There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.
Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 216959-34-1 | MDL No. : | MFCD01631201 |
Formula : | C9H15NO5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DSDQWJVXMDHQLK-UHFFFAOYSA-N |
M.W : | 217.22 | Pubchem ID : | 2733665 |
Synonyms : |
|
Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P260-P264-P273-P301+P312-P305+P351+P338-P314 | UN#: | 3077 |
Hazard Statements: | H302-H319-H372-H410 | Packing Group: | Ⅲ |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; | (E)-N-t-Butoxycarbonyl-N-(ethoxyoxoacetyl)-4-(tert-butyldiphenylsilanyloxy)-2-fluoro-2-butenylamine To a cooled solution of (E)-N-t-butoxycarbonyl-2-fluoro-4-(3-methoxyphenoxy)-2-butenylamine (0.42 g, 1.22 mmol), ethyl N-t-butoxycarbonylaminooxoacetate (0.318 g, 1.46 mmol), and PPh3 (0.384 g, 1.46 mmol) in THF (20 mL) was added a solution of DIAD (0.32 g, 1.58 mmol) in THF (5 mL). The resulting mixture was stirred at room temperature overnight, and concentrated in vacuo. The residue was purified on flash column chromatography (silica gel, 2% EtOAc/hexane) to provide the desired product (0.535 g, 81%). 1H NMR (CDCl3, 300 MHz) delta 1.04 (s, 9H), 1.34 (t, J=6.9 Hz, 3H), 1.46 (s, 9H), 4.22-4.38 (m, 6H), 5.42 (dt, J=19.5, 7.2 Hz, 1H), 7.33-7.52 (m, 6H), 7.61-7.75 (m, 4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 60℃; | Example 49a; CBz-Protected Ethyl Alcohol Mitsunobu (11a-b); A two-necked 100 mL round bottom flask was equipped with a water-jacketed condenser, flame dried, and placed under argon atmosphere. Triphenylphosphine (0.070 g, 0.26 mmol) and N-Boc-ethyl-oxamate (0.059 g, 0.26 mmol) were added, followed by a solution of the Cbz-protected ethyl alcohol (8) (0.10 g, 0.24 mmol) in dry THF (5 mL). The solution was cooled to 0 C., and diisopropyl azodicarboxylate (0.053 mL, 0.26 mmol) was added dropwise. The reaction was then heated to 60 C., and allowed to stir overnight. The resulting light yellow liquid was concentrated in vacuo, and purified by flash chromatography (hexane-ethyl acetate 5:1) to afford a clear, colorless oil (0.050 g, 31%). This procedure is one representative sample of this reaction. This procedure was repeated for both isomers. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20℃; for 50h; | To a 3-necked round bottom flask cooled in an ice-water bath was added a solution of Ph3P (0.015 mol) in anhydrous THF (10 mL), a solution of 3-cyclopenten- L-OL (II) (0.012 mol) in anhydrous THF (10 mL), and a solution OF N-BOC ethyl oxamate (0. 015 mol) in anhydrous THF (10 mL). DEAD (0. 015 mol) was then added dropwise to the above mixture. The reaction mixture was stirred at 0 C for 2 h, and then allowed to react at room temperature for 48 h. The solvent was removed in vacuo and the residue was dissolved in CH2C12 (30 mL), and washed with water and brine (20 mL X 3). The solvent was removed in vacuo, and the residue was purified by column chromatography (silica gel, 100% dichloromethane) to yield a mixture of product, (TERT-BUTOXYCARBONYL-CYCLOPENT-3-ENYL-AMINO)-OXO-ACETIC acid ethyl ester, and N-Boc ethyl oxamate that was used without further purification. To a stirred solution cooled in an ice-water bath of the above crude product, (TERT-BUTOXYCARBONYL-CYCLOPENT-3-ENYL-AMINO)-OXO-ACETIC acid ethyl ester, (3.80 g) in THF (35 mL) was added a solution OF LIOH (0.0765 mol) in water (35 mL). The mixture was stirred in the ice-water bath for 3 h. The organic material was extracted with CH2C12 (30 ML X 3), the organic layers were combined and washed with brine (30 ML X 2), and the solvent was removed in vacuo. The residue was purified by column chromatography (silica gel, 100 % dichloromethane) to obtain white crystals of pure product (53 %). | |
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20℃; for 50h; | Example 31Synthesis of cyclopent-3-enyl-carbamic acid tert-bulyl ester (IV-I) To a 3-necked round bottom flask cooled in an ice-water bath was added a solution of Ph3P (0.015 mol) in anhydrous THF (10 mL), a solution of 3-cyclopenten- 1 -ol (II) (0.012 mol) in anhydrous THF (10 mL), and a solution of N-Boc ethyl oxamate (0.015 mol) in anhydrous THF (10 mL). DEAD (0.015 mol) was then added dropwise to the above mixture. The reaction mixture was stirred at 0 C for 2 h, and then allowed to react at room temperature for 48 h. The solvent was removed in vacuo and the residue was dissolved in CH2CI2 (30 mL), and washed with water and brine (20 mL x 3). The solvent was removed in vacuo, and the residue was purified by column chromatography (silica gel, 100% dichloromethane) to yield a mixture of product, (tert-butoxycarbonyl-cyclopent-,3-enyl-amino)-oxo-acetic acid ethyl ester, and N-Boc ethyl oxamate that was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 15℃; for 3h; | A solution of 1 -benzyl 2-methyl (2S, 4S)-4-hydroxypyrrolidine-1 ,2- dicarboxylate (2.0 g, 7.2 mmoL), triphenylphosphine (2.8 g, 10.7 mmol), lambda/-Boc-ethyl oxamate (2.3 g, 10.7 mmol) in THF (20 ml_) was cooled to 0-100C. To the stirred solution was charged DIAD (2.2 g, 10.7 mmol) while maintaining the reaction temperature 0-100C. The reaction was stirred at 0-150C for 3 h. [0214] A solution of lithium hydroxide monohydrate (0.9 g, 21.5 mmol) in water(100 ml_) was charged while maintaining the reaction temperature 0-10C. The reaction was stirred at 0-100C for 1 h. The reaction was diluted with water (10 ml_) and ethyl acetate (30 ml_). The phases were separated. The organic phase was extracted with water (15 ml_) and brine (15 ml_). <n="73"/>[0215] The ethyl acetate solution was concentrated under vacuum and the resulting residue was dissolved in toluene (20 ml_). To the stirred solution was charged methanol (6 ml_) and acetyl chloride (1 ml_). The mixture was stirred at room temperature for 16 h. The reaction mixture is diluted with 0.5 N HCI (30 ml_). The phases were separated. The toluene phase was extracted with 0.5 N HCI (15 ml_). The combined aqueous phase was extracted with EtOAc (3 x 30 ml_). [0216] The above aqueous solution was cooled to 0-10C and was basified with10 N NaOH to pH 11. The aqueous solution was extracted with EtOAc (3 x 30 mL). The combined aqueous phase was dried over MgSO4 and concentrated under vacuum to afford the title compound as a yellow oil, 0.5 g (25% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 60℃; | Example 50c; Tribenzyl Mitsunobu Product (17a-b); A two-necked 100 mL round bottom flask was equipped with a water-jacketed condenser, flame dried, and placed under argon atmosphere. Triphenylphosphine (0.16 g, 0.62 mmol) and N-Boc-ethyl-oxamate (0.14 g, 0.62 mmol) were added, followed by a solution of the tribenzyl alcohol (16) (0.39 g, 0.56 mmol) in dry THF (10 mL). The solution was cooled to 0 C., and diisopropyl azodicarboxylate (0.12 mL, 0.62 mmol) was added dropwise. The reaction was then heated to 60 C., and allowed to stir overnight. The resulting light yellow liquid was concentrated in vacuo, and purified by flash chromatography (hexane-ethyl acetate 7:1) to afford a clear, colorless oil (0.24 g, 48%). This procedure is one representative sample of this reaction. This procedure was repeated for both isomers. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diisopropyl (E)-azodicarboxylate; triphenylphosphine; In tetrahydrofuran; ethyl acetate; | To a cold (0 C.) solution of methyl 6-hydroxynorbornane-2-carboxylate, 72e, (3.2 g, 18 8 mmol) in THF (150 mL) was added <strong>[216959-34-1]ethyl 2-(tert-butoxycarbonylamino)-2-oxo-acetate</strong> (4.9 g, 22.6 mmol) and triphenylphosphine (5.9 g, 22.6 mmol) followed by dropwise addition of diisopropyl azodicarboxylate (4.5 g, 22.6 mmol). The reaction was then heated to 85 C. and maintained at that temperature for 2 days. The solvent was evaporated under reduced pressure and the crude product was purified by silica gel chromatography (0-100% EtOAc/hexanes gradient) to provide 6 g of methyl 6-(N-(tert-butoxycarbonyl)-2-ethoxy-2-oxoacetamido)bicyclo[2.2.1]heptane-2-carboxylate: LCMS 392.34 (M+Na+); 1H NMR (300 MHz, CDCl3) delta 4.26 (q, J=7.2 Hz, 2H), 4.08 (dt, J=14.3, 7.2 Hz, 1H), 3.62 (d, J=2.1 Hz, 3H), 2.72 (s, 1H), 2.42-2.26 (m, 2H), 2.08-1.80 (m, 2H), 1.80-1.51 (m, 3H), 1.45 (s, 9H), 1.38-1.25 (m, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.44 g | A mixture of Intermediate 29d (0.48 g, 2.1 mmol), ethyl 2-[(tert-butoxy)carbonyl]amino}- 2-oxoacetate (0.45 g, 2.1 mmol) and triphenylphosphine (0.60 g, 2.3 mmol) in anhydrous THF (10 mL) was stirred at -10C followed by the slow addition of DEAD (0.33 mL, 2.1 mmol). The mixture was allowed to warm to ambient temperature and stirred for 3 hrs. The reaction mixture was poured onto brine (20 mL) and extracted with diethyl ether and the combined organics were concentrated in vacuo. The residue was dissolved in THF (10 mL) and then 1 M LiOH solution (0.26 mL, 25 mmol) was added and the mixture was stirred at ambient temperature for 2 hrs. The reaction mixture was poured onto water (50 mL) and extracted with diethyl ether. The combined organic phases were concentrated in vacuo. The crude product was purified by chromatography on the Biotage Isolera Four (25 g column, 1 to 40% EtOAc in heptane) to afford title compound as an oil (0.44 g). LCMS (Method G): 0.92 min, 308 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.15 g | To a solution of Intermediate 30b (0.29 g, 0.98 mmol), ethyl 2-[(tert- butoxy)carbonyl]amino}-2-oxoacetate (0.20 mL, 0.98 mmol) and triphenylphosphine (0.28 g, 1.1 mmol) in anhydrous THF (12 mL) at -10C was slowly added DIAD (0.19 mL, 0.98 mmol). The mixture was stirred at ambient temperature for 3 hrs and then DIAD (0.39 mL, 2.0 mmol) and triphenylphosphine (0.56 g, 2.1 mmol) were added and stirring was continued for 16 hrs. Additional portions of DIAD (0.39 mL, 2.0 mmol) and triphenylphosphine (0.56 g, 2.1 mmol) were added and stirring was continued for a further 3 hrs. The mixture was then poured onto brine (12 mL) and extracted with diethyl ether. The combined organics were concentrated in vacuo. The residue was re-dissolved in THF (6 mL) and 1 M LiOH (12 mL, 0.28 mmol) was added and the mixture was stirred at ambient temperature for 16 hrs. The reaction mixture was poured onto water (30 mL) and extracted with diethyl ether. The combined organics were concentrated in vacuo. The crude product was purified by chromatography on the Biotage Isolera Four (10 g column, 0 to 100% ethyl acetate in heptane) to afford the title compound as an oil (0.15) 1H NMR (500 MHz, CDCI3) 8.25 (d, 0.43 H), 8.21 (d, 0.57 H), 7.90 (s, 0.86 H), 7.84 (s, 1.14 H), 7.30 (m, 1 H), 7.04 (bs, 0.57 H), 5.53 (bs, 0.43 H), 4.03 (m, 0.43 H), 3.66 (m, 0.43 H), 3.44 (m, 1 H), 3.32 (m, 0.57 H), 3.19 (m, 0.57 H), 3.1 1 (s, 1 .71 H), 2.87 (s, 1.29 H), 2.63 (m, 3 H), 1 .48 (s, 3.87 H), 1 .38 (s, 5.13 H), 1 (m, 1 .00 H), 0.68 (m, 1 H), 0.60 (m, 1.43 H), 0.49 (m, 1 H), 0.18 (m, 0.57 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6 mg | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 85℃; for 48h; | Formation of methyl 6-(N-(tert-butoxycarbonyl)-2-ethoxy-2-oxoacetamido)bicycle[2.2.1]heptane-2-carboxylate (72f) (2594) To a cold (0 C.) solution of methyl 6-hydroxynorbornane-2-carboxylate, 72e, (3.2 g, 18.8 mmol) in THF (150 mL) was added <strong>[216959-34-1]ethyl 2-(tert-butoxycarbonylamino)-2-oxo-acetate</strong> (4.9 g, 22.6 mmol) and triphenylphosphine (5.9 g, 22.6 mmol) followed by dropwise addition of diisopropyl azodicarboxylate (4.5 g, 22.6 mmol). The reaction was then heated to 85 C. and maintained at that temperature for 2 days. The solvent was evaporated under reduced pressure and the crude product was purified by silica gel chromatography (0-100% EtOAc/hexanes gradient) to provide 6 g of methyl 6-(N-(tert-butoxycarbonyl)-2-ethoxy-2-oxoacetamido)bicyclo[2.2.1]heptane-2-carboxylate: LCMS 392.34 (M+Na+); 1H NMR (300 MHz, CDCl3) delta 4.26 (q, J=7.2 Hz, 2H), 4.08 (dt, J=14.3, 7.2 Hz, 1H), 3.62 (d, J=2.1 Hz, 3H), 2.72 (s, 1H), 2.42-2.26 (m, 2H), 2.08-1.80 (m, 2H), 1.80-1.51 (m, 3H), 1.45 (s, 9H), 1.38-1.25 (m, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6 g | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 85℃; for 48h; | To a cold (0 C.) solution of methyl 6-hydroxynorbornane-2-carboxylate, 72e, (3.2 g, 18.8 mmol) in THF (150 mL) was added <strong>[216959-34-1]ethyl 2-(tert-butoxycarbonylamino)-2-oxo-acetate</strong> (4.9 g, 22.6 mmol) and triphenylphosphine (5.9 g, 22.6 mmol) followed by dropwise addition of diisopropyl azodicarboxylate (4.5 g, 22.6 mmol). The reaction was then heated to 85 C. and maintained at that temperature for 2 days. The solvent was evaporated under reduced pressure and the crude product was purified by silica gel chromatography (0-100% EtOAc/hexanes gradient) to provide 6 g of methyl 6-(N-(tert-butoxycarbonyl)-2-ethoxy-2-oxoacetamido)bicyclo[2.2.1]heptane-2-carboxylate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Triphenylphosphine (5.29 g, 20.2 mmol), 1-(pyridin-3-yl)pent-4-en-1-ol (3.15 g, 19.3 mmol) and ethyl2-[(tert-butoxy)carbonyl]amino}-2-oxoacetate 121 (4.40 g, 20.2 mmol) were stirred in THF (200 mL)at 0 C. DIAD (4.08 g, 20.2 mL) was added and the reaction mixture was allowed to warm up to rt andwas stirred for 16 h. The reaction mixture was concentrated in vacuo to volume and LiOH (3.0 g in20 mL H2O) was added. The reaction mixture was stirred for 1 h. The reaction was concentrated invacuo to volume again and extracted with EtOAc (3 × 100 mL), dried (Na2SO4) and concentrated invacuo. Column chromatography eluting with hexanes-EtOAc (50:50) gave the product as acolourless oil that solidified on standing (3.98 g, 78%).IR numax 3328, 3005, 2979, 2933, 2414, 1705, 1641, 1524, 1452, 1429, 1391, 1366, 1275, 1261, 1171cm-1;1H-NMR (CDCl3, 500 MHz): 8.55 (1H, s, py 2-H), 8.51 (1H, dd, J 4.8, 1.6, py 6-H), 7.58 (1H, dt, J 7.9,1.9, py 4-H), 7.26 (1H, dd, J 7.9, 4.8, py 5-H), 5.79 (1H, ddt, J 16.9, 10.3, 6.6, 4-H), 5.03 (1H, dd, J 10.3,1.6, 5-HA), 5.01 (1H, d, J 16.9, 5-HB), 4.85 (1H, br s, NH), 4.67 (1H, br s, 1-H), 2.16-1.99 (2H, m, 3-H2),1.90-1.79 (2H, m, 2-H2), 1.41 (9H, s, Boc);13C-NMR (CDCl3, 125 MHz): 155.1, 148.7, 148.3, 137.0, 133.9, 123.5, 115.8, 55.2 (from HMQC), 35.7,30.2, 28.3;HRMS (ESI+): Calculated for C15H23N2O2 ([M+H]+): 263.1754. Found: 263.1763, Delta +3.4 ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.57 g | A mixture of Int 8 (0.61 g, 3.1 mmol), ethyl 2-[(ie f-butoxy)carbonyl]amino}-2-oxoacetate (630 muIota, 3.1 mmol) and triphenylphosphine (0.88 g, 3.4 mmol) in anhydrous THF (20 mL) was cooled to -10C and treated with DEAD (0.48 mL, 3.1 mmol) by dropwise addition. The mixture was stirred at ambient temperature overnight. The solvent was removed in vacuo. The residue was poured onto brine / water (1 :1 , 20 mL) and extracted with diethyl ether. The combined organic phases were concentrated in vacuo. The residue was dissolved in THF (10 mL), LiOH (0.32 g, 13 mmol) and water (10 mL) were added and the mixture was stirred at ambient temperature for 2 hrs. The solvent was removed in vacuo. The residue was poured onto water (50 mL) and extracted with diethyl ether. The combined organic phases were concentrated in vacuo. The crude product was purified by chromatography on the Biotage Isolera Four (25 g column, 0 to 100% EtOAc in heptane) to afford title compound as a colourless oil (0.57 g). LCMS (Method B): 1 .88 min, 279 [M+H]+ 1 H NMR (500 MHz, CDC ) delta 7.31 (d, 4H), 7.26 - 7.22 (m, 1 H), 3.62 (d, 1 H), 3.43 (d, 1 H), 3.27 - 3.17 (m, 1 H), 3.01 - 2.93 (m, 1 H), 2.89-2.80 (m, 1 H), 2.13 (s, 3H), 1 .45 (s, 9H), 0.97 (d, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20℃; for 16h; | A solution ofDEAD (2.39 g, 13.74 mmol) in THF (18 ml) was added dropwise to asolution of 3-vinylpentane-1,5-diol (h, 1.05 g, 8.07 mmol), ethyl2-((tertbutoxycarbonyl)amino)-2-oxoacetate (4.41 g, 20.3 mmol), and triphenylphosphine (5.33 g,20.3 mmol) dissolved in THF (30 ml) at 0C. After completion, the reaction was warmed uptoRT and stirred for 16 hours. The solvent was removed under vacuo, the resulting residue dissolved in 50 ml ofTHF, and 10 ml of 4M LiOH (aq.) solution was added slowly at 0 C. After complete addition, the reaction was warmed up toRT and stirred for 16 hours. Solventwas removed under vacuo, and the residue was dissolved in 150 ml EtOAc and 100 ml water.The organic layer was separated, and the aqueous solution was extracted with EtOAc (1 00 mlx 2). The organic layers were combined and dried with sodium sulfate. After removing solvent, the residue was purified by column chromatography (80g, silica gel column, 0-40%EtOAc/hexane) to provide di-tert-butyl (3-vinylpentane-1,5-diyl)dicarbamate U) (1.30 g, 49%yield). 1H NMR (499 MHz, Chloroform-d) 8 5.54 (ddd, J = 17.0, 10.3, 8.9 Hz, 1H), 5.08-4.99 (m, 2H), 4.53 (s, 2H), 3.15 (s, 2H), 3.05 (s, 2H), 2.08 (qt, J = 9.2, 4.7 Hz, 1H), 1.62-1.53 (m, 4H), 1.44 (s, 18H); MS: mass calculated for C17H32N204: 328.24; found: positive: 329.5 (M+Ht, 351.4 (M+Nat. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65.01% | With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at -10 - 20℃; for 15h; | Compound II-2 (50.01 g, 0.347 mol, 1.0 eq) was dissolved in THF (500 mL). Compound III (90.47 g, 0.416 mol, 1.2 eq), triphenylphosphine (162.1 g, 0.416 mol, 1.2 eq) The temperature was lowered to -10 C, DEAD (72.56 g, 0.416 mol, 1.2 eq) was added dropwise, and the reaction was stirred at room temperature for 15 h. The reaction solution was poured into water, extracted with EA, and washed with a saturated aqueous solution of sodium hydrogencarbonate. After drying, the reaction mixture was concentrated, and the precipitated solid was removed by crystallization with PE/EA. The reaction mixture was concentrated to give compound IV-2 as a yellow liquid, 77.38 g.The yield was 65.01%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.32% | With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20℃; for 4h; | Compound II-3 (20 g, 0.139 mol, 1.0 e.q.) was dissolved in 200 mL of THF.Add compound III (45.22 g, 0.208 mol, 1.5 eq), triphenylphosphine (54.64 g, 0.208 mol, 1.5 eq), cool to 0 C, add DEAD (36.27 g, 0.208 mol, 1.5 eq) dropwise. The reaction was stirred at room temperature for 4 h, and TLC detection showed the reaction was completed. The reaction solution was poured into water, extracted with EA, washed with a saturated aqueous solution of sodium hydrogencarbonate, dried and concentrated.The compound IV-3 was concentrated to a yellow liquid of 43.04 g.The yield was 90.32%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50.05% | With tributylphosphine; di-isopropyl azodicarboxylate; In tetrahydrofuran; at 0 - 20℃; for 12h; | Compound II-4 (50.01 g, 0.347 mol, 1.0 e.q.) Dissolved in THF (600 mL), and added compound III (226.16 g, 1.042 mol, 3.0 e.q.). Tri-n-butylphosphine (210.74g, 1.042mol, 3.0e.q.), Cool down to 0 C, DIAD (210.6g, 1.041mol, 3.0e.q.) was added dropwise. Stir the reaction at room temperature for 12 h, TLC detection showed complete reaction of the starting material. The concentrated reaction liquid was subjected to sand column chromatography to obtain Compound IV-4 as a yellow liquid, 59.53 g, yield 50.05%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.05% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 12h; | Compound II-5 (50.01 g, 0.266 mol, 1.0 eq) was dissolved in THF (600 mL). Compound III (115.52 g, 0.532 mol, 2.0 eq), triphenylphosphine (139.55 g, 0.532 mol, 2.0 eq) The temperature was lowered to 0 C, DIAD (107.58 g, 0.532 mol, 2.0 eq) was added dropwise, and the reaction was stirred at room temperature for 12 h. The reaction solution was poured into water, extracted with EA, washed with a saturated aqueous solution of sodium hydrogencarbonate, dried and concentrated.The concentrated reaction liquid was subjected to sand column chromatography to obtain Compound IV-5 as a yellow liquid, 92.73 g, yield 90.05%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.03% | With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 30℃; for 4h; | Compound II-6 (50.01 g, 0.346 mol, 1.0 eq) was dissolved in 500 mL of THF. Compound III (187.8 g, 0.864 mol, 2.5 eq), triphenylphosphine (226.8 g, 0.864 mol, 2.5 eq) was added and cooled. To 0 C, DEAD (150.5 g, 0.864 mol, 2.5 eq) was added dropwise, and the reaction was stirred at 30 C for 4 h, and TLC detection showed the reaction was completed. The reaction solution was poured into water, extracted with EA, washed with a saturated aqueous solution of sodium hydrogencarbonate, dried and concentrated.The compound IV-6 was concentrated to a yellow liquid of 89.07 g.The yield was 75.03%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60.01% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at -20 - 20℃; for 12h; | Compound II-1 (50.01 g, 0.347 mol, 1.0 e.q.) was dissolved in THF (500 mL), and compound III (75.39 g, 0.347 mol, 1.0 e.q.) was added.Triphenylphosphine (135.1 g, 0.347 mol, 1.0 e.q.), cooled to -20 ° C, DIAD (70.21 g, 0.347 mol, 1.0 e.q.) was added dropwise, and the reaction was stirred at room temperature for 12 h.The reaction solution was poured into water, extracted with EA and washed with saturated aqueous sodium hydrogen carbonate.After drying, the reaction solution was concentrated, and the precipitated solid was removed by crystallization with PE/EA. The reaction solution was concentrated to give Compound IV-1 as a yellow liquid, 71.43 g. The yield was 60.01percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | Stage #1: 1-trifluoromethylprop-1-en-3-ol; ethyl 2-[(tert-butoxy)carbonyl]amino}-2-oxoacetate With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: With lithium hydroxide In tetrahydrofuran; water at 20℃; Inert atmosphere; regioselective reaction; |
Tags: 216959-34-1 synthesis path| 216959-34-1 SDS| 216959-34-1 COA| 216959-34-1 purity| 216959-34-1 application| 216959-34-1 NMR| 216959-34-1 COA| 216959-34-1 structure
[ 14719-37-0 ]
ethyl 2-((tert-Butoxycarbonyl)amino)acetate
Similarity: 0.81
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
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 |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
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 |
H411 | Toxic to aquatic life with long-lasting effects |
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 |
Sorry,this product has been discontinued.
Home
* Country/Region
* Quantity Required :
* Cat. No.:
* CAS No :
* Product Name :
* Additional Information :