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CAS No. : | 63088-78-8 | MDL No. : | MFCD19217172 |
Formula : | C6H11NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RKEYKDXXZCICFZ-WHFBIAKZSA-N |
M.W : | 145.16 | Pubchem ID : | 11040828 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.83 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 38.49 |
TPSA : | 69.56 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -9.18 cm/s |
Log Po/w (iLOGP) : | 0.89 |
Log Po/w (XLOGP3) : | -2.81 |
Log Po/w (WLOGP) : | -1.2 |
Log Po/w (MLOGP) : | -3.07 |
Log Po/w (SILICOS-IT) : | -0.44 |
Consensus Log Po/w : | -1.32 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 1.1 |
Solubility : | 1810.0 mg/ml ; 12.5 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 1.9 |
Solubility : | 11600.0 mg/ml ; 80.2 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | 0.36 |
Solubility : | 336.0 mg/ml ; 2.32 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.31 |
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 palladium 10% on activated carbon; hydrogen; In ethanol; water; under 760.051 Torr; for 11.5h; | To a flask, 18.0 g (64.5 mmol) of the (2S,5S)-N-benzyloxycarbonyl-5-hydroxy-2-piperidinecarboxylic acid obtainedin , 90 mL of ethanol, and 2.5 g of 10% palladium carbon (manufactured by N. E. Chemcat Corporation,PE-type, 55.3%, containing water) were added, and hydrogenation was carried out under normal temperature andpressure. Three hours later, 22 mL of water was added thereto, and hydrogenation was carried out under normaltemperature and pressure. Disappearance of the starting material could be confirmed 8.5 hours later. The palladiumcarbon was removed by filtration, and 100 mL of water was sprinkled thereon for washing. From the obtained filtrate,the solvent was removed under reduced pressure at 45C to 55C, to obtain 11.6 g of a white slurry. The obtained slurry was analyzed by HPLC under the conditions of . As a result, the slurry was foundto contain 5-hydroxy-2-piperidinecarboxylic acid with a purity of 65 wt% in an amount of 64.5 mmol and yield of 81%.The isomer ratio was as follows: (2S,5S)-5-hydroxy-2-piperidinecarboxylic acid:(2S,5R)-5-hydroxy-2-piperidinecarboxylic acid=98.8:1.2. The material used in had a purity of as low as (2S,5S):(2S,5R)=53.7:46.3 (molar ratio), andthe purity was increased to (2S,5S):(2S,5R)=98.8:1.2 (molar ratio) by the method of the present invention. | |
263.8 mg | With palladium on activated charcoal; hydrogen; In methanol; water; at 55 - 61℃; for 8h; | ZOPA (502.6 mg) obtained in Production Example 2 was dissolved in a mixed solvent of methanol (7.5 mL) and water (7.5 mL), and palladium carbon Pd - C (Pd content: 5.06 %, Water: 58.4%) (147.3 mg) was added and the mixture was stirred at a hydrogen pressure of 0.2 MPa and 55 C. to 61 C. for 8 hours. After completion of the reaction, the reaction solution was filtered, and the filtrate was concentrated under reduced pressure to obtain OPA. Yield was 263.8 mg. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Enzymatic reaction; | The production of a mixture of 5-R- and 5-S-hydroxy-L-pipecolic acids was carried out on the basis of a cellular suspension of the strain +75 prepared as described in Example 8. 5-R,S-hydroxy-D,L-lysine (SIGMA) is added at a final concentration of 1 M. Thin silica layer chromatography of the supernatant of the incubated suspension is carried out and it reveals two compounds present in equivalent proportions with migration (Rf1=0.14, Rf2=0.20; eluant: butanol/acetic acid/water 4/1/1) and stained by ninhydrin which are distinct from those of 5-R,S-hydroxy-D,L-lysine and L-pipecolic acid. [0166] Under the same conditions, the strain +78 described in Example 7 produces two compounds identical to those produced by the strain +75. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In water; acetone; at 23 - 30℃;pH 10 - 11; | To a reactor (R-1) equipped with an additional funnel, nitrogen inlet and agitator wascharged <strong>[63088-78-8](2S,5S)-5-hydroxypiperidine-2-carboxylic acid</strong> (77.3 wt%) (50.0 g, 344 mmol), and water(150 mL). Agitation was begun, the pH adjusted to 10-11 by addition of 10 N NaOH (~ 46.5 mL)and the reactor charged with acetone (50.0 mL).In a separate reactor (R-2) equipped with an agitator and nitrogen inlet was charged 2-nitrobenzene-1-sulfonyl chloride (97%) (106.0 g, 478 mmol) and acetone (80 mL). The contentsofR-2 were transferred to R-1 at 23-30 oc while the pH of the solution was maintained at 10-11 bysimultaneously addition of 10 N NaOH. After 15 to 30 min, the pH was adjusted to about 6 byaddition of 12 N HCl. The solution was charged with EtOAc (500 mL) and the pH adjusted to 3.0by addition of 12 N HCl. The layers were separated and the aqueous back-extracted with EtOAc (150 mL X 2). To a separate reactor (R-3) was charged product lain the combined organic layers,2-nitrobenzene-1-sulfonyl chloride (73.0 g, 329 mmol), and triethylamine (130 mL). The batch inR-3 was agitated at 20-28C for 30 min. The solution was charged with water (100 mL), the layers separated, and the aqueous back extracted with EtOAc (150 mL x 2). The combined EtOAc layer was washed with 10% NaHC03 (100 mL) and brine (100 mL). The organic phase was concentrated to 150 mL upon which a crystalline slurry was formed. The concentrated solution was agitated at13-18C for 2-3 hours followed by filtration of crystalline solids. The resulting wet cake was washed with EtOAc (60 mL) and then dried under vacuum oven at 25-30C to afford 2 (65.6 g, 79% yield) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; for 3h;Reflux; | Step 1 Hydrochloride of (2S,5S)-methyl 5-hydroxypiperidine-2-carboxylate (8) [0651] To 2M hydrogen chloride - methanol (12.8 L) was added commercially available <strong>[63088-78-8](2S,5S)-5-hydroxypiperidine-2-carboxylic acid</strong> (content 84%, net 912.22 g, washed with 2M hydrogen chloride - methanol 3.1 L), followed by refluxing for 3 hours (internal temperature 63 - 67C). After the reaction solution was cooled, 1,4-dioxane (12.8 L) was added and the solvent was distilled off under reduced pressure. To the residue (4.1 kg) were added ethyl acetate (18.3 L) and ice-cooled 44% potassium carbonate aqueous solution (23.7 L), followed by layer separation of the organic layer. The aqueous layer was further extracted with ethyl acetate (3 x 18.3 L). A 50% potassium carbonate aqueous solution (7.3 L) was separated at each organic layer, the organic layers were combined, dried over anhydrous potassium carbonate (2.37 kg) and filtered, and the solvent was distilled off under reduced pressure. The residue was dissolved in toluene (9.1 L), and activated carbon (9.2 g) was added, followed by stirring for 30 minutes and filtering, and the solvent was distilled off under reduced pressure. The residue was substituted with ethyl acetate (9.1 L) and concentrated to afford 1130 g of the title compound as a pale yellow oil (content 78.9%, net 891.57 g, yield 89%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30%; 44% | With D-glucose; nicotinamide adenine dinucleotide phosphate; sodium hydroxide; In water; at 30℃;pH 8;Enzymatic reaction; | To a 1-L jar fermenter (manufactured by ABLE Corporation, type BMJ), 45 g of 5-hydroxylysine hydrochloride(230 mmol, prepared according to a method described in Bull. Chem. Soc. Jpn., 1962, 35, 2006), 2.27 mL of AdekanolLG-109, and 67.34 g (374 mmol) of glucose were added, and dissolved in water. Thereafter, 20 wt% aqueous sodium hydroxide solution was added dropwise thereto until the pH became 8. To the resulting liquid, bovine-liver-derived catalase (manufactured by Wako Pure Chemical Industries, Ltd.) was added at 2000 U/L; NADP+ (manufactured byOriental Yeast Co., Ltd.) was added at 0.2 mmol/L; and wet cells of the recombinant E. coli JM109/pKW32 (dpkA, aip,gdh, kr) prepared in Reference Example 1 were added at 25 g/L; followed by adding water to the resulting mixture to aliquid volume of 566 mL. The reaction was allowed to proceed at 30C, a stirring rate of 500 rpm, and an aeration rateof about 1 L/min for 43 hours. During the reaction, the pH was kept at 8 by adding 20 wt% aqueous sodium hydroxide solution dropwise. Exactly the same operations were carried out twice thereafter, and the reaction mixtures obtained bythe 3 rounds of operations (using 135 g of 5-hydroxylysine hydrochloride, 690 mmol) were combined. The pH of thereaction mixture was adjusted to 2.5 using 6 mol/L sulfuric acid. Thereafter, 20 wt% aqueous sodium hydroxide solution was added dropwise to adjust the pH to 4, and the resulting liquid was centrifuged at 10,000 rpm for 20 minutes to remove insoluble impurities. The obtained supernatant was passed through a microfiltration membrane (manufacturedby Asahi Kasei Corporation), and then through an ultrafiltration membrane (manufactured by Asahi Kasei Corporation), to remove impurities. Analysis of 5-hydroxy-2-piperidinecarboxylic acid contained in the resulting solution was carried out by HPLC under the conditions of . As a result, the amount of (2S,5S)-5-hydroxy-2-piperidinecarboxylic acid produced was 43.9g (302 mmol; yield, 44%), and the amount of (2S,5R)-5-hydroxy-2-piperidinecarboxylic acidproduced was 29.7g (205 mmol; yield, 30%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89 mg | With palladium 10% on activated carbon; hydrogen; In methanol; under 760.051 Torr; for 3h; | To a flask, 0.17 g of the (2S,5S)-N-benzyloxycarbonyl-5-hydroxy-2-piperidinecarboxylic acid obtained in (purity, 70 wt%; 0.41 mmol; (2S,5S):(2S,5R)=7:1 (molar ratio)), 1 mL of methanol, and 22 mg of 10% palladium carbon(manufactured by N. E. Chemcat Corporation, PE-type, 55.3%, containing water) were added, and hydrogenation wascarried out under normal temperature and pressure for 3 hours. The palladium carbon was removed by filtration through Celite, and washing with methanol-water was carried. The obtained filtrate was concentrated to obtain 89 mg of (2S,5S)-5-hydroxy-2-piperidinecarboxylic acid as a pale yellow oily substance. |
Tags: 63088-78-8 synthesis path| 63088-78-8 SDS| 63088-78-8 COA| 63088-78-8 purity| 63088-78-8 application| 63088-78-8 NMR| 63088-78-8 COA| 63088-78-8 structure
A222384[ 154307-84-3 ]
(2S,5S)-5-Hydroxypiperidine-2-carboxylic acid hydrochloride
Reason: Free-salt
A616759[ 448964-01-0 ]
(2R,5R)-5-Hydroxypiperidine-2-carboxylic acid
Reason: Optical isomers
[ 154307-84-3 ]
(2S,5S)-5-Hydroxypiperidine-2-carboxylic acid hydrochloride
Similarity: 0.98
[ 133696-21-6 ]
(2R,4R)-4-Hydroxypiperidine-2-carboxylic acid hydrochloride
Similarity: 0.93
[ 144913-66-6 ]
Methyl 4-hydroxypiperidine-2-carboxylate
Similarity: 0.83
[ 154307-84-3 ]
(2S,5S)-5-Hydroxypiperidine-2-carboxylic acid hydrochloride
Similarity: 0.98
[ 133696-21-6 ]
(2R,4R)-4-Hydroxypiperidine-2-carboxylic acid hydrochloride
Similarity: 0.93
[ 99571-58-1 ]
6-Methylpiperidine-2-carboxylic acid
Similarity: 0.92
[ 15862-86-9 ]
Piperidine-2-carboxylic acid hydrochloride
Similarity: 0.90
[ 2133-33-7 ]
(S)-Piperidine-2-carboxylic acid hydrochloride
Similarity: 0.90
[ 154307-84-3 ]
(2S,5S)-5-Hydroxypiperidine-2-carboxylic acid hydrochloride
Similarity: 0.98
[ 133696-21-6 ]
(2R,4R)-4-Hydroxypiperidine-2-carboxylic acid hydrochloride
Similarity: 0.93
[ 99571-58-1 ]
6-Methylpiperidine-2-carboxylic acid
Similarity: 0.92
[ 15862-86-9 ]
Piperidine-2-carboxylic acid hydrochloride
Similarity: 0.90
[ 2133-33-7 ]
(S)-Piperidine-2-carboxylic acid hydrochloride
Similarity: 0.90
[ 154307-84-3 ]
(2S,5S)-5-Hydroxypiperidine-2-carboxylic acid hydrochloride
Similarity: 0.98
[ 133696-21-6 ]
(2R,4R)-4-Hydroxypiperidine-2-carboxylic acid hydrochloride
Similarity: 0.93
[ 99571-58-1 ]
6-Methylpiperidine-2-carboxylic acid
Similarity: 0.92
[ 15862-86-9 ]
Piperidine-2-carboxylic acid hydrochloride
Similarity: 0.90
[ 2133-33-7 ]
(S)-Piperidine-2-carboxylic acid hydrochloride
Similarity: 0.90
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