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[ CAS No. 17191-44-5 ] {[proInfo.proName]}

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Chemical Structure| 17191-44-5
Chemical Structure| 17191-44-5
Structure of 17191-44-5 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 17191-44-5 ]

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Product Details of [ 17191-44-5 ]

CAS No. :17191-44-5 MDL No. :MFCD02094399
Formula : C14H17NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :IXXMJXGMYKDTRQ-UHFFFAOYSA-N
M.W : 263.29 Pubchem ID :1512635
Synonyms :

Calculated chemistry of [ 17191-44-5 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.43
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 69.23
TPSA : 75.63 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) : -6.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.03
Log Po/w (XLOGP3) : 2.09
Log Po/w (WLOGP) : 2.16
Log Po/w (MLOGP) : 1.57
Log Po/w (SILICOS-IT) : 1.74
Consensus Log Po/w : 1.92

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.63
Solubility : 0.622 mg/ml ; 0.00236 mol/l
Class : Soluble
Log S (Ali) : -3.31
Solubility : 0.129 mg/ml ; 0.000492 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.3
Solubility : 0.133 mg/ml ; 0.000506 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.32

Safety of [ 17191-44-5 ]

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 [ 17191-44-5 ]

* 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 [ 17191-44-5 ]
  • Downstream synthetic route of [ 17191-44-5 ]

[ 17191-44-5 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 17191-44-5 ]
  • [ 17193-28-1 ]
Reference: [1] Journal of the Chemical Society. Perkin transactions 1, 1968, vol. 5, p. 531 - 540
  • 2
  • [ 501-53-1 ]
  • [ 52-52-8 ]
  • [ 17191-44-5 ]
YieldReaction ConditionsOperation in experiment
78%
Stage #1: With sodium carbonate In 1,4-dioxane; water at 20℃;
Stage #2: With lithium hydroxide In tetrahydrofuran; water at 20℃;
Stage #3: Acidic conditions
To a solution of 1-aminocyclopentanecarboxylic acid (3.0 g, 23.2 mmol) in 1:1 dioxane/water (60 mL), was slowly added Na2CO3 (12.3 g, 116 mmol) followed by benzyl chloroformate (3.6 mL, 25.5 mmol) and the mixture stirred overnight at RT.
The reaction mixture was carefully acidified to pH=2 with 1M HCl then extracted with EtOAc (3*30 mL).
The combined organic extracts were washed with brine (30 mL), dried (MgSO4), filtered and concentrated in vacuo to leave a pale yellow oil. LCMS and NMR showed the crude product to be a mixture of desired product and corresponding benzyl ester.
The crude product was dissolved in 1:1 THF/water (60 mL) and treated with lithium hydroxide (2.67 g, 116 mmol).
The mixture was stirred at RT overnight then washed with Et2O (3*30 mL), acidified to pH=2 and extracted with EtOAc (3*30 mL).
The combined organic extracts were washed with brine (30 mL), dried (MgSO4), filtered and concentrated under reduced pressure to afford the title compound (4.76 g, 78percent). LCMS: m/z 264 [M+H]+.
78%
Stage #1: With sodium carbonate In 1,4-dioxane; water at 20℃;
Stage #2: With hydrogenchloride In 1,4-dioxane; water
To a solution of 1-aminocyclopentanecarboxylic acid (3.0 g, 23.2 mmol) in 1 :1 dioxane / water (60 ml), was slowly added Na2CO3 (12.3 g, 116 mmol) followed by benzyl chloroformate (3.6 ml, 25.5 mmol) and the mixture stirred overnight at RT. The reaction mixture was carefully acidified to pH 2 with 1 M HCI then extracted with EtOAc (3 x 30 ml). The combined organic extracts were washed with brine (30 ml), dried (MgSO4), filtered and concentrated in vacuo to leave a pale yellow oil. LCMS and NMR showed the crude product to be a mixture of desired product and corresponding benzyl ester. The crude product was dissolved in 1 :1 THF / water (60 ml) and treated with lithium hydroxide (2.67 g, 116 mmol). The mixture was stirred at RT over night then washed with Et2O (3 x 30 ml), acidified to pH 2 and extracted with EtOAc (3 x 30 ml). The combined organic extracts were washed with brine (30 ml), dried (MgSO4), filtered and concentrated under reduced pressure to afford the title compound (4.76 g, 78percent). LCMS: m/z 264 [M+H]+.
62% With sodium carbonate In 1,4-dioxane; water at 0 - 20℃; A solution of benzyl chloroformate (0.290 g, 1.1 mmol) in dioxane (2.5 cm3) was added dropwise to a solution of 1 -aminocyclopentanecarboxylic acid (Fluka) (0.2 g, 1.54 mmol) and sodium carbonate (0.490 g, 4.64 mmol) in water (5 cm3) at 0 °C. Stirring was continued at room temperature overnight and the reaction mixture washed with ether. The aqueous layer was acidified with 2M hydrochloric acid, extracted with ethyl acetate, dried (Na2SO4), filtered and the solvent removed to afford carbamate 21 (0.253 g, 62percent) as an oil which solidified on standing. Carbamate 21 was shown to be a 70:30 mixture of conformers by 1H NMR analysis (the ratio was estimated from the integration of the resonances at δ 5.31 and 7.29-7.40, assigned to the N-H protons of the major and minor conformers, respectively): mp 70-80 °C (lit.1 82-86 °C, ethyl acetate, petroleum ether); SH (400 MHz; CDCl3; Me4Si) 1.83 (4H, br s, 2 x cyclopentyl-H2), 2.04 (2H, br s, cyclopentyl-H2), 2.20-2.40 (2H, m, cyclopentyl- H2), 5.13 (2H, br s, OCH2Ph), 5.31 (0.7η, br s, N-H) and 7.29-7.40 (5.3H, m, Ph and N-H*); δc (100 MHz; CDCl3) 24.6 (CH2, cyclopentyl-C), 37.5 (CH2, cyclopentyl-C),' denotes resonance assigned to minor conformer. <n="31"/>66.0 (quat., cyclopentyl-C), 66.8 (CH2, OCH2Ph), 128.0 (CH, Ph), 128.1 (CH, Ph), 128.4 (CH, Ph), 136.1 (quat, Ph), 155.8 (quat., NCO2) and 179.5 (quat., CO2H).
62% With sodium carbonate In 1,4-dioxane; water at 0 - 20℃; N-Benzyloxycarbonyl-1-aminocyclopentane-1-carboxylic acid 21 A solution of benzyl CHLOROFORMATE (0.290 g, 1.1 mmol) in dioxane (2.5 CM3) was added dropwise to a solution of L-AMINOCYCLOPENTANECARBOXYLIC acid (Fluka) (0.2 g, 1.54 mmol) and sodium carbonate (0.490 g, 4.64 mmol) in water (5 CM3) at 0 °C. Stirring was continued at room temperature overnight and the reaction mixture washed with ether. The aqueous layer was acidified with 2M hydrochloric acid, extracted with ethyl acetate, dried (NA2S04), filtered and the solvent removed to afford carbamate 21 (0.253 g, 62percent) as an oil which solidified on standing. Carbamate 21 was shown to be a 70: 30 mixture of conformers by 1H NMR analysis (the ratio was estimated from the integration of the resonances at No. 5.31 and 7.29-7. 40, assigned to the N-H protons of the major and minor conformers, respectively): mp 70-80 °C (lit. l 82-86 °C, ethyl acetate, petroleum ether); IH (400 MHz; CDC13 ; Me4Si) 1.83 (4H, br s, 2 x CYCLOPENTYL-H2), 2.04 (2H, br s, cyclopentyl-H2), 2.20-2. 40 (2H, M, cyclopentyl- H2), 5.13 (2H, br s, OCH2Ph), 5.31 (0.7H, br s, N-H) and 7.29-7. 40 (5.3H, M, Ph and N-H*) ; DC (100 MHz; CDC13) 24.6 (CH2, cyclopentyl-C), 37.5 (CH2, cyclopentyl-C), 66.0 (quat. , cyclopentyl-C), 66.8 (CH2, OCH2PH), 128.0 (CH, Ph), 128.1 (CH, Ph), 128.4 (CH, Ph), 136.1 (quat, Ph), 155.8 (quat. , NC02) and 179.5 (quat. , CO2H).
62% With sodium carbonate In 1,4-dioxane; water at 0 - 20℃; N-Benzyloxycarbonyl-l-aminocyclopentane-l-carboxylic acid 21 A solution of benzyl chloroformate (0.290 g, 1.1 mmol) in dioxane (2.5 cm3) was added dropwise to a solution of l-aminocyclopentanecarboxylic acid (Fluka) (0.2 g, 1.54 mmol) and sodium carbonate (0.490 g, 4.64 mmol) in water (5 cm3) at 0 °C. Stirring was continued at room temperature overnight and the reaction mixture washed with ether. The aqueous layer was acidified with 2M hydrochloric acid, extracted with ethyl acetate, dried (Na2SC>4), filtered and the solvent removed to afford carbamate 21 (0.253 g, 62percent) as an oil which solidified on standing. Carbamate 21 was shown to be a 70:30 mixture of conformers by NMR analysis (the ratio was estimated from the integration of the resonances at 6 5.31 and 7.29-7.40, assigned to the N-H protons of the major and minor conformers, respectively): mp 70-80 °C (lit.1 82-86 °C, ethyl acetate, petroleum ether); < (400 MHz; CDC; Me4Si) 1.83 (4H, br s, 2 x cyclopentyl-H2), 2.04 (2H, br s, cyclopentyl-H2), 2.20-2.40 (2H, m, cyclopenty[-H2), 5.13 (2H, br s, OCiPh), 5.31 (0.7H, br s, N-H) and 7.29-7.40 (5.3H, m, Ph and N-H*); <5fc (100 MHz; CDC13) 24.6 (CH2, cyclopentyl-C), 37.5 (CH2, cyclopentyl-C), 66.0 (quat., cyclopentyl-C), 66.8 (CH2) OCH2Ph), 128.0 (CH, Ph), 128.1 (CH, Ph), 128.4 (CH, Ph), 136.1 (quat, Ph), 155.8 (quat, NC02) and 179.5 (quat., C02H).

Reference: [1] Organic Process Research and Development, 1998, vol. 2, # 4, p. 238 - 244
[2] Patent: US2010/317865, 2010, A1, . Location in patent: Page/Page column 14; 15
[3] Patent: WO2009/106844, 2009, A1, . Location in patent: Page/Page column 39
[4] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 2001, vol. 40, # 1, p. 70 - 74
[5] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 2, p. 533 - 548
[6] Patent: WO2008/63311, 2008, A2, . Location in patent: Page/Page column 29-30
[7] Patent: WO2005/23815, 2005, A2, . Location in patent: Page/Page column 42-43
[8] Patent: WO2015/13397, 2015, A2, . Location in patent: Page/Page column 45-46
[9] Journal of the Chemical Society, 1962, p. 4601 - 4607
[10] Journal of the Chemical Society. Perkin transactions 1, 1968, vol. 5, p. 531 - 540
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