Structure of H-Gly-OIpr·HCl
CAS No.: 14019-62-6
*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. : | 14019-62-6 |
Formula : | C5H12ClNO2 |
M.W : | 153.61 |
SMILES Code : | O=C(OC(C)C)CN.[H]Cl |
MDL No. : | MFCD00151826 |
InChI Key : | UBKCIXXGQRZHRO-UHFFFAOYSA-N |
Pubchem ID : | 23033482 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.8 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 37.11 |
TPSA ? Topological Polar Surface Area: Calculated from |
52.32 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.81 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.7 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.39 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.22 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.34 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.1 |
Solubility | 12.1 mg/ml ; 0.0786 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.49 |
Solubility | 4.97 mg/ml ; 0.0323 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.39 |
Solubility | 63.3 mg/ml ; 0.412 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.66 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.07 |
* 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 |
---|---|---|
86% | With thionyl chloride; at 0℃;Reflux; | Glycine (lg, 13.3 mmol) was dissolved in isopropanol (10 mL) at 0C. SOCl2 (1.93 mL, 26.6 mmol) was added dropwise. The mixture was stirred at reflux overnight. After cooling, the solvent was evaporated under reduced pressure and hexane was added at 0C. The suspension was filtered to afford the product (1.76 g, 86%) as a white solid. NMR (300 MHz, MeOD) delta 5.13 (hept, J = 6.3 Hz, 1H, (CH3)2CHO), 3.81 (s, 2H, CH2), 1.32 (s, 3H, (CH3 2CHO . 1.30 (s, 3H, iCH3}2CHO). 13C NMR (75 MHz, MeOD) delta 168.0 (C), 71.7 ((CH3)2CHO), 41.2 (CH2), 21.9 ((CH3 2CHO . HRMS [M+H]+ C5H12NO2: Calcd. 1 18.0858 found 1 18.0863. |
In the 100ml three-necked flask, 30ml of isopropyl alcohol was added, and then 2.6ml of SOCl2 was added dropwise. The temperature of the dropping process was controlled at -10C to 0C, and the reaction was continued under stirring for 1 hour after the addition. 0.75g of glycine was added, and the mixture was warmed naturally to react at room temperature for 3h. The solution turned into a white emulsion, and the mixture was heated at reflux for 4 h until the solid completely disappeared. After removal of excess ethanol and SOCl2 under reduced pressure, a yellow viscous liquid was obtained. | ||
With thionyl chloride; at 0 - 20℃; for 4h; | General procedure: A solution of thionyl chloride (4.5ml, 0.06mol) in anhydrous ethanol (30ml, 0.52mol) was added to glycine (3.3g, 0.02mol) with stirring at 0C for 1h and then at room temperature for another 3h. L-ethyl glycinate hydrochloride was synthesized after removal of the solvent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With N-ethylmorpholine;; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20℃; | To a stirred solution of XI (52.6 mg, 0.20 mmole) and THF (2 ml) were added isopropyl glycinate HCl salt (30.4 mg, 0.21 mmole), EDC (40.1 mg, 0.21 mmole), HOBt (27.0 mg, 0.21 mmole) and 4-ethylmorpholine (0.03 ml, 0.21 mmole). After stirring at R.T. for overnight under N2, the solvent was removed under reduced pressure. CH2Cl2 (3 ml) was added to the residue and the insoluble solid was removed. The CH2Cl2 layer was then washed with saturated NaHCO3 solution, 1M KHSO4, saturated NaHCO3 solution and H2O. The organic layer was dried over Na2SO4, filtered and concentrated to get crude product. It was purified by column chromatography on silica gel eluting with EA: CH2Cl2 (1:20) to obtain yellow solid XII-2 (31.7 mg, 44%). 1H NMR (500 MHz, CDCl3) delta 7.94 (s, 1H), 7.71 (d, J=4.5 Hz, 1H), 7.63 (d, J=4.5 Hz, 1H), 6.73 (s, 1H), 5.12 (septet, J=6.5 Hz, 1H), 4.18 (d, J=4.5 Hz, 2H), 1.29 (d, J=6.5 Hz, 6H). HRMS Calcd for C16H13NO5S2: 363.0235, Found: 363.0226 mp=240.2240.5 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With N-ethylmorpholine;; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20℃; | To a stirred solution of XIV (244.6 mg, 0.90 mmole) and THF (8 ml) were added isopropyl glycinate HCl salt (140.0 mg, 0.92 mmole), EDC (190.0 mg, 0.99 mmole), HOBt (125.0 mg, 0.93 mmole) and 4-ethylmorpholine (0.12 ml, 0.80 mmole). After stirring at R.T. for overnight under N2, the solvent was removed under reduced pressure. CH2Cl2 (12 ml) was added to the residue and the insoluble solid was removed. The CH2Cl2 layer was then washed with saturated NaHCO3 solution, 1M KHSO4, saturated NaHCO3 solution and H2O. The organic layer was dried over Na2SO4, filtered and concentrated to get crude product. It was purified by column chromatography on silica gel eluting with EA: CH2Cl2 (1:30) to obtain yellow solid XV (75.1 mg, 21%). 1H NMR (500 MHz, CDCl3) delta 7.95 (s, 1H), 7.70 (d, J=5.0 Hz, 1H), 7.65 (d, J=5.0 Hz, 1H), 6.73 (t, J=4.5 Hz, 1H), 5.12 (septet, J=6.5 Hz, 1H), 4.18 (d, J=4.5 Hz, 2H), 1.29 (d, J=6.5 Hz, 6H). HRMS Calcd for C16H13NO5S2: 363.0235, Found: 363.0228 mp=231.8233.0 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4-methyl-morpholine; toluene-4-sulfonic acid; isobutyl chloroformate; In N,N-dimethyl-formamide; at -10 - 20℃; for 11.16h; | Example 1; Preparation of Creatinyl-Glycine Iso-Propyl Ester Acetate; Suspension of 5.67 g (38 mM) of Creatine monohydrate in 40 mL of N,N-Dimethylformamide was placed into a 250 mL 1-necked round bottom flask charged with a pressure equalization arm dropping funnel closed with calcium chloride tube then 7.23 g (38 mM) of p-Toluenesulfonic acid monohydrate was added at stirring on a magnetic stirrer. Creatine monohydrate is completely dissolved in 5 min. Then 6.71 g (40 mM) of Glycine iso-Propyl Ester Hydrochloride was added and reaction mixture was cooled down to (-)10 C. at ice-salted bath after its dissolution. Then 5.24 mL (38 mM) of iso-Butylchloroformate was added and 8.9 mL (81 mM) of N-Methylmorpholine was added via dropping funnel for 10 min. Reaction mixture was stirred at ice bath for 1 hour then a temperature was adjusted to room condition. N-Methylmorpholine hydrochloride precipitate formed was filtered off in 10 hours, a mother liquor was evaporated at 50 C. An oily residue was dissolved in 160 mL of chloroform and kept at (-)10 C. for 10 hours. Solution was filtered, extracted with H2O (3×100 mL). A combined aqueous phase containing a desired product was extracted with chloroform twice, an aqueous solution was evaporated in vacuo up to volume of 50 mL. Resulted solution was flowed through a column 30×250 mm filled with a Dowex 1×8 in acetate form in H2O. Eluent-H2O, elution rate-2 mL/min. Column was eluted with H2O monitoring a pH of eluate. Fractions with a pH=7 were collected, analysed by Reverse Phase HPLC, combined, an acetic acid was added and fractions were evaporated. A residue was crystallized with 20 mL of acetonitrile at (-)10 C. for 20 hours. A precipitate of Creatinyl-Glycine iso-Propyl Ester Acetate was filtered off, washed with chilled acetonitrile, diethyl ether and dried. A resulted product was dissolved in 30 mL of ethanol, kept at (-)10 C. for 20 hours, a solution was filtered, ethanol was removed in vacuo, a residue was crystallized with diethyl ether. Yield of Creatinyl-Glycine iso-Propyl Ester Acetate C9H18N4O3*C2H4O2: 2.3 g (21%). Mass-spectra, found: m/z 290.29. Calculated: M 290.32. Assay of Creatinyl-Glycine iso-Propyl Ester Acetate by non-aqueous titration-97.7% mass, creatinine impurity content-1.5% mass. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With potassium carbonate; In acetonitrile; at 20℃; for 48h; | To a solution of 4-(bromomethyl)-N-(4-(3-bromophenyl)thiazol-2- yl)benzamide (60 g, 0.13 mmol), K2CO3 (53 mg, 0.38 mmol) in CH3CN at 0C was added the <strong>[14019-62-6]2-isopropoxy-2-oxoethanaminium chloride</strong> (22.3 mg, 0.145 mmol). The mixture was stirred two days at room temperature. The mixture was filtered through Celite pad, washed with DCM and evaporated to dryness. Purification by silica gel flash chromatography (DCM/MeOH 95:5) afforded the product (28.5 mg, 45%) as a yellow viscous oil. NMR (300 MHz, CDCb) delta 7.88 (dd, J = 1.7, 1.7 Hz, 1H, Har), 7.80 (d, J= 8.3 Hz, 2H, Har), 7.65 (ddd, J= 7.8, 1.5, 1.1 Hz, 1H, Har), 7.37 (ddd, J = 8.0, 1.9, 1.0 Hz, 1H, Har), 7.34 (d, J = 8.2 Hz, 2H, Har), 7.19 (s, 1H, Har), 7.18 (dd, J = 7.9, 7.9 Hz, 1H, Har), 5.10 (Hept, J = 6.3 Hz, 1H, Har), 3.85 (s, 2H, CH2), 3.43 (s, 2H, CH2), 1.27 (s, 3H, (CH3 2CHO , 1.24 (s, 3H, (CH3 2CHO . 13C NMR (75 MHz, CDC13) delta 171.87 (C), 165.30 (C), 159.33 (C), 148.83 (C), 144.67 (C), 136.54 (C), 131.17 (C), 131.12 (CH), 130.47 (CH), 129.43 (CH), 128.87 (2xCH), 128.07 (2xCH), 124.82 (CH), 123.15 (C), 109.39 (CH), 69.02 ((CH3)2CHO), 52.97 (CH2), 50.57 (CH2), 22.17 ((CH3 2CHO . HRMS [M+H]+ C22H23BrN3O3S: Calcd. 488.0624 found 488.0638. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8% | General procedure: A solution of compound 2a (0.5 g, 3.47 mmol) inMeOH (10 ml) and 2O (5 ml) was treated with 33%formaldehyde solution (1.15 ml, 13.9 mmol), the respectiveamine (6.94 mmol), and 20% aqueous NaOH solution to 7-8. The reaction mixture was stirred for 24-32 h at65 under nitrogen stream. After removal of methanol bydistillation, the obtained oil was dissolved in water,acidified with hydrochloric acid to pH ~1-2, extracted withHCl3; the chloroform extracts containing the unreactedtetrahydrothiopyran-4-one 2a were discarded. The aqueoussolution was adjusted with NaOH to pH ~10 and extractedwith HCl3. The extracts were dried over anhydrousMgSO4, the solvent was removed by distillation. Thecompounds were obtained as thick oils, which wereseparated by column chromatography on neutral alumina.The eluents were composed of the following solvents: and B - EtOAc-hexane, 1:6 and 1:4; C - benzene-EtOH,10:1; D - EtOAc-petroleum ether, 1:3, 1:2, and 1:1. In thecase of compounds 6d-f, the reaction mixture after 24 hwas adjusted to 4 by adding AcOH and refluxed for8 h; the mixture 6d-f/7d-f was obtained in ratio 1:1.5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Ca. 58% | With triethylamine; In chloroform; at -10 - 20℃; for 6h; | In a 100 ml three-necked flask, the synthesized <strong>[14019-62-6]glycine isopropyl ester hydrochloride</strong> was added, followed by the addition of 10 ml of chloroform and 2 ml of triethylamine. After cooling in an ice-salt bath, the chloroform diluted chloroformylationized sorbic acid solution was added dropwise, and the temperature was controlled to -10 ~ 0 C in the dripping process. The reaction was then continued under stirring for 2h, and the reaction was warmed naturally to react at room temperature for 4h. A cloudy yellow liquid was obtained. The excess chloroform and other low boiling substances were removed under reduced pressure. Ethyl acetate and distilled water was added for extraction. The ethyl acetate extract was then added with the same amount of 0.5mol / L sodium hydroxide solution to wash 3 times. The ethyl acetate was then removed from the ethyl acetate extract under reduced pressure to get a yellow solid. The resulting yellow solid was chromatographed on a silica gel column and eluted with a 2: 1 by volume mixture of petroleum ether and ethyl acetate as the mobile phase. The eluent of the same fraction was collected and the solvent removed under reduced pressure to give a lighter yellow solid. The yield was about 58%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; at -78 - 20℃; for 1h; | 2.1 g (0.01 mol) of phenol dichlorophosphate and 1.53 g (0.01 mol) of <strong>[14019-62-6]glycine isopropyl ester hydrochloride</strong> were dissolved30 mL of anhydrous dichloromethane,Cooled to -78 C.A solution of 2 g of triethylamine in 20 mL of anhydrous dichloromethane was added dropwise with stirring,The dropping speed was controlled to maintain the reaction temperature -78 C.After the addition, the reaction temperature was gradually raised to room temperature and stirring was continued for 1 hour.The solvent was evaporated under reduced pressure, and 30 ml of anhydrous ether was added to the residue, and the mixture was filtered. The filtrate was evaporated to dryness under reduced pressure to give the title compound IV-3 as a colorless oil, which was used directly in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With triethylamine; In methanol; at 20℃; for 24h; | General procedure: The appropriate glycine ester hydrochloride (17.7 mol) and Et3N (2.2mL, 17.7 mol) were added to a solution of 2-hydroxybenzophenone (1; 3.5 g, 17.7 mmol) in MeOH (10 mL), and the solution was stirred atr.t. for 24 h. The mixture was then concentrated in vacuo and acetone was added. The precipitated Et3N·HCl was collected by filtration and washed with acetone. The filtrate was evaporated to dryness, and the product was crystallized from MeOH (for 2a,b) or from DCM-hexanes (for 2c). Important The recovered 2-hydroxybenzophenone (1) could be repeatedly used to prepare the initial product 2 (for recovery method, see below). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70.7% | With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20℃; | 6-bromo-3-hydroxypyrazine-2-carboxylic acid (5.45 g, 24.89 mmol),Glycine ethyl ester hydrochloride (4.21g,27.38 mmol) and 30 ml N,N-dimethylformamide were added to the reactor.Triethylamine (11.5 ml) and HBTU (10.5 g, 27.53 mmol) were added separately.The reaction solution was stirred overnight at room temperature, quenched with water, added with 50 ml of brine, and extracted twice with 100 ml of ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated to dryness under reduced pressure to give the target as a white solid. 5.60g, yield 70.7%, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In chloroform; at 0 - 60℃; for 7h; | General procedure: A solution of L-ethyl glycinate hydrochloride and sorbic chloride in chloroform (15ml) was added to triethylamine (2ml, 0.014mol) with stirring at 0C for 3h and then at 60C for 4h. The reaction mixture was poured into water (25ml), extracted with ethyl acetate (3×25ml), washed with NaOH solution (0.5mol/l, 2×25ml) and then dried over anhydrous MgSO4. After removal of the solvent under reduced pressure, the residual paste was purified by column chromatography (silica gel, petroleum ether/ethyl acetate, 2:1) to give Etheyl N-[1-oxo-2, 4-hexadien-1-yl] glycinate (a1). Other compounds (a2-a7 and b1-b7) were synthesized using procedures similar to that described above for compound a1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In chloroform; at 0 - 60℃; for 7h; | General procedure: A solution of L-ethyl glycinate hydrochloride and sorbic chloride in chloroform (15ml) was added to triethylamine (2ml, 0.014mol) with stirring at 0C for 3h and then at 60C for 4h. The reaction mixture was poured into water (25ml), extracted with ethyl acetate (3×25ml), washed with NaOH solution (0.5mol/l, 2×25ml) and then dried over anhydrous MgSO4. After removal of the solvent under reduced pressure, the residual paste was purified by column chromatography (silica gel, petroleum ether/ethyl acetate, 2:1) to give Etheyl N-[1-oxo-2, 4-hexadien-1-yl] glycinate (a1). Other compounds (a2-a7 and b1-b7) were synthesized using procedures similar to that described above for compound a1. |