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CAS No. : | 114873-13-1 | MDL No. : | MFCD00151887 |
Formula : | C14H17Cl2NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UGZIQCCPEDCGGN-LLVKDONJSA-N |
M.W : | 334.20 | Pubchem ID : | 7015811 |
Synonyms : |
|
Num. heavy atoms : | 21 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.43 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 81.36 |
TPSA : | 75.63 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.66 cm/s |
Log Po/w (iLOGP) : | 2.51 |
Log Po/w (XLOGP3) : | 3.77 |
Log Po/w (WLOGP) : | 3.51 |
Log Po/w (MLOGP) : | 3.01 |
Log Po/w (SILICOS-IT) : | 2.97 |
Consensus Log Po/w : | 3.15 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -4.04 |
Solubility : | 0.0307 mg/ml ; 0.0000919 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.05 |
Solubility : | 0.00297 mg/ml ; 0.00000888 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.38 |
Solubility : | 0.014 mg/ml ; 0.0000418 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.83 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
With 1-hydroxy-7-aza-benzotriazole; 1,3-di-tert-butylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With acetic acid; silver(l) oxide In N,N-dimethyl-formamide at 20℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.00 g | With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 16.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: Et3N / tetrahydrofuran 2: diethyl ether 3: aq. C6H5CO2Ag / dioxane / 20 °C / sonication 4: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; HOBT; DIEA / dimethylformamide 5: CF3CO2H / CH2Cl2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran 2: diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: Et3N / tetrahydrofuran 2: diethyl ether 3: aq. C6H5CO2Ag / dioxane / 20 °C / sonication 4: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; HOBT; DIEA / dimethylformamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: DIPCDI; HOAt; DIEA / dimethylformamide 2: TFA / CH2Cl2 3: Et3N / methanol / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: DIPCDI; HOAt; DIEA / dimethylformamide 2: TFA / CH2Cl2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: DIPCDI; HOAt; DIEA / dimethylformamide 2: TFA / CH2Cl2 3: Et3N / methanol / Heating 4: NaH / dimethylformamide 5: TFA / CH2Cl2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: DIPCDI; HOAt; DIEA / dimethylformamide 2: TFA / CH2Cl2 3: Et3N / methanol / Heating 4: NaH / dimethylformamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: DIPCDI; HOAt; DIEA / dimethylformamide 2: TFA / CH2Cl2 3: Et3N / methanol / Heating 4: NaH / dimethylformamide 5: TFA / CH2Cl2 6: HATU; HOAt; DIEA / dimethylformamide 7: TFA |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: DIPCDI; HOAt; DIEA / dimethylformamide 2: TFA / CH2Cl2 3: Et3N / methanol / Heating 4: NaH / dimethylformamide 5: TFA / CH2Cl2 6: HATU; HOAt; DIEA / dimethylformamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; | 5.5-1 Example 5: Ethyl 4-cyclohexyl-1-((R)-3-(3,4-dichlorophenyl)-2-{3-[2-(1 H- imidazol-4-yl)ethyl]ureido}propionyl)piperidine-4-carboxylate:5-1 Ethyl 1-[(R)-2-tert-butoxycarbonylamino-3-(3,4-dichlorophenyl)propionyl]-4- cyclohexylpiperidine^-carboxylate0.5 g (2.1 mmol) of ethyl pipehdine-4-cyclohexyl-4'-carboxylate (cf. preparation 4-1- 2), 0.7 g (2.1 mmol) of (R)-2-tert-butoxycarbonylamino-3-(3,4-dichlorophenyl)- propionic, 0.31 g (2.3 mmol) of HOBT, 0.44 g (2.3 mmol) of EDC and 0.73 ml (4.2 mmol) of diisopropylethylamine are placed in 5 ml of DMF. The mixture is stirred for 2 hours at room temperature. The reaction is stopped by addition of an aqueous 5% citric acid solution. The organic compounds are extracted with ethyl acetate, then the organic phase is washed with aqueous 1 N sodium hydroxide solution and then with water. The organic phase is dried over sodium sulfate, filtered and concentrated. The oil obtained is chromatographed on silica gel (eluent: 1/1 heptane/ethyl acetate). 300 mg of ethyl 1 -[(R)-2-tert-butoxycarbonylamino-3-(3,4-dichlorophenyl)propionyl]-4- cyclohexylpiperidine-4-carboxylate are obtained in a yield of 26%. 1H NMR CDCh: results given in figure 4 (mixture of conformers) |
26% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; | 21.1 21-1 Ethyl 1-[(R)-2-tert-butoxycarbonylamino-3-(3, 4-dichlorophenyl)propionyl]-4- cyclohexylpiperidine-4-carboxylate; 0.5 g (2.1 mmol) of ethyl piperidine-4-cyclohexyl-4'-carboxylate (cf. preparation 3-1 - 2), 0.7 g (2.1 mmol) of Boc-3,4-dichloro-D-phenylalanine, 0.31 g (2.3 mmol) of HOBT, 0.44 g (2.3 mmol) of EDC and 0.73 ml. (4.2 mmol) of diisopropylethylamine are placed in 5 ml_ of dimethylformamide. The mixture is stirred for 2 hours at room temperature and then washed with aqueous 5% citric acid solution and extracted with ethyl acetate. The organic phase is washed with aqueous 1 N sodium hydroxide solution and then with water and dried over sodium sulfate, filtered and finally concentrated to dryness. The oil obtained is chromatographed (eluent: 5/5 heptane/ethyl acetate). 300 mg of ethyl 1 -[(R)-2-tert-butoxycarbonylamino-3-(3,4- dichlorophenyl)propionyl]-4-cyclohexylpiperidine-4-carboxylate are obtained in a yield of 26%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; lithium hydroxide In tetrahydrofuran; methanol at 0℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With dmap; 2,2'-dipyridyl carbonate In toluene at 78℃; for 10h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium hydroxide In 1,4-dioxane; water at 20℃; | 123.1 Step 1: (2R)-2-(tert-butoxycarbonylamino)-3-(3,4-dichlorophenyl)propanoic acid In a round-bottomed flask, to a stirred solution of 3,4-dichloro-D-phenylalanine (96%, 600 mg, 2.46 mmol) in 1,4-dioxane (9.8361 mL) and water (4.918 mL) at 0 °C were added successively 1 M NaOH (4.9 mL, 4.92 mmol) and di-tert-butyl dicarbonate (591 mg, 2.71 mmol) slowly. The mixture was stirred overnight at room temperature. Ethyl acetate was added, the mixture was cooled to 0 °C and acidified to pH = 3 with 1.0 M KHSO4. Layers were separated and the aqueous layer was extracted twice more with ethyl acetate. The combined organic layers were dried over Na2SO4and concentrated in vacuo to afford the title compound as a white solid (1.04 g, 100% yield, tr = 0.89 min). LCMS (Method F): m/z found 234.1 [M+H-Boc]+;1H-NMR (DMSO-d6, 400 MHz): δ (ppm) 12.65 (s, 1H), 7.60 - 7.48 (m, 2H), 7.26 (dd, J=8.3, 1.9 Hz, 1H), 7.19 - 6.70 (m, 1H), 4.12 (td, J=10.5, 4.5 Hz, 1H), 3.05 (dd, J=13.8, 4.4 Hz, 1H), 2.82 (dd, J=13.7, 10.8 Hz, 1H), 1.32 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: HATU; N-ethyl-N,N-diisopropylamine / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 10 min / 20 °C / Inert atmosphere; Sealed tube 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: HATU; N-ethyl-N,N-diisopropylamine / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 10 min / 20 °C / Inert atmosphere; Sealed tube 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 3.1: hydrogenchloride / 1,4-dioxane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: HATU; N-ethyl-N,N-diisopropylamine / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 10 min / 20 °C / Inert atmosphere; Sealed tube 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 3.1: hydrogenchloride / 1,4-dioxane / 20 °C 4.1: triethylamine / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 20 °C / Sealed tube; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | Stage #1: (R)-2-tert-butoxycarbonylamino-3-(3,4-dichlorophenyl)propionic acid With N-ethyl-N,N-diisopropylamine; HATU In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 20℃; Inert atmosphere; Sealed tube; Stage #2: dimethyl amine In tetrahydrofuran; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 20℃; | 123.2 Step 2: tert-butyl N-[(lR)-1-[(3,4-dichlorophenyl)methyl]-2-(dimethylamino)-2-oxo- ethyl] carbamate In a sealed vialunder nitrogen, to a stirred solution of (2R)-2-(tert- butoxycarbonylamino)-3-(3,4-dichlorophenyl)propanoic acid (0.82 g, 2.47 mmol) and [dimethylamino(triazolo[4,5-b]pyridin-3-yloxy)methylene]-dimethyl- ammonium;hexafluorophosphate (98%, 1245 mg, 3.21 mmol) in DCM (11.217 mL) was added N-ethyl-N-isopropyl-propan-2-amine (0.65 mL, 3.70 mmol). The reaction was stirred at rt for 10 minutes then 2 M dimethylamine in THF (3.7 mL, 7.40 mmol) was added and the suspension was stirred overnight at rt. The resulting solution was diluted with DCM and an halfsaturated solutionof NaHCO3, and the aqueous layer was extracted twice with DCM. The organic layers were dried over phase separator, concentrated in vacuo and purified by flash chromatography on silica gel using a gradient of EtOAc in Heptane from 25% to 50% to afford the title compound as a colorless oil (661 mg, 74% yield, tr = 0.91 min). LCMS (Method F): m/z found 361.3 [M+H]+;1H-NMR (DMSO-d6, 400 MHz): δ (ppm) 7.61 - 7.49 (m, 2H), 7.26 (dd, J=8.3, 2.0 Hz, 1H), 7.08 (d, J=8.8 Hz, 1H), 4.56 (td, J=9.3, 5.1 Hz, 1H), 2.97 (s, 3H), 2.87 (dd, J=13.7, 5.0 Hz, 1H), 2.82 (s, 3H), 2.75 (dd, J=13.5, 9.7 Hz, 1H), 1.29 (s, 9H). |
[ 51301-86-1 ]
2-((tert-Butoxycarbonyl)amino)-3-(4-chlorophenyl)propanoic acid
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