Structure of 388109-26-0
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 388109-26-0 |
Formula : | C8H12O4 |
M.W : | 172.18 |
SMILES Code : | O=C(C1C(COCC1)=O)OCC |
MDL No. : | MFCD19440853 |
InChI Key : | APAWJCZGOJKZPB-UHFFFAOYSA-N |
Pubchem ID : | 21362493 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
With p-toluenesulfonic acid monohydrate; In benzene; | Part D. Preparation of (R)-5-(1-Phenyl-ethylamino)-3,6-dihydro-2H-pyran-4-carboxylic acid ethyl ester A solution of <strong>[388109-26-0]3-oxo-tetrahydro-pyran-4-carboxylic acid ethyl ester</strong> (3.03 g, 17.6 mmol), R-(+)-alpha-methylbenzylamine (2.35 g, 19.4 mmol) and p-toluenesulfonic acid hydrate (67 mg, 230 mumol) in benzene (60 mL) was heated at reflux under a Dean-Stark trap for 16 h. The cooled mixture was concentrated in vacuo to provide the product as a yellow oily semisolid (5.05 g), used without further purification. 1H NMR (300 mHz, CDCl3) delta 8.97 (bd, J=7.3 Hz, 1H), 7.3-7.2 (m, 5H), 4.41 (m, 1H), 4.30 (d, J=16.1 Hz, 1H), 4.18 (q, J=7.3 Hz, 2H), 3.91 (d, J=16.1 Hz, 1H), 3.64 (m, 2H), 2.34 (m, 2H), 1.48 (d, J 6.5 Hz, 3H), 1.30 (t, J 7.3 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With potassium tert-butylate; In tetrahydrofuran; toluene; | Part C. Preparation of 3-oxo-tetrahydro-pyran-4-carboxylic acid ethyl ester A solution of 4-ethoxycarbonylmethoxybutyric acid ethyl ester (90%, 15.0 g, 61.9 mmol) in toluene (300 mL) was stirred at room temperature and treated over 5 min with a solution of potassium tert-butoxide in tetrahydrofuran (1.0 M, 74.2 mL, 74.2 mmol). The mixture was stirred at room temperature for 24 h, then was poured into 1 N hydrochloric acid. The phases were separated, and the aqueous phase was extracted with ether. The combined organic phases were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (5% ethyl acetate/hexanes) to provide the product as a pale yellow liquid (5.06 g, 48%). 1H NMR (300 mHz, CDCl3) delta 11.85 (s, 1H), 4.24 (q, J=7.3 Hz, 2H), 4.14 (t, J=1.7 Hz, 2H), 3.79 (t, J=5.5 Hz, 2H), 2.35 (tt, J=5.5, 1.7 Hz, 2H), 1.32 (t, J=7.3 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluoromethylsulfonic anhydride; | Step 1: To a solution of <strong>[388109-26-0]ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate</strong> (1.0 g, 5.81 mmol) in DCM (30 mL) was added DIPEA (1.22 mL, 6.97 mmol) and Tf2O (1.08 mL, 6.39 mmol) at -78 C., then it was warmed up to room temperature and stirred at room temperature for 2 h, the solution was diluted with DCM, washed with Sat. NaHCO3, brine, dried and concentrated to give ethyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydro-2H-pyran-4-carboxylate as crude product (2 g). | |
With trifluoromethylsulfonic anhydride; | Step 1 To a solution of <strong>[388109-26-0]ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate</strong> (1.0 g, 5.81 mmol) in DCM (30 mL) was added DIPEA (1.22 mL, 6.97 mmol) and Tf2O (1.08 mL, 6.39 mmol) at -78 C., then it was warmed up to room temperature and stirred at room temeperature for 2 h, the solution was diluted with DCM, washed with Sat. NaHCO3, brine, dried and concentrated to give ethyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydro-2H-pyran-4-carboxylate as crude product (2 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 20℃; for 4.5h;Inert atmosphere; | To a solution of <strong>[388109-26-0]ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate</strong> (1.01 g, 5.58 mmol,) dissolved in DCM (28 mL) and cooled under N2 to -78C, was added DIPEA (1.2 mL, 6.9 mmol). The reaction mixture was stirred under N2, then a 1M solution of trifluoromethanesulfonic anhydride in DCM (6.07 mL, 6.07 mmol) was added. The reaction mixture was stirred at -78C for 30 minutes, then warmed to r.t. and stirred for 4 h. Saturated aqueous NaHCO3 solution (30 mL) was added. The mixture was stirred rapidly at room temperature for 5 minutes, then filtered. The organic layer was concentrated in vacuo to afford ethyl 5-(trifluoromethylsulfonyloxy)-3,6-dihydro-2H- pyran-4-carboxylate (1.7 g, quantitative) as a brown oil. |
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 20℃; for 2.0h; | Step 1 To a solution of <strong>[388109-26-0]ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate</strong> (1.0 g, 5.81 mmol) in DCM (30 mL) was added DIPEA (1.22 mL, 6.97 mmol) and Tf2O (1.08 mL, 6.39 mmol) at -78 C., then it was warmed up to room temperature and stirred at room temperature for 2 h, the solution was diluted with DCM, washed with Sat. NaHCO3, brine, dried and concentrated to give ethyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydro-2H-pyran-4-carboxylate as crude product (2g). | |
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 20℃; for 2.0h; | O1 161 Step 1: i?o a solution of eth I 3-oxotetrahvdro2i 1.p ran-4-?carhoxvlate (1 0 g, 5.8mmo )in 1X?M (30 mu was added D1PI.A 1 .22 ml., 6.97 mmcl) and FfO (1 08 ml., 6.39mmoi at 78 C. then it us warmed up to room temperature and stirred at roomtemepemature fhr 2 h, the o1ution as diluted with DCM, ashcd with Sat. aH(O, brine.dried and concentated to give eih3 I 5?1((trifluoronieth l)sulton I oxy).?3,6?dih dio-21 lp mam4-cai boxy late as crude product (2 , |
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 20℃; for 2.0h; | Step 1:To a solution of <strong>[388109-26-0]ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate</strong> (1.0 g, 5.81 mmol) in DCM (30 mL) was added DIPEA (1.22 mL, 6.97 mmol) and Tf2O (1.08 mL, 6.39 mmol) at -78 C., then it was warmed up to room temperature and stirred at room temperature for 2 h, the solution was diluted with DCM, washed with Sat. NaHCO3, brine, dried and concentrated to give ethyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydro-2H-pyran-4-carboxylate as crude product (2 g). | |
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; | To a solution of <strong>[388109-26-0]ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate</strong> (4.40 g, 25.50 mmol) and DIEA (13.21 ml, 76.66 mmol) in 120 ml of DCM at 0 C was added triflic anhydride (4.62 ml, 28.11 mmol) and the mixture was allowed to stir overnight at room temperature. DCM was removed under vacuum and the residue dissolved in EtOAc and washed with 1 N HCI and then brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluting with 20% EtOAc/heptane to yield ethyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydro-2H- pyran-4-carboxylate as a light brown oil. Mass spectrum (ESI, m/z): Calculated for C9H11F3O6S, 305.2 (M+H), Measured 305.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 20℃; for 2.0h; | Step 1 To a solution of <strong>[388109-26-0]ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate</strong> (1.0 g, 5.81 mmol) in DCM (30 mL) was added DIPEA (1.22 mL, 6.97 mmol) and Tf2O (1.08 mL, 6.39 mmol) at -78 C., then it was warmed up to room temperature and stirred at room temperature for 2 h, the solution was diluted with DCM, washed with Sat. NaHCO3, brine, dried and concentrated to give ethyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydro-2H-pyran-4-carboxylate as crude product (2 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With acetic acid; In ethanol; for 2.0h;Reflux; | To the intermediate 4 (500 mg, 1.87 mmol) in EtOH (50 mL), ethyl 3-oxotetrahydro-2H- pyran-4-carboxylate (0.55 mL, 3.74 mmol, 2 eq.) and AcOH (1.07 mL, 18.69 mmol, 10 eq.) were added. The reaction mixture was stirred at reflux for 2 hours then cooled to room temperature and evaporated under reduce pressure. The residue was triturated in DIPE. Theprecipitate was filtered to give intermediate 44 (675 mg, 100 % pure, 96 % yield).LCMS (M + 1) = 375.1H NMR (400 MHz, DMSO-d6) oe ppm 1.31 - 1.47 (m, 11 H) 1.56 (br. s., 2 H) 1.70 (d,J5.06 Hz, 1 H) 2.32 (d, J12.98 Hz, 1 H) 2.44 - 2.48 (m, 2 H) 2.70 - 2.88 (m, 1 H) 3.81 -3.96 (m, 3 H) 4.51 (s, 2 H) 5.32 (br. s., 1 H) 5.77 (s, 1 H) 12.08 (br. s., 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium carbamate; In methanol; at 25℃; for 2.0h; | A mixture of methyl 5-(3-methoxy-3-oxopropyl)tetrahydrofuran-2-carboxylate (3 g, 17.4 mmol) and H4OCO H2 (2.65 g, 34.9 mmol) in MeOH (20 mL) was stirred at 25C for 2 h. The mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluting with 5: 1 petroleum ether/ethyl acetate) to give the product. XH MR (400MHz, CD3OD) delta 4.17 - 4.03 (m, 4H), 3.73 (t, J=5.5 Hz, 2H), 2.37 - 2.19 (m, 2H), 1.24 (t, J=7.0 Hz, 3H). |