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