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CAS No. : | 63845-33-0 | MDL No. : | MFCD02179010 |
Formula : | C16H21NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NZTJJLCAFTZAGK-UHFFFAOYSA-N |
M.W : | 291.34 | Pubchem ID : | 9895315 |
Synonyms : |
|
Num. heavy atoms : | 21 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 82.81 |
TPSA : | 66.84 Ų |
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) : | -6.5 cm/s |
Log Po/w (iLOGP) : | 2.6 |
Log Po/w (XLOGP3) : | 2.22 |
Log Po/w (WLOGP) : | 2.37 |
Log Po/w (MLOGP) : | 2.08 |
Log Po/w (SILICOS-IT) : | 2.04 |
Consensus Log Po/w : | 2.26 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.85 |
Log S (ESOL) : | -2.79 |
Solubility : | 0.468 mg/ml ; 0.00161 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.26 |
Solubility : | 0.161 mg/ml ; 0.000551 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.16 |
Solubility : | 0.201 mg/ml ; 0.00069 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.32 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
100% | With sodium hydrogencarbonate In tetrahydrofuran; water at 0℃; for 6.41667 h; | The PIPERIDINE-HCL from Step 1 (6.5 g, 33.6 mmol) was diluted into THF (300 mL) and saturated aqueous sodium bicarbonate (100 mL), cooled to 0 °C, and treated with a solution of benzyl chloroformate (4.8 ML, 33.6 mmol) in THF (55 ML) dropwise over 25 min. The reaction mixture was maintained at 0 °C for 6 h, and then the mixture was concentrated in vacuo to remove the THF, partitioned between chloroform and 3 M HCI until gas evolution ceased at pH 2-3. The solid was filtered, the filtrate dried over anhydrous sodium sulfate and concentrated in vacuo to provide 1- (BENZYLOXYCARBONYL)-4-PIPERIDINEPROPANOIC acid (10 g, quantitative) as a pale yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With sodium hydroxide In water at 20℃; for 16 h; Cooling with ice | To prepare compound 2, a procedure published in DE 4304650 A1 was followed with modifications. 3000 mg (16.7 mmol) 2-(piperidin-4-yl) acetic acid hydrochloride (Iris Biotech, Marktredwitz, Germany) was dissolved in 46 ml of a 1 M solution of NaOH in water and cooled in an ice bath. 3350 μl benzyloxycarbonyl chloride (Cbz-Cl) (23.46 mmol, 4002 mg) were added dropwise over 5 min under stirring. The reaction mixture was allowed to warm to room temperature and stirred for 16 h. The aqueous solution was washed twice with 20 ml of diethyl ether/petroleum ether 4:1 and then acidified with 4 M HCl (aq.) to pH 1 . The product of the reaction was extracted with 3x 50 ml diisopropyl ether. The combined organic phases were dried with MgSO4 and evaporated under reduced pressure. Compound 2 was obtained as a colorless solid (4383 mg, 15.8 mmol, 95percent). 1H NMR (400 MHz, Chloroform-d) δ 7.40 - 7.27 (m, 5H), 5.13 (s, 2H), 4.18 (d, J = 13.3 Hz, 2H), 2.81 (t, J = 12.8 Hz, 2H), 2.29 (d, J = 7.0 Hz, 2H), 1.96 (tp, J = 11.2, 3.5 Hz, 1 H), 1.75 (d, J = 12.1 Hz, 2H), 1.30 - 1.09 (m, 2H). Compound 9 was synthesized as described for compound 2 in step 1 of Example 2. Starting from 1100 mg (7.00 mmol) 3-(piperidin-4-yl)propionic acid (CHESS, Mannheim, Germany), compound 9 was obtained as a colorless, highly viscous oil (1904 mg, 6.53 mmol, 93 percent). 1H NMR (400 MHz, Chlorotorm-d) δ 7.39 - 7.27 (m, 5H), 5.13 (s, 2H), 4.25 - 4.11 (m, 2H), 2.82 - 2.68 (m, 2H), 2.37 (t, J = 7.6 Hz, 2H), 1.73 - 1.64 (m, 2H), 1.60 (q, = 7.3 Hz, 2H), 1.53 - 1.37 (m, 1 H), 1.20 - 1.05 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With hydrogenchloride; potassium hydroxide In ethanol; water | (a) To a stirred and cooled (15° C.) mixture of 11.1 parts of potassium hydroxide and 96 parts of water was added dropwise a solution of 31.8 parts of ethyl 1-[(phenylmethoxy)carbonyl]-4-piperidinepropanoate in 38 parts of ethanol during 20 minutes. Upon complete addition, stirring was continued overnight at room temperature. The reaction mixture was evaporated at <50° C. The reaction mixture was poured into crushed ice and treated with concentrated hydrochloric acid. The separated aqueous layer was extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding 29 parts (100percent) of 1-[(phenylmethoxy)carbonyl]-4-piperidinepropanoic acid as a residue (int. 33). |
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