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Product Details of [ 98303-20-9 ]

CAS No. :98303-20-9 MDL No. :MFCD01862877
Formula : C11H19NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :JQAOHGMPAAWWQO-UHFFFAOYSA-N
M.W : 229.27 Pubchem ID :581831
Synonyms :

Calculated chemistry of [ 98303-20-9 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.82
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 63.17
TPSA : 66.84 Ų

Pharmacokinetics

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) : -6.41 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.6
Log Po/w (XLOGP3) : 1.82
Log Po/w (WLOGP) : 1.48
Log Po/w (MLOGP) : 1.03
Log Po/w (SILICOS-IT) : 0.5
Consensus Log Po/w : 1.29

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.14
Solubility : 1.65 mg/ml ; 0.00718 mol/l
Class : Soluble
Log S (Ali) : -2.84
Solubility : 0.329 mg/ml ; 0.00143 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.66
Solubility : 50.7 mg/ml ; 0.221 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.73

Safety of [ 98303-20-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 98303-20-9 ]

* 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 [ 98303-20-9 ]
  • Downstream synthetic route of [ 98303-20-9 ]

[ 98303-20-9 ] Synthesis Path-Upstream   1~26

  • 1
  • [ 98303-20-9 ]
  • [ 20845-34-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 23, p. 4334 - 4343
[2] Patent: US5571832, 1996, A,
  • 2
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  • [ 15883-20-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 1998, vol. 33, # 1, p. 23 - 31
  • 3
  • [ 24424-99-5 ]
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  • [ 98303-20-9 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With potassium carbonate In water; acetone at 20℃;
Stage #2: With hydrogenchloride In water; acetone
A solution of DL-pipecolinic acid (13 g, 100 mmol), potassium carbonate (55.2 g, 400 mmol), di-tert-butyl dicarbonate (28. 4 g, 130 mmol) in acetone (30 mL) and water (100 mL) was stirred at room temperature overnight. The reaction mixture was brought to [PH-] 3 using hydrochloric acid (1 N aqueous) and then extracted with ethyl acetate (350 mL). The organic phase was separated, sequentially washed with water (200 mL) and brine (200 mL), dried (sodium sulfate), filtered and concentrated in vacuo. The isolated solid was triturated with hexanes to yield 22.7 g (99percent) of the title compound as a white [SOLID. LH-] NMR [(CDC13),] [8] [(PPM)] : 9.3 (bs, 1H), 4.84 (bd, 1H), 3.94 (m, 1H), 2.93 (m, 1H), 2.22 (m, 1H), 1.67 (m, 3H), 1.45 (m, [11H).]
70%
Stage #1: With triethylamine In 1,4-dioxane; water for 0.166667 h;
Stage #2: at 20℃; for 24 h;
To a suspension of pipecolinic acid (1.0 mmol) in dioxane:water (4.5:1.5 mL) , Et3N (1.0 mmol) was added and the resulting mixture was stirred for 10 min. Then, a solution of (BOC)2O (1.10 mmol) in 1 mL of dioxane was added dropwise and the mixture was stirred at room temperature for 24 h. The solvent was evaporated under reduced pressure, and the residue was dissolved in EtOAc (30 mL). The solution was washed with 5percent HCl (15 mL), and brine (3 x 15 mL). After the last washing procedure the pH of the aqueous layer has to be >5. The organic phase was dried over MgSO4, filtered and concentrated in vacuum. The product, 1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid (white solid, 70percent yield)2 was used to the next step without further purification.
57% With hydrogenchloride; sodium hydrogencarbonate In water EXAMPLE 9
1-(tertButoxycarbonyl)-2-piperidinecarboxylic acid
A mixture of pipecolinic acid (48.43 g, 375 mmol), di-tertbutyl dicarbonate (98.2 g, 450 mmol, 1.2 eq) and NaHCO3 (126 g, 1500 mmol, 4.0 eq) in water (1000 mL) was stirred overnight at rt.
Crushed ice (200 g) was added to the reaction mixture which was then treated dropwise with a solution of 120 mL of 12M HCl made up to 500 mL with water.
The pH was adjusted to ca.
3.5 by addition of a further amount of HCl.
The solution was extracted with EtOAc (2*500 mL) and the combined organic extract was back washed with water (2*500 mL) and evaporated in vacuo to give the product (48.7 g, 57percent) as a beige crystalline solid: mp 123°-124° C.; 1 H-NMR (CDCl3) dd;4.93 (58percent), 4.78 (42percent) (m, 1H), 3.96 (m, 1H), 2.96 (m, 1H), 2.22 (m, 1H), 1.68 (complex m, 3H), 1.23-1.50 (m, 2H), 1.46 (s, 9H); CIMS (MH+
calcd for C&11
H19 NO4): 230.
Found (MH+): 230; Anal. (calcd for C11 H19 NO4): C,H,N.
73.0% With triethylamine In 1,4-dioxane; water Piperidine-1,2-dicarboxylic acid 1-tert-butyl ester (1).
To a solution of 10.0 g (77.42 mmol) of piperidine-2-carboxylic acid in H2O/Dioxane (2OOmL, 1:1) was added 18.59g (85.16 mmol) of di-tert-butyl dicarbonate followed by 8.62g (85.16 mmol) of triethylamine, and the mixture was stirred for 16 hrs at ambient temperature.
The solution was evaporated to remove excess dioxane, diluted with H2O (100 mL) and extracted with CH2Cl2 (2*200 mL).
The organic phase was dried (MgSO4) and the evaporated to give a yellow oil which was subjected to column chromatography (CHCl3/MeOH/AcOH, 9:.8:.2) to yield 12.9g (73.0percent) of 1 as a yellow oil. TLC Rf=0.7 (CHCl3/MeOH/AcOH, 9:.8:.2)
73.0% With triethylamine In 1,4-dioxane; water Piperidine-1,2-dicarboxylic acid 1-tert-butyl ester (1).
To a solution of 10.0 g (77.42 mmol) of piperidine-2-carboxylic acid in H2O/Dioxane (200 mL, 1:1) was added 18.59 g (85.16 mmol) of di-tert-butyl dicarbonate followed by 8.62 g (85.16 mmol) of triethyl amine, and the mixture was stirred for 16 hrs at ambient temperature.
The solution was evaporated to remove excess dioxane, diluted with H2O (100 mL) and extracted with CH2Cl2 (2*200 mL).
The organic phase was dried (MgSO4) and the evaporated to give a yellow oil which was subject to column chromatography (CHCl3/MeOH/AcOH, 9:0.8:0.2) to yield 12.9 g (73.0percent) of 1 as a yellow oil. TLC Rf=0.7 (CHCl3/MeOH/AcOH, 9:0.8:0.2)

Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 20, p. 3441 - 3444
[2] Patent: WO2004/14902, 2004, A2, . Location in patent: Page 45
[3] Organic Letters, 2013, vol. 15, # 4, p. 824 - 827
[4] Journal of Organic Chemistry, 2005, vol. 70, # 15, p. 5954 - 5963
[5] Journal of Organic Chemistry, 1999, vol. 64, # 6, p. 1993 - 2002
[6] Journal of Organic Chemistry, 2002, vol. 67, # 13, p. 4414 - 4422
[7] Journal of Medicinal Chemistry, 2009, vol. 52, # 21, p. 6672 - 6684
[8] Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 738 - 741
[9] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 20, p. 5547 - 5554
[10] Journal of Medicinal Chemistry, 1992, vol. 35, # 23, p. 4334 - 4343
[11] Patent: US5571832, 1996, A,
[12] European Journal of Organic Chemistry, 1998, # 6, p. 1143 - 1153
[13] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 15, p. 4013 - 4017
[14] Patent: US2002/42377, 2002, A1,
[15] Patent: US2002/52410, 2002, A1,
[16] Patent: EP1593681, 2005, A1, . Location in patent: Page/Page column 43
[17] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 6, p. 1832 - 1837
[18] Chemical Communications, 2017, vol. 53, # 74, p. 10299 - 10302
  • 4
  • [ 157634-00-9 ]
  • [ 98303-20-9 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 16, p. 4164 - 4167
  • 5
  • [ 58632-95-4 ]
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Reference: [1] European Journal of Medicinal Chemistry, 1998, vol. 33, # 1, p. 23 - 31
[2] European Journal of Pharmaceutical Sciences, 2003, vol. 20, # 1, p. 17 - 26
  • 6
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  • [ 4043-87-2 ]
  • [ 98303-20-9 ]
Reference: [1] Patent: US4576749, 1986, A,
  • 7
  • [ 74651-77-7 ]
  • [ 4043-87-2 ]
  • [ 98303-20-9 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 1998, vol. 46, # 2, p. 616 - 619
  • 8
  • [ 675-20-7 ]
  • [ 98303-20-9 ]
Reference: [1] Organic letters, 2000, vol. 2, # 2, p. 155 - 158
  • 9
  • [ 620-08-6 ]
  • [ 98303-20-9 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 738 - 741
  • 10
  • [ 1122-96-9 ]
  • [ 98303-20-9 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 738 - 741
  • 11
  • [ 636-80-6 ]
  • [ 98303-20-9 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 738 - 741
  • 12
  • [ 123811-74-5 ]
  • [ 98303-20-9 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 738 - 741
  • 13
  • [ 36057-44-0 ]
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Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 738 - 741
  • 14
  • [ 259133-67-0 ]
  • [ 98303-20-9 ]
Reference: [1] Organic letters, 2000, vol. 2, # 2, p. 155 - 158
  • 15
  • [ 85275-45-2 ]
  • [ 98303-20-9 ]
Reference: [1] Organic letters, 2000, vol. 2, # 2, p. 155 - 158
  • 16
  • [ 131667-57-7 ]
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Reference: [1] Organic letters, 2000, vol. 2, # 2, p. 155 - 158
  • 17
  • [ 86953-81-3 ]
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Reference: [1] Organic letters, 2000, vol. 2, # 2, p. 155 - 158
  • 18
  • [ 85908-96-9 ]
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Reference: [1] Organic letters, 2000, vol. 2, # 2, p. 155 - 158
  • 19
  • [ 1070-19-5 ]
  • [ 4043-87-2 ]
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Reference: [1] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 5, p. 629 - 631
  • 20
  • [ 24424-99-5 ]
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Reference: [1] Journal of the Chemical Society, Chemical Communications, 1994, # 7, p. 879 - 880
  • 21
  • [ 1071174-39-4 ]
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Reference: [1] Journal of the Chemical Society, Chemical Communications, 1994, # 7, p. 879 - 880
  • 22
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  • [ 157634-02-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 19, p. 4861 - 4866
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 15, p. 4013 - 4017
[3] Tetrahedron Letters, 1996, vol. 37, # 13, p. 2165 - 2168
  • 23
  • [ 98303-20-9 ]
  • [ 172876-96-9 ]
  • [ 153749-89-4 ]
Reference: [1] Chemical Science, 2017, vol. 8, # 3, p. 1790 - 1800
[2] Chimia, 2017, vol. 71, # 4, p. 226 - 230
  • 24
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Reference: [1] Synthetic Communications, 2007, vol. 37, # 21, p. 3793 - 3799
[2] Patent: WO2004/14902, 2004, A2,
  • 25
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  • [ 157634-00-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 19, p. 4861 - 4866
[2] Tetrahedron Letters, 1996, vol. 37, # 13, p. 2165 - 2168
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 9, p. 2851 - 2854
[4] Journal of Organic Chemistry, 2010, vol. 75, # 20, p. 6793 - 6805
  • 26
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  • [ 18107-18-1 ]
  • [ 200184-53-8 ]
  • [ 164456-75-1 ]
Reference: [1] Journal of the American Chemical Society, 2010, vol. 132, # 21, p. 7260 - 7261
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