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[ CAS No. 1171080-45-7 ] {[proInfo.proName]}

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Chemical Structure| 1171080-45-7
Chemical Structure| 1171080-45-7
Structure of 1171080-45-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1171080-45-7 ]

CAS No. :1171080-45-7 MDL No. :MFCD29472311
Formula : C22H26N2O7 Boiling Point : -
Linear Structure Formula :- InChI Key :AMOSSTKBTVKFNW-VOMIJIAVSA-N
M.W : 430.45 Pubchem ID :70673933
Synonyms :

Calculated chemistry of [ 1171080-45-7 ]

Physicochemical Properties

Num. heavy atoms : 31
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.32
Num. rotatable bonds : 9
Num. H-bond acceptors : 9.0
Num. H-bond donors : 4.0
Molar Refractivity : 114.59
TPSA : 134.19 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -10.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.57
Log Po/w (XLOGP3) : -1.9
Log Po/w (WLOGP) : 1.04
Log Po/w (MLOGP) : 1.18
Log Po/w (SILICOS-IT) : 2.75
Consensus Log Po/w : 1.13

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.0
Solubility : 42.6 mg/ml ; 0.099 mol/l
Class : Very soluble
Log S (Ali) : -0.4
Solubility : 172.0 mg/ml ; 0.4 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -6.15
Solubility : 0.000304 mg/ml ; 0.000000706 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.24

Safety of [ 1171080-45-7 ]

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:

Application In Synthesis of [ 1171080-45-7 ]

* 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.

  • Upstream synthesis route of [ 1171080-45-7 ]
  • Downstream synthetic route of [ 1171080-45-7 ]

[ 1171080-45-7 ] Synthesis Path-Upstream   1~10

  • 1
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YieldReaction ConditionsOperation in experiment
94%
Stage #1: at 0℃; for 1 h;
Stage #2: at 35℃;
Example 1fEthyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate (1:1) was prepared as described below.A slurry of benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate (1:1) (100 g, 232 mmol) in ethanol (2000 ml) was cooled to 0° C. A solution of sodium ethoxide in ethanol (216 ml, 580 mmol, 21 wt percent solution) was added slowly and the mixture was stirred for 1 h at 0° C. Acetic acid (13.3 ml, 232 mmol) was added and the mixture was concentrated under vacuum below 35° C. to a final volume of 300 ml. Ethyl acetate (700 ml) was added and the mixture was concentrated to 300 ml. This procedure was repeated twice. Water (1800 ml) was added to the mixture followed by aqueous ammonia (variable) until the pH of the aqueous layer was 7.5 to 8. The layers were separated and the aqueous layer was extracted with ethyl acetate (2.x.300 ml). The combined organic layers were washed with water (500 ml) and concentrated to a final volume of 300 ml. The solution was filtered and diluted with ethyl acetate (700 ml) and warmed to 35° C. A solution of oxalic acid dihydrate (30 g, 237 mmol) in acetone (200 ml) was added and the mixture was cooled to room temperature. The solids were isolated by filtration, washed with ethyl acetate and dried under vacuum at 35° C. to obtain ethyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate (1:1) as a white solid (80.7 g, 94percent).
Reference: [1] Patent: US2012/323010, 2012, A1, . Location in patent: Page/Page column 17
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YieldReaction ConditionsOperation in experiment
69%
Stage #1: With sulfuric acid In ethyl acetate at -20 - -15℃; for 1 h;
Stage #2: With sodium tris(acetoxy)borohydride In ethyl acetate at -20 - -15℃; for 5 h;
Stage #3: at 45℃; for 2 h;
To stir,Thermometer in a 2000 ml four-necked flask500 grams of ethyl acetate,135.0 g (0.4 mole) of benzyl 5-benzyloxyiminopiperidine-2S-carboxylate (III3) are added,Maintaining negative 20°C to negative 15°C,201.0 grams of concentrated sulfuric acid (2.0 moles) was added dropwise.After dripping, stir for 1 hour.At negative 20°C,Add 190.0 g (0.9 moles) of sodium triacetoxyborohydride,The reaction was stirred at -20°C to -15°C for 5 hours.Keep the temperature below 0°C,Add 200 grams of water to quench the reaction;Ammonia is neutralized until the system has a pH of 7-8.The layers were separated and the organic layer was washed twice with 100 g each of saturated saline.The organic phase is concentrated to recover the solvent,Then, 320 g of ethyl acetate and 160 g of methanol were added to the resulting residue.52.0 g (0.42 mol) of oxalic acid dihydrate,After heating to 45°C and stirring for 2 hours,Cool, filter.The cake was washed with 100 g of a mixture of ethyl acetate/methanol (2:1) and washed with 50 g of ethyl acetate.All filtrates were combined for Example 6.The filter cake was dried under vacuum to obtain 118.8 g of the single isomer 5R-benzyloxy aminopiperidine-2S-carboxylic acid benzyl oxalate, the chiral HPLC purity was 99.7percent, and the yield was 69.0percent.
Reference: [1] Patent: CN107540600, 2018, A, . Location in patent: Paragraph 0052-0054
[2] Patent: US2012/323010, 2012, A1, . Location in patent: Page/Page column 14-15
  • 3
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YieldReaction ConditionsOperation in experiment
37.7% at 0 - 45℃; for 6 h; The benzyl (2S)-5-((benzyloxy)amino)piperidine-2-carboxylate solution (50 mL) as obtained in the previous step was heated to 45 °C, 40°C methanol (20 mL) and oxalic aicd (2.4 g, 26.7 mmol) in methanol (5 mL) solution were added, and the system was cooled to 0°C, still stood for 6 h, filtrated, and the filter cake was washed with ethyl acetate (20 mL), added to methanol (25 mL), heated to 80°C, dissolved completely, cooled to 25 °C, still stood for 2h, filtered, and the filter cake was washed with methanol (5 mL), dried to obtain the title compound in white color (4.3 g, yield 37.7 percent).
Reference: [1] Patent: EP3281942, 2018, A1, . Location in patent: Paragraph 0181; 0182
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  • [ 1401540-64-4 ]
Reference: [1] Patent: WO2014/135929, 2014, A1, . Location in patent: Page/Page column 6; 8; 9
  • 5
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YieldReaction ConditionsOperation in experiment
0.542 g at 60℃; Example 1
Production of
(2S,5R)-5-benzyloxyamino-piperidine-2-carboxylic acid benzyl ester oxalate
To the above product (0.946 g, 2.78 mmol), ethyl acetate was added to adjust the total weight at 8.63 g.
The obtained mixture was heated up to 60°C, and methanol solution (0.875 g) containing oxalic acid (0.228 g, 2.53 mmol) was added for 5 minutes.
The obtained reaction mixture was cooled down to room temperature, and the precipitate was filtrated.
The precipitate was washed with ethyl acetate (2 ml) for 3 times, and dried under reduced pressure to obtain (2S,5R)-5-benzyloxyamino-piperidine-2-carboxylic acid benzyl ester oxalate (0.903 g, 2.10 mmol, yield: 76percent).
The diastereo ratio of this solid was (2S,5R)/(2S,5S)=99.3/0.7 (98.6 percent de).
To the above solid (0.597 g), methanol (3.0 g) was added, and the obtained mixture was stirred for 1 hour at 60°C.
The reaction mixture was cooled down to room temperature, and the precipitate was filtrated.
The precipitate was washed with methanol (2 ml) for 2 times, and dried under reduced pressure to obtain (2S,5R)-5-benzyloxyamino-piperidine-2-carboxylic acid benzyl ester oxalate (0.542 g).
The diastereo ratio of this solid was (2S,5R)/(2S,5S)=99.93/0.07 (99.9 percent de).
Reference: [1] Patent: EP2650281, 2013, A1, . Location in patent: Paragraph 0071; 0072
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YieldReaction ConditionsOperation in experiment
74.5 % de for 2 h; Example 10
purification of (2S,5R)-5-benzyloxyamino-piperidine-2-carboxylic acid benzyl ester oxalate
To 5-benzyloxyamino-piperidine-2-carboxylic acid benzyl ester (0.806 g, 2.37 mmol) having diastereo ratio of (2S,5R)/(2S,5S)=77.4/22.6 (54.8 percent de), ethanol (4.75 g) and oxalic acid (0.217 g, 2.41 mmol) were added, and the obtained mixture was stirred for 2 hours.
The precipitate was filtrated, washed with ethanol (0.80 g) for 2 times, and dried at 50°C under reduced pressure to obtain 5-benzyloxyamino-piperidine-2-carboxylic acid benzyl ester oxalate (0.947g, 2.20mmol), yield: 93percent).
The diastereo ratio of this solid was (2S,5R)/(2S,5S)=87.2/12.8 (74.5 percent de).
Reference: [1] Patent: EP2650281, 2013, A1, . Location in patent: Paragraph 0081
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Reference: [1] Patent: US2012/323010, 2012, A1,
[2] Organic Process Research and Development, 2016, vol. 20, # 10, p. 1799 - 1805
[3] Patent: EP3281942, 2018, A1,
  • 8
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Reference: [1] Patent: US2012/323010, 2012, A1,
[2] Organic Process Research and Development, 2016, vol. 20, # 10, p. 1799 - 1805
[3] Patent: EP3281942, 2018, A1,
  • 9
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Reference: [1] Organic Process Research and Development, 2016, vol. 20, # 10, p. 1799 - 1805
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Reference: [1] Patent: EP3281942, 2018, A1,
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