[ CAS No. 118994-89-1 ] Ethyl oxazole-5-carboxylate

Cat. No.: A127831

2D 3D

Structure of 118994-89-1 * Storage: Sealed in dry,2-8°C

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Quality Control of [ 118994-89-1 ]

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Product Details of [ 118994-89-1 ]

CAS No. :	118994-89-1	MDL No. :	MFCD04114930
Formula :	C₆H₇NO₃	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	KRMORCCAHXFIHF-UHFFFAOYSA-N
M.W :	141.12	Pubchem ID :	10964603
Synonyms :

Calculated chemistry of [ 118994-89-1 ] Expand+

Safety of [ 118994-89-1 ]

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

Application In Synthesis of [ 118994-89-1 ]

* 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 [ 118994-89-1 ]
Downstream synthetic route of [ 118994-89-1 ]

[ 118994-89-1 ] Synthesis Path-Upstream 1~1

1
[ 118994-89-1 ]
[ 127232-41-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.5 h;	A solution of 33 (29.13 g, 0.207 mol) in THF (206 mL) was added dropwise to a suspension of LiAlH₄ (7.85 g, 0.207 mmol) in THF (206 mL) at 0 °C. The reaction mixture was stirred for 30 min at 0 °C (at this point TLC indicated consumption of the SM) and quenched by successive addition of water (8 mL), 10percent NaOH (8 mL) solution, and water (24 mL). The temperature should not exceed 0 °C). The precipitate was filtered and washed several times with THF. The filtrate was evaporated to give 34, which was used without purification. M = 17.7 g. Yield = 86percent.
70%	With sodium tetrahydroborate In ethanol at 0 - 20℃;	Example A.8 Ethyl oxazole-5-carboxylate (1 g, 7.09 mmol, 1 eq) was dissolved in EtOH(l4mL) and the mixture was cooled to 0°C. Sodium borohydride (0.54 g, 14.1 7mmol, 2eq) was added portionwise while stirring, and then the mixture was allowed to warm to r.t.. After overnight stirring at r.t. the conversion was complete by TLC (95/5 DCM/MeOH). The mixture was cooled to 0°C and 2N HC1 was added dropwise till gas evolution ceased (pH 5-6). The obtained suspension was concentrated at reducedpressure, and the residue was purified by flash chromatography (5i02) using as eluent a mixture DCM/MeOH = 95/5. The pure intermediate (11) were obtained as colourless oil (0.49 g, yield 70percent).
58%	With sodium tetrahydroborate In ethanol at 0 - 20℃; for 16 h; Inert atmosphere	[000282] Synthesis of oxazol-5-ylmethanol (343): To a stirred solution of ethyl oxazole-5- carboxylate 342 (2 g, 14.18 mmol) in EtOH (20 mL) under argon atmosphere was added sodium borohydride (1.07 g, 28.36 mmol) at 0 °C; warmed to RT and stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was quenched with saturated ammonium chloride solution (25 mL) and extracted with 5percent MeOH/ CH2C12 (2 x 20 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 5percent MeOH/ CH2C12 to afford compound 343 (810 mg, 58percent) as colorless syrup. TLC: 5percent MeOH/ CH2C12 (R 0.3); 1H-NMR (DMSO-d6, 500 MHz): ö 8.28 (s, 1H), 7.04 (s, 1H), 5.36 (t, J 6.0 Hz, 1H), 4.47 (d, J 6.0 Hz, 2H).

Reference： [1] European Journal of Medicinal Chemistry, 2018, vol. 154, p. 367 - 391
[2] Tetrahedron Letters, 2006, vol. 47, # 4, p. 549 - 552
[3] Tetrahedron, 2008, vol. 64, # 21, p. 4778 - 4791
[4] Collection of Czechoslovak Chemical Communications, 2009, vol. 74, # 6, p. 887 - 900
[5] Patent: WO2015/118019, 2015, A1, . Location in patent: Page/Page column 35; 36
[6] Chemistry - A European Journal, 2007, vol. 13, # 19, p. 5515 - 5538
[7] Organic Letters, 2010, vol. 12, # 22, p. 5088 - 5091
[8] Patent: WO2015/138895, 2015, A1, . Location in patent: Paragraph 000282
[9] Patent: CN103848814, 2016, B, . Location in patent: Paragraph 0323-0325

[ 118994-89-1 ] Synthesis Path-Downstream 1~21

1
[ 924-44-7 ]
[ 38622-91-2 ]
[ 118994-89-1 ]

Yield	Reaction Conditions	Operation in experiment
54%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; toluene; at 0 - 20℃; for 3h;	INTERMEDIATE 171 - PREPARATION OF ethyl oxazole-5-carboxylate; 1 ,8-Diazabicyclo[5.4.0]undec-7-ene (0.574 ml 3.84 mmol) was added simultaneously with ethyl glyoxalate (50% in toluene, 0.659 ml 3.33 mmol) to a mixture of tosylmethyl isocyanide (0.500 g; 2.560 mmol) in dichloromethane (10 ml.) at 00C. The resulting mixture was stirred at room temperature for 3 hours, diluted in dichloromethane and washed with sodium hydrogen sulphate, sodium carbonate, dried over magnesium sulphate and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 5 to 60 % ethyl acetate in heptane) to yield 0.194 g (54 %) of ethyl oxazole-5-carboxylate as a colorless oil.ESI/APCI(+): 142(M+H).
51%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; toluene; at 0 - 20℃; for 8h;	To a stirred solution of TosMIC (50.0?g, 256?mmol) in CH2Cl2 (255?mL) was added ethyl glyoxylate (~50% in toluene, 56?mL, 283?mmol, 1.1 equiv). The solution was cooled to 0?C, and at this temperature, DBU (38?mL, 254?mmol) was added dropwise. The reaction mixture was allowed to warm to ambient temperature and stirred for 8?h. The reaction mixture was washed with water (~300?mL), organic layers was dried over Na2SO4 and evaporated. The residue was distilled at reduced pressure. bp?=?98?C (25?mbar). M?=?18.3?g. Yield?=?51%. 1H NMR: (CDCl3, 400?MHz) delta?=?1.35 (t, J?=?7.2?Hz, 3?H), 4.35 (q, J?=?7.1?Hz, 2?H), 7.73 (s, 1?H), 7.99 (s, 1?H). 13C NMR (CDCl3, 100?MHz): delta?=?14.2, 61.7, 133.3, 142.9, 153.3, 157.6.
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; toluene; at 0℃; for 1.33333h;Inert atmosphere;	All weights, volumes and equivalents are relative to toluenesulfonylmethyl isocyanide. Toluenesulfonylmethyl isocyanide (TosMIc) (12.31 g, 1 wt, 1 eq) is dissolved in DCM (61.6 ml, 5 vols) at 0 C under N2. In a seperate vessel, ethyl glyoxalate (50 wt% solution in toluene, 20.6 g, 20.0 ml, 1.67 wt) is diluted with DCM (61.6 ml, 5 vols) under N2 and DBU (12.48 g, 12.35 ml, 1.3 eq, 1.01 wt) is added resulting in a purple solution. The second solution is added to the TosMIc solution over 1 hr, maintaining temperature at 0 C, then checked by HPLC for completion after a further 20 mins. The reaction is quenched by slow addition of 2M HCI (10 vols, 123 ml) and the DCM layer separated. The aqueous layer is re-extracted with DCM (5 vols, 61.6 ml), and the combined organics dried over Na2S04, then evaporated on Buchi, 25 C, 100 mbar to remove DCM and toluene. Distilled at 12 mbar, jacket temperature 105 C, vapour temperature 60-80 C to afford ethyl oxazole-5-carboxylate as a colourless oil.

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; toluene; at 0℃; for 1.33333h;Inert atmosphere;

All weights, volumes and equivalents are relative to toluenesulfonylmethyl isocyanide.Toluenesulfonylmethyl isocyanide (TosMIc) (12.31 g, 1 wt, 1 eq) is dissolved in DCM (61.6 ml, 5 vols) at 0 C. under N2. In a seperate vessel, ethyl glyoxalate (50 wt % solution in toluene, 20.6 g, 20.0 ml, 1.67 wt) is diluted with DCM (61.6 ml, 5 vols) under N2 and DBU (12.48 g, 12.35 ml, 1.3 eq, 1.01 wt) is added resulting in a purple solution. The second solution is added to the TosMIc solution over 1 hr, maintaining temperature at 0 C., then checked by HPLC for completion after a further 20 mins. The reaction is quenched by slow addition of 2M HCl (10 vols, 123 ml) and the DCM layer separated. The aqueous layer is re-extracted with DCM (5 vols, 61.6 ml), and the combined organics dried over Na2SO4, then evaporated on Buchi, 25 C., 100 mbar to remove DCM and toluene. Distilled at 12 mbar, jacket temperature 105 C., vapour temperature 60-80 C. to afford ethyl oxazole-5-carboxylate as a colourless oil.

Reference： [1]Collection of Czechoslovak Chemical Communications,2009,vol. 74,p. 887 - 900
[2]Tetrahedron Letters,2006,vol. 47,p. 549 - 552
[3]Chemistry - A European Journal,2007,vol. 13,p. 5515 - 5538
[4]Organic Letters,2010,vol. 12,p. 5088 - 5091
[5]Patent: WO2010/142801,2010,A1 .Location in patent: Page/Page column 200
[6]European Journal of Medicinal Chemistry,2018,vol. 154,p. 367 - 391
[7]Patent: WO2012/32067,2012,A1 .Location in patent: Page/Page column 60
[8]Patent: US2013/203772,2013,A1 .Location in patent: Paragraph 0324; 0325; 0326

2
[ 118994-89-1 ]
[ 127232-41-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 0.5h;	A solution of 33 (29.13?g, 0.207?mol) in THF (206?mL) was added dropwise to a suspension of LiAlH4 (7.85?g, 0.207?mmol) in THF (206?mL) at 0?C. The reaction mixture was stirred for 30?min?at 0?C (at this point TLC indicated consumption of the SM) and quenched by successive addition of water (8?mL), 10% NaOH (8?mL) solution, and water (24?mL). The temperature should not exceed 0?C). The precipitate was filtered and washed several times with THF. The filtrate was evaporated to give 34, which was used without purification. M?=?17.7?g. Yield?=?86%.
70%	With sodium tetrahydroborate; In ethanol; at 0 - 20℃;	Example A.8 Ethyl oxazole-5-carboxylate (1 g, 7.09 mmol, 1 eq) was dissolved in EtOH(l4mL) and the mixture was cooled to 0C. Sodium borohydride (0.54 g, 14.1 7mmol, 2eq) was added portionwise while stirring, and then the mixture was allowed to warm to r.t.. After overnight stirring at r.t. the conversion was complete by TLC (95/5 DCM/MeOH). The mixture was cooled to 0C and 2N HC1 was added dropwise till gas evolution ceased (pH 5-6). The obtained suspension was concentrated at reducedpressure, and the residue was purified by flash chromatography (5i02) using as eluent a mixture DCM/MeOH = 95/5. The pure intermediate (11) were obtained as colourless oil (0.49 g, yield 70%).
64%	With sodium tetrahydroborate; In tetrahydrofuran; at 0 - 25℃; for 49h;	Step 7: Preparation of oxazol-5-ylmethanol. [0747] To a solution of <strong>[118994-89-1]ethyl oxazole-5-carboxylate</strong> (2.00 g, 14.2 mmol) in THF (20 mL) was added NaBTU (1.07 g, 28.3 mmol) at 0 C and then the mixture was stirred at 25 C for 48 h. A white cloudy was formed. To the mixture was added anhydrous Na2S04 (20 g) and the mixture was stirred at 25 C for 1 hour. The mixture was filtered and the cake was washed with MTBE (20 mL). The combined organic layer was concentrated to dryness. The residue was purified by Combi Flash (EtOAc in pentane from 10% to 100%) to give oxazol-5-ylmethanol (900 mg, 64% yield) as colorless oil. NMR (400 MHz, CDCb) d 2.02 (1H, brt, J= 6.0 Hz), 4.74 (2H, d, J= 6.0 Hz), 7.06 (1H, s), 7.89 (1H, s).

58%	With sodium tetrahydroborate; In ethanol; at 0 - 20℃; for 16h;Inert atmosphere;	[000282] Synthesis of oxazol-5-ylmethanol (343): To a stirred solution of ethyl oxazole-5- carboxylate 342 (2 g, 14.18 mmol) in EtOH (20 mL) under argon atmosphere was added sodium borohydride (1.07 g, 28.36 mmol) at 0 C; warmed to RT and stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was quenched with saturated ammonium chloride solution (25 mL) and extracted with 5% MeOH/ CH2C12 (2 x 20 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 5% MeOH/ CH2C12 to afford compound 343 (810 mg, 58%) as colorless syrup. TLC: 5% MeOH/ CH2C12 (R 0.3); 1H-NMR (DMSO-d6, 500 MHz): oe 8.28 (s, 1H), 7.04 (s, 1H), 5.36 (t, J 6.0 Hz, 1H), 4.47 (d, J 6.0 Hz, 2H).
	With sodium tetrahydroborate; ethanol; calcium chloride; In tetrahydrofuran; at 0℃;	At 0 under ice-cooling, the solution containing oxazole-5-carboxylate (3.57g, 25.0mmol) in 50mL of ethanol and 50mL of THF was added anhydrous CaCl2(11.1g, 100.0mmol), and stirred until the solid completely dissolved, then the solution was added portionwise NaBH4(2.70g, 71.0mmol).The reaction overnight, the reaction end point detection LCMS, after completion of the reaction, the mixed solution was added saturated NH4Cl solution, and extracted three times of dichloromethane was added 30mL liquid separation, the organic phases combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to dryness to give a crude product 1.98g of 5-hydroxymethyl isoxazole, a yield of 80%.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 154,p. 367 - 391
[2]Tetrahedron Letters,2006,vol. 47,p. 549 - 552
[3]Collection of Czechoslovak Chemical Communications,2009,vol. 74,p. 887 - 900
[4]Patent: WO2015/118019,2015,A1 .Location in patent: Page/Page column 35; 36
[5]Chemistry - A European Journal,2007,vol. 13,p. 5515 - 5538
[6]Patent: WO2019/126731,2019,A1 .Location in patent: Paragraph 0747
[7]Organic Letters,2010,vol. 12,p. 5088 - 5091
[8]Patent: WO2015/138895,2015,A1 .Location in patent: Paragraph 000282
[9]Patent: CN103848814,2016,B .Location in patent: Paragraph 0323-0325

3
[ 118994-89-1 ]
5-ethoxycarbonyl-[2,4']bisoxazole [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 3351 - 3354

4
[ 118994-89-1 ]
2-[isocyano-(toluene-4-sulfonyl)-methyl]-oxazole-5-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 3351 - 3354

5
[ 33763-20-1 ]
[ 118994-89-1 ]
[ 1227747-47-8 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 2768 - 2771

6
[ 118994-89-1 ]
2,4-diiodo-5-carbethoxyoxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of ethyl 1 ,3-oxazole-5-carboxylate (0.86 g, 6.07 mmol) in THF (12,2 mL) at -40 0C were added potassium hexamethyldisilylazide (0.5 M; 14.6 niL, 7.29 mmol). After 1 h, a solution of iodine (3.85 g, 15.2 mmol) in THF (8 mL) was slowly added over 15 min. The mixture was stirred at -40 0C for 1 h then allowed to warm to ambient temperature. Sat. NaHCtheta3 and sat. Na2SC^ were added and the mixture was extracted with dchloromethane (3x). The combined organic extracts was dried over MgSO4, filtered and concentrated. Purification by silica gel chromatography (100% hexanes - » 90 % hexanes/ ethyl acetate) gave the title compound (0.86 g, 32% pure).

Reference： [1]Patent: WO2010/111059,2010,A1 .Location in patent: Page/Page column 60

7
[ 118994-89-1 ]
[ 1258283-17-8 ]

Yield	Reaction Conditions	Operation in experiment
30%	With bromine; lithium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide; at -60℃; for 4h;	To a solution of <strong>[118994-89-1]ethyl oxazole-5-carboxylate</strong> (0.28 g, 2.00 mmol) in THF/DMF (2/2 mL) was added Br2 (0.13 mL, 2.6 mmol, 1.3 eq.) and LHMDS (2.6 mL 2.6 mmol, 1.3 eq) to obtain a reaction mixture, which was stirred at -60 C. for 4 hours. The reaction mixture was extracted with EA and water and the combined organic layer was dried with MgSO4. The residue was purified by flash chromatography with EA/Hex (EA/Hex=1:4) to give OS-a.1 as yellow oil (0.1 g, 30%).
		4-bromo<strong>[118994-89-1]oxazole-5-carboxylic acid ethyl ester</strong>To a solution of <strong>[118994-89-1]oxazole-5-carboxylic acid ethyl ester</strong> (12.2 g) in a mixture of tetrahydrofuran (70 ml.) and 1 ,3-dimethyl-3,4,5,6-tetrahydro-2(1 H)-pyrimidinone (70 ml.) was added, over 30 minutes at -65 to -78C under nitrogen, a 1.0 M solution of 1 ,1 ,1 ,3,3,3-hexamethyldisilazane lithium salt in tetrahydrofuran (110 ml_). The solution was stirred at -780C for 80 minutes, then bromine (5.8 ml_) was added dropwise over 20 minutes and the resulting mixture was stirred at -780C for a further 45 minutes. The cold solution was added to a mixture of te/t-butylmethyl ether (50O mL) and 10% aqueous sodium thiosulfate solution (500 ml_) at room temperature. The phases were separated and the organic layer was washed with water and brine, then dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of diethyl ether and pentane (0:1 to 1 :1 by volume), to afford the title compound (2.44 g) as a solid mass.MS: ESI (+ve) (Method E): 220 (M+H)+, Retention time 3.27 min.
	With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; bromine;	Ethyl 4-bromooxazole-5-carboxylate (2) To a solution of <strong>[118994-89-1]ethyl oxazole-5-carboxylate</strong> (1) (100.0 g, 0.71 mol) in THF (500 mL) and DMPU (500 mL) was added LiHMDS (1.0 M, 921 mL, 921 mmol) dropwise at -78 C. under N2 atmosphere, and the mixture was stirred for 1.5 hours. Then Br2 (54.5 mL, 1.06 mol) was added dropwise at the same temperature and the resulting mixture was stirred for 0.5 hours. TLC showed the starting material disappeared. The resulting solution was poured into a room temperature saturated aqueous NH4Cl (1000 mL), extracted with EtOAc (500 mL3). The combined organic layers were washed with brine (500 mL2), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by MPLC to give ethyl 4-bromooxazole-5-carboxylate (25.0 g, purity: 90%, yield: 11%) as yellow oil. 1H NMR (400 MHz, CHCl3-d): delta 7.94 (s, 1H), 4.43 (q, J=7.3 Hz, 2H), 1.42 (t, J=7.2 Hz, 3H)

Reference： [1]Patent: US2019/352288,2019,A1 .Location in patent: Paragraph 0663-0664
[2]Patent: WO2010/142934,2010,A1 .Location in patent: Page/Page column 27
[3]Patent: US2020/123117,2020,A1

8
[ 118994-89-1 ]
2-iodo-5-carbethoxyoxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%		LiHMDS (1M solution, 15 mL, 15.0 mmol) was added at -78 C to a solution of <strong>[118994-89-1]ethyl 5-oxazolecarboxylate</strong> [118994-89-1] (1.26 mL, 10.0 mmol) in THF (50 mL). The reaction mixture was stirred at -78 C for 1 h and ZnCl2 (0.7M solution, 22.8 mL, 16.0 mmol) was added drop wise. The reaction mixture was warmed to room temperature and stirred for 30 min. A solution of I2 (5.13 g, 20.0 mmol) in THF (5 mL) was added drop wise at -78 C. The reaction mixture was stirred at -78 C for 15 min and at room temperature for 1 h. The mixture was diluted with Na2S203 (sat., aq.) and extracted with Et20 (twice). The combined organic extracts were dried (MgS04), filtered and concentrated in vacuo. The crude mixture was purified by flash column chromatography (silica, heptane/EtOAc, gradient from 100:0 to 95:5) to afford 1-159 (2.2 g, 82%).
42%		To a solution of 1 ,3-oxazole-5-carboxylate (1.02 g, 7.17 mmol) in THF (25 ml.) at - 78 0C was added LHMDS (7.53 ml_, 7.53 mmol). After 1 hour, a solution of diiodoethane (1.04 ml_, 7.88 mmol) in THF (10 ml.) was added over 15 minutes. The mixture was stirred for an additional 1 hr at -78 0C and warmed to room temperature. The mixture was poured onto cold Et2O (200 ml.) and 10% Na2S2O3 (200 ml_). The organic layer was separated, dried over Na2SO4 and purified via column chromatography (silica, 0 - 40% EtOAc/hexanes) affording the product as a white solid (805 mg, 42%).

Reference： [1]Patent: WO2019/243535,2019,A1 .Location in patent: Page/Page column 82-83
[2]Patent: WO2009/158372,2009,A1 .Location in patent: Page/Page column 34; 35

9
[ 118994-89-1 ]
[ 1202632-49-2 ]

Reference： [1]Patent: WO2009/158372,2009,A1

10
[ 617-84-5 ]
[ 118994-89-1 ]
[ 1326303-44-9 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 8946 - 8948

11
[ 1254036-94-6 ]
[ 118994-89-1 ]
[ 1254036-81-1 ]

Yield	Reaction Conditions	Operation in experiment
		Method DAll weights, volumes and equivalents are relative to 6-chloro-4-iodo-1-(phenylsulfonyl)-1 H- indazole.Zinc chloride (3.6 eq, 1.17 wt, 52.7 g) in tetrahydrofuran (5 vols, 225 ml) is cooled to 0 to 5 C. A solution of the <strong>[118994-89-1]ethyl oxazole-5-carboxylate</strong> (1.1 eq, 0.37 wt, 18.1 g, corrected for 92 wt% assay) in tetrahydrofuran (5 vols, 225 ml) is added to the vessel. The suspension is cooled to -10 C (+/-5 C) under a nitrogen atmosphere and a 1 M solution of bis- (trimethylsilyl)-lithiumamide in tetrahydrofuran (1.80 eq, 4.30 vols, 193 ml) is added over 15 minutes maintaining the temperature at -10 C (+/-5 C). The resulting solution is stirred under a nitrogen atmosphere at -10 C (+/-5 C) for 1 hour. To the solution is added 6-chloro-4-iodo-1-(phenylsulfonyl)-1 H-indazole (1.0 eq, 1.0 wt, 45.0 g) and tetrakis triphenylphosphine palladium (0.03 eq, 0.083 wt, 3.73 g) (the mixture is degassed with vacuum/nitrogen 3 times) and then heated to 60C (+/-3C) for at least 6 hours. The reaction is then checked by HPLC for completion. The reaction solution is cooled to 0 C (+/-3 C) and a solution of 25% w/w diisobutylaluminium hydride in toluene (4.0 eq, 6.4 vols, 288 ml) is added maintaining the temperature at <5C. The resulting reaction solution is then stirred at 0C (+/-3C) for at least 1 hour. The reaction is then checked by HPLC (generic) for completion. The reaction mixture is added portion wise to a solution of citric acid (4.0 eq, 2.0 wt, 90 g) in water (10 vols, 450 ml) at 0 C (+/-5 C) over ~1 h. The resulting solution is stirred at 20 C for 15 minutes, extracted with ethyl acetate (10 vols, 450 ml), the organic layer is washed with water (2 x 3 vols, 2 x 135 ml) and filtered through a porosity 4 sinter. The organic layer is then evaporated under reduced pressure (45 C, 100 mbar) to 2 to 3 volumes, dimethyl sulphoxide (10 vols, 450 ml) is added and the solution evaporated under reduced pressure (45 C, 50 mbar) to remove all traces of other solvents. To the solution at 45 C is added water (5 vols, 225 ml) dropwise over 30 minutes, the resulting reaction mixture is cooled to 20 C over 3hr and stirred at 20 C for at least 15 hrs. The product is filtered, washed with a solution of dimethylsulphoxide:water (1 :2) (2 vols, 90 ml), then washed with water (3 vols, 135 ml), then dried under high vacuum at 60 C (+/-3 C) to constant probe temperature to afford (2-(6-chloro-1- (phenylsulfonyl)-1 H-indazol-4-yl)oxazol-5-yl)methanol as a beige solid.

Reference： [1]Patent: WO2012/32067,2012,A1 .Location in patent: Page/Page column 50-51

12
[ 25563-06-8 ]
[ 118994-89-1 ]
[ 1037597-71-9 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 4214 - 4216

13
[ 924-44-7 ]
1-((isocyanomethyl)sulfonyl)-2-methylbenzene [ No CAS ]
[ 118994-89-1 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0℃;Inert atmosphere;	8Ethyl oxazole-5-carboxylateAll weights, volumes and equivalents are relative to toluenesulfonylmethyl isocyanide.Toluenesulfonylmethyl isocyanide (TosMIc) (12.31 g, 1 wt, 1 eq) is dissolved in DCM (61 .6 ml, 5 vols) at 0 C under N2. In a seperate vessel, ethyl glyoxalate (50 wt% solution in toluene, 20.6 g, 20.0 ml, 1.67 wt) is diluted with DCM (61 .6 ml, 5 vols) under N2 and DBU (12.48 g, 12.35 ml, 1.3 eq, 1.01 wt) is added resulting in a purple solution. The second solution is added to the TosMIc solution over 1 hr, maintaining temperature at 0 C, then checked by HPLC for completion after a further 20 mins. The reaction is quenched by slow addition of 2M HCI (10 vols, 123 ml) and the DCM layer separated. The aqueous layer is re-extracted with DCM (5 vols, 61.6 ml), and the combined organics dried over Na2S04, then evaporated on Buchi, 25 C, 100 mbar to remove DCM and toluene. Distilled at 12 mbar, jacket temperature 105 C, vapour temperature 60-80 C to afford ethyl oxazole-5-carboxylate as a colourless oil.
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; toluene; at 0℃; for 1.33333h;Inert atmosphere;	Ethyl oxazole-5-carboxylate All weights, volumes and equivalents are relative to toluenesulfonylmethyl isocyanide. Toluenesulfonylmethyl isocyanide (TosMIc) (12.31 g, 1 wt, 1 eq) is dissolved in DCM (61.6 ml, 5 vols) at 0 C. under N2. In a separate vessel, ethyl glyoxalate (50 wt % solution in toluene, 20.6 g, 20.0 ml, 1.67 wt) is diluted with DCM (61.6 ml, 5 vols) under N2 and DBU (12.48 g, 12.35 ml, 1.3 eq, 1.01 wt) is added resulting in a purple solution. The second solution is added to the TosMIc solution over 1 hr, maintaining temperature at 0 C., then checked by HPLC for completion after a further 20 mins. The reaction is quenched by slow addition of 2M HCl (10 vols, 123 ml) and the DCM layer separated. The aqueous layer is re-extracted with DCM (5 vols, 61.6 ml), and the combined organics dried over Na2SO4, then evaporated on Buchi, 25 C., 100 mbar to remove DCM and toluene. Distilled at 12 mbar, jacket temperature 105 C., vapour temperature 60-80 C. to afford ethyl oxazole-5-carboxylate as a colourless oil.

Reference： [1]Patent: WO2012/55846,2012,A1 .Location in patent: Page/Page column 55-56
[2]Patent: US9326987,2016,B2 .Location in patent: Page/Page column 165

14
[ 118994-89-1 ]
[ 158178-93-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	In methanol; ammonia;liquid NH3;	Step A: Oxazole-5-carboxamide Ethyl oxazole-5-carboxylate (2 g, 14.2 mmol) was dissolved in NH3 solution (7 M in MeOH, 25 mL). The solution was stirred at room temperature for 2 hr and filtered. The solid was dried to give the desired product (1.5 g, 92% yield) as a white powder which was used directly in the next step.
92%	With ammonia; In methanol; at 20℃; for 2h;	Example 17. Preparation of (S)-N-((S)-l-(2-chlorophenyl)-2-((3,3- difluorocyclobutyl)amino)-2-oxoethyl)-l-(5-cyanooxa-zol-2-yl)-N-(3,5-difluorophenyl)-5- oxopyrrolidine-2-carboxamide (sin le enantiomer) - Compound 162 Step A : Oxazole-5-carboxamide. Ethyl oxazole-5-carboxylate (2 g, 14.2 mmol) was dissolved in NH3 solution (7 M in MeOH, 25 mL). The solution was stirred at room temperature for 2 hr and filtered. The solid was dried to give the desired product (1.5 g, 92% yield) as a white powder which was used directly in the next step.
92%	In ammonia;liquid NH3;	Step A: Oxazole-5-carboxamide Ethyl oxazole-5-carboxylate (2 g, 14.2 mmol) was dissolved in NH3 solution (7 M in MeOH, 25 mL). The solution was stirred at room temperature for 2 hr and filtered. The solid was dried to give the desired product (1.5 g, 92% yield) as a white powder which was used directly in the next step.

92%	With ammonia; In methanol; at 20℃; for 2h;	Ethyl oxazole-5-carboxylate (2 g, 14.2 mmol) was dissolved in NH3 solution (7M in MeOH, 25 mL). The solution was stirred at room temperature for 2hr and filtered. The solid was dried to give the desired product (1.5 g, 92% yield) as a whitepowder which was used directly in the next step.
92%	With ammonia; In methanol; at 20℃; for 2h;	Step A .- Oxazole-5-carboxamide. Ethyl oxazole-5-carboxylate (2 g, 14.2 mmol) was dissolved in NH3 solution (7 M in MeOH, 25 mL). The solution was stirred at room temperature for 2 hr and filtered. The solid was dried to give the desired product ( 1 .5 g, 92% yield) as a white powder which was used directly in the next step.

Reference： [1]Patent: US2013/190249,2013,A1 .Location in patent: Page/Page column
[2]Patent: WO2013/107291,2013,A1 .Location in patent: Page/Page column 146
[3]Patent: US2015/31627,2015,A1 .Location in patent: Page/Page column
[4]Patent: WO2015/10626,2015,A1 .Location in patent: Page/Page column 145; 146
[5]Patent: WO2015/10297,2015,A1 .Location in patent: Page/Page column 146

15
[ 142-29-0 ]
[ 118994-89-1 ]
[ 15524-48-8 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3550 - 3553

16
[ 1254036-94-6 ]
[ 118994-89-1 ]
[ 1254036-83-3 ]

Yield	Reaction Conditions	Operation in experiment
		All weights, volumes and equivalents are relative to 6-chloro-4-iodo-1-(phenylsulfonyl)-1H-indazole.Zinc chloride (3.6 eq, 1.17 wt, 52.7 g) in tetrahydrofuran (5 vols, 225 ml) is cooled to 0 to 5 C. A solution of the <strong>[118994-89-1]ethyl oxazole-5-carboxylate</strong> (1.1 eq, 0.37 wt, 18.1 g, corrected for 92 wt % assay) in tetrahydrofuran (5 vols, 225 ml) is added to the vessel. The suspension is cooled to -10 C. (+/-5 C.) under a nitrogen atmosphere and a 1M solution of bis-(trimethylsilyl)-lithiumamide in tetrahydrofuran (1.80 eq, 4.30 vols, 193 ml) is added over 15 minutes maintaining the temperature at -10 C. (+/-5 C.). The resulting solution is stirred under a nitrogen atmosphere at -10 C. (+/-5 C.) for 1 hour. To the solution is added 6-chloro-4-iodo-1-(phenylsulfonyl)-1H-indazole (1.0 eq, 1.0 wt, 45.0 g) and tetrakis triphenylphosphine palladium (0.03 eq, 0.083 wt, 3.73 g) (the mixture is degassed with vacuum/nitrogen 3 times) and then heated to 60 C. (+/-3 C.) for at least 6 hours. The reaction is then checked by HPLC for completion. The reaction solution is cooled to 0 C. (+/-3 C.) and a solution of 25% w/w diisobutylaluminium hydride in toluene (4.0 eq, 6.4 vols, 288 ml) is added maintaining the temperature at . The resulting reaction solution is then stirred at 0 C. (+/-3 C.) for at least 1 hour. The reaction is then checked by HPLC (generic) for completion. The reaction mixture is added portion wise to a solution of citric acid (4.0 eq, 2.0 wt, 90 g) in water (10 vols, 450 ml) at 0 C. (+/-5 C.) over 1 h. The resulting solution is stirred at 20 C. for 15 minutes, extracted with ethyl acetate (10 vols, 450 ml), the organic layer is washed with water (2×3 vols, 2×135 ml) and filtered through a porosity 4 sinter. The organic layer is then evaporated under reduced pressure (45 C., 100 mbar) to 2 to 3 volumes, dimethyl sulphoxide (10 vols, 450 ml) is added and the solution evaporated under reduced pressure (45 C., 50 mbar) to remove all traces of other solvents. To the solution at 45 C. is added water (5 vols, 225 ml) dropwise over 30 minutes, the resulting reaction mixture is cooled to 20 C. over 3 hr and stirred at 20 C. for at least 15 hrs. The product is filtered, washed with a solution of dimethylsulphoxide:water (1:2) (2 vols, 90 ml), then washed with water (3 vols, 135 ml), then dried under high vacuum at 60 C. (±3 C.) to constant probe temperature to afford (2-(6-chloro-1-(phenylsulfonyl)-1H-indazol-4-yl)oxazol-5-yl)methanol as a beige solid.
		All weights, volumes and equivalents are relative to6-chioro-4-iodo-1 -(phenylsulfonyl)-1 H-indazole.Zinc chloride (3.6 eq, 1.17 wt, 52.7 g) intetrahydrofuran (5 vols, 225 ml) is cooled to 0 to 5 C. A solution of the <strong>[118994-89-1]ethyl oxazole-5-carboxylate</strong> (1.1 eq, 0.37 wt, 18.1 g, corrected for92 wt % assay) in tetrahydroffiran (5 vols, 225 ml) is added tothe vessel. The suspension is cooled to -10 C. (+1-5 C.) under a nitrogen atmosphere and a 1M solution of bis-(trimethylsilyl)-lithiumamide in tetrahydrofuran (1.80 eq, 4.30vols, 193 ml) is added over 15 minutes maintaining the temperature at - 10C. (+ 1-5C.). The resulting solution is stirredunder a nitrogen atmosphere at -10 C. (+1-5 C.) for 1 hour. To the solution is added 6-chioro-4-iodo-1 -(phenylsulfonyl)1H-indazole (1.0 eq, 1.0 wt, 45.0 g) and tetrakis triphenylphosphine palladium (0.03 eq, 0.083 wt, 3.73 g) (themixture is degassed with vacuumlnitrogen 3 times) and then heated to 60 C. (+ 1-3 C.) for at least 6 hours. The reactionis then checked by HPLC for completion. The reaction solution is cooled to 0 C. (+1-3 C.) and a solution of 25% wlwdiisobutylaluminium hydride in toluene (4.0 eq, 6.4 vols, 288ml) is added maintaining the temperature at <5 C. The resulting reaction solution is then stirred at 0 C. (+1-3 C.) for atleast 1 hout The reaction is then checked by HPLC (generic) for completion. The reaction mixture is added portion wise toa solution of citric acid (4.0 eq, 2.0 wt, 90 g) in water (10 vols, 450 ml) at 0 C. (+1-5 C.) over 1 h. The resulting solutionis stirred at 20 C. for 15 minutes, extracted with ethyl acetate (10 vols, 450 ml), the organic layer is washed with water (2x3vols, 2x135 ml) and filtered through a porosity 4 sintet The organic layer is then evaporated under reduced pressure (45C., 100 mbar) to 2 to 3 volumes, dimethyl sulphoxide (10 vols, 450 ml) is added and the solution evaporated under reduced pressure (45 C., 50 mbar) to remove all traces ofother solvents. To the solution at 45 C. is added water (5 vols,225 ml) dropwise over 30 minutes, the resulting reactionmixture is cooled to 20 C. over 3 hr and stirred at 20 C. for at least 15 hrs. The product is filtered, washed with a solution of dimethylsulphoxide:water (1:2) (2 vols, 90 ml), thenwashed with water (3 vols, 135 ml), then dried under highvacuum at 60 C. (±3 C.) to constant probe temperature toafford (2-(6-chloro- 1 -(phenylsulfonyl)- 1 H-indazol-4-yl)ox- azol-5-yl)methanol as a beige solid.

Reference： [1]Patent: US2013/203772,2013,A1 .Location in patent: Paragraph 0289; 0298; 0299
[2]Patent: US9326987,2016,B2 .Location in patent: Page/Page column 128

17
[ 611-73-4 ]
[ 118994-89-1 ]
ethyl 2-benzoyloxazole-5-carboxylate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 7241 - 7244
[2]Journal of Organic Chemistry,2015,vol. 80,p. 11065 - 11072

18
[ 552-16-9 ]
[ 118994-89-1 ]
C₁₂H₁₀N₂O₅ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 7586 - 7589

19
[ 118994-89-1 ]
C₁₁H₁₇N₃O₃ [ No CAS ]

Reference： [1]Patent: WO2015/116663,2015,A1

20
[ 26218-78-0 ]
[ 118994-89-1 ]
methyl 2-(5-ethoxycarbonyloxazol-2-yl)pyridine-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With 1-Adamantanecarboxylic acid; palladium diacetate; potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate; In toluene; at 110℃; for 8h;Inert atmosphere;	j0238] Procedure:10239] Pd(OAc)2 (31.8 mg, 0.14 mmoles), [P(t-13u)3H] HF4 (123.2 mg, 0.42 mmoles), 1-adamantanecarboxylic acid (153 mg, 0.85 mmoles), K2C03 (782 mg, 5.7 mmoles), and methyl 6-bromonicotinate (918mg, 4.3 mmoles) were added to a dried flask. The flask was fitted with a reflux condenser capped with a septum, evacuated, and purged with nitrogen (.-5 times). A degassed solution of ethyl oxazole-5-carboxy- late (400 mg, 2.8 mmoles) in dry toluene (7 mE) was added via syringe, and the reaction was stirred at 1100 C. for 8 h. The reaction mixture was cooled and filtered through Celite, and the filtrate was concentrated under reduced pressure. The crude product was then purified by chromatography on silica (30% EtOAc in hexanes followed by 2% acetone in 1:1 DCM:hexanes) to afford the title compound (183 mg, 23%) as a white solid. ?H NMR (400 MHz, CDC13) oe 9.37 (dd, J=0.8, 2.0 Hz, 1H), 8.47 (dd, J=2.0, 8.0 Hz, 1H), 8.30 (dd, J=0.8, 8 Hz, 1H), 7.96 (s, 1H), 4.46 (q, J=7.2 Hz, 2H), 4.00 (s, 3H), 1.43 (t, J=7.2 Hz, 3H); ?3C NMR (100 MHz, CDC13) oe 164.9, 161.6, 157.5, 151.5, 148.0, 143.8, 138.3, 135.5, 127.3, 122.5, 61.9, 52.7, 14.3; HRMS (ESI) mlz 277.0823 [calc?d for C,3H,3N205 (M+H) 279.0819]. For experiments with mammalian cells, this compound was recrystallized from EtOAc to afford a white crystalline solid

Reference： [1]Patent: US2016/280701,2016,A1 .Location in patent: Paragraph 0237; 0238; 0239

21
[ 26218-78-0 ]
[ 118994-89-1 ]
methyl 2-(4-ethoxycarbonyloxazol-2-yl)pyridine-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With 3,3-dimethyl-butan-2-one; palladium diacetate; potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate; In toluene; at 110℃; for 24h;Inert atmosphere;	j0241] Procedure:j0242] Pd(OAc)2 (15.9 mg, 0.071 mmoles), [P(t-Hu)3H] HF4 (61.8 mg, 0.21 mmoles), pivalic acid (29.0 mg, 0.28 mmoles), K2C03 (391 mg, 2.8 mmoles), ethyl oxazole-4- carboxylate (200 mg, 1.4 mmoles), and methyl 6-bromoni- cotinate (612 mg, 2.8 mmoles) were added to a dried flask. The flask was fitted with a reflux condenser capped with a septum, evacuated, and purged with nitrogen (.-5 times). Drytoluene (7 mE) was added via syringe, and the reaction was stirred at 1100 C. for 24 h. The reaction mixture was cooled and filtered through Celite, and the filtrate was concentrated under reduced pressure. The crude product was then purified via chromatography on silica (2% acetone in DCM followed by 10% acetone 1:1 DCM:hexanes) to afford the title compound (113 mg, 29%) as a white solid. ?H NMR (400 MHz, CDC13) oe 9.31 (dd, J=0.8, 2.0 Hz, 1H), 8.46 (dd, J=2.0, 8.4 Hz, 1H), 8.42 (s, 1H), 8.38 (dd, J=0.8, 8.4 Hz, 1H), 4.45 (q, J=7.2 Hz, 2H), 4.00 (s, 3H), 1.42 (t, J=7.2 Hz, 3H); ?3C NMR (100 MHz, CDC13) oe 164.9, 160.8, 160.2,151.1, 148.0, 145.2, 138.3, 135.3, 127.1, 122.3, 61.6, 52.7, 14.3; HRMS (ESI) mlz 277.0815 [calc?d for C,3H,3N205 (M+H) 277.0823].

Reference： [1]Patent: US2016/280701,2016,A1 .Location in patent: Paragraph 0240; 0241; 0242

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Technical Information

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Num. heavy atoms :	10
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	32.59
TPSA :	52.33 Å²

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) :	-6.53 cm/s

Log Po/w (iLOGP) :	1.76
Log Po/w (XLOGP3) :	0.89
Log Po/w (WLOGP) :	0.85
Log Po/w (MLOGP) :	-0.43
Log Po/w (SILICOS-IT) :	0.94
Consensus Log Po/w :	0.8

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

Log S (ESOL) :	-1.45
Solubility :	5.03 mg/ml ; 0.0357 mol/l
Class :	Very soluble
Log S (Ali) :	-1.57
Solubility :	3.77 mg/ml ; 0.0267 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.69
Solubility :	2.86 mg/ml ; 0.0203 mol/l
Class :	Soluble

[ CAS No. 118994-89-1 ] Ethyl oxazole-5-carboxylate

Quality Control of [ 118994-89-1 ]

Related Doc. of [ 118994-89-1 ]

Product Details of [ 118994-89-1 ]

Calculated chemistry of [ 118994-89-1 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 118994-89-1 ]

Application In Synthesis of [ 118994-89-1 ]

[ 118994-89-1 ] Synthesis Path-Upstream 1~1

[ 118994-89-1 ] Synthesis Path-Downstream 1~21

Technical Information

Related Functional Groups of
[ 118994-89-1 ]

Esters

Related Parent Nucleus of
[ 118994-89-1 ]

Oxazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.09

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed

[ CAS No. 118994-89-1 ] Ethyl oxazole-5-carboxylate

Quality Control of [ 118994-89-1 ]

Related Doc. of [ 118994-89-1 ]

Product Details of [ 118994-89-1 ]

Calculated chemistry of [ 118994-89-1 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 118994-89-1 ]

Application In Synthesis of [ 118994-89-1 ]

[ 118994-89-1 ] Synthesis Path-Upstream 1~1

[ 118994-89-1 ] Synthesis Path-Downstream 1~21

Technical Information

Related Functional Groups of [ 118994-89-1 ]

Esters

Related Parent Nucleus of [ 118994-89-1 ]

Oxazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 118994-89-1 ]

Related Parent Nucleus of
[ 118994-89-1 ]