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[ CAS No. 109523-13-9 ] {[proInfo.proName]}

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Chemical Structure| 109523-13-9
Chemical Structure| 109523-13-9
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Product Details of [ 109523-13-9 ]

CAS No. :109523-13-9 MDL No. :MFCD09750486
Formula : C14H23NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :POJYGQHOQQDGQZ-DCAQKATOSA-N
M.W : 269.34 Pubchem ID :2755991
Synonyms :

Calculated chemistry of [ 109523-13-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.86
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 75.48
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) : -6.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.6
Log Po/w (XLOGP3) : 2.58
Log Po/w (WLOGP) : 2.26
Log Po/w (MLOGP) : 1.85
Log Po/w (SILICOS-IT) : 0.89
Consensus Log Po/w : 2.03

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.87
Solubility : 0.362 mg/ml ; 0.00134 mol/l
Class : Soluble
Log S (Ali) : -3.63
Solubility : 0.0628 mg/ml ; 0.000233 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.02
Solubility : 25.9 mg/ml ; 0.0962 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.5

Safety of [ 109523-13-9 ]

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 [ 109523-13-9 ]

* 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 [ 109523-13-9 ]
  • Downstream synthetic route of [ 109523-13-9 ]

[ 109523-13-9 ] Synthesis Path-Upstream   1~7

  • 1
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  • [ 80875-98-5 ]
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YieldReaction ConditionsOperation in experiment
100%
Stage #1: With sodium hydroxide In tetrahydrofuran; water for 0.166667 h;
Stage #2: at 20℃; for 12 h;
L-octahydroindole-2-carboxylic acid (1.69 g, 10 mmol) was added to the reaction flask,Add 30 mL of THF and 30 mL of distilled water to stir,A 7 mL aqueous solution of NaOH (0.68 g, 17 mmol) was added dropwise to the ice bath,Plus,The reaction was stirred for 10 min.(Boc) 2O (2.84 g, 13 mmol)Rose to room temperature for 12h.TLC detection reaction is completed, diluted with water, with methyl tert-butyl ether extraction impurity removal,The water phase with citric acid PH to acidic,Ethyl acetate was extracted three times, the organic phases were combined, washed with saturated brine, dried over Na2SO4,Filtration and concentration gave 3.21 g of compound 1 in 100percent yield.
98% With triethylamine In tetrahydrofuran; water at 20℃; Triethylamine (8.25 mL, 59 mmol) was added to (S)-octahydroindole-2- carboxylic acid (10.0 g, 59 mmol) in a 1/1 volume/volume mixture of tetrahydrofuran/water (200 ML total), followed by addition of di-tert-butyl dicarbonate (14.0 g, 65 mmol). The reaction mixture was stirred overnight at room temperature, and then concentrated with no heating to remove tetrahydrofuran. The aqueous mixture was partitioned between ethyl acetate (300 mL), water (100 mL), and citric acid solution (50 ML, 10percent aqueous). The layers were separated, the organic layer washed with brine (50 mL), dried (magnesium sulfate), filtered and concentrated to an oil, which solidified on standing. The solid was slurried in hexanes and collected by filtration. 15.63 g, 98percent. MS (APCI-) 17 1/Z (percent): 268 (100). Calcd for C14H23NO4 : C, 62.43 ; H, 8.61 ; N, 5.20 Found: C, 62.33 ; H, 8.30 ; N, 5.15
97% With sodium hydroxide In 1,4-dioxane; water at 20℃; for 18 h; To a stirred solution of (2S, 3aS, 7AS)-OCTAHYDROINDOLE-2-CARBOXYLIC acid (30 g, 0.18 mol) in dioxane (180 ML) and 1 M NAOH (180 mL), was added di- TE7X-BUTYL DICARBONATE (48 G, 0. 22 mol). The reaction mixture was stirred for 18 hours at room temperature and then diluted with diethyl ether (500 mL) and water (500 mL). The resulting aqueous layer was removed and cooled to 0 °C. Methylene chloride (1 L) was added, and the mixture adjusted to pH 3 by the addition of 2 M HC1. The organic layer was removed and the aqueous phase extracted with methylene chloride (2 x 25Q ML). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to afford A colorless oil. Trituration with ether and hexanes followed by removal of the excess solvents afforded the desired (2S, 3aS, 7AS)-OCTAHYDROINDOLE-1, 2- dicarboxylic acid 1-TERT-BUTYL ester (4 6. 3 g, 97percent), as a white solid : NNM (300 MHz, DMSO-d6) 8 1.00-1. 70 (m, 7H), 1.32, 1.38 (2 s, 9H), 1.76-1. 98 (m, 2H), 2.01-2. 13 (m, 1H), 2.18-2. 33 (m, 1H), 3.59-3. 69 (m, 1H), 3. 99-4. 10 (m, 1H); MS (CI) 170 [M + H-100 (Boc)] +, 270 [M + H] +.
94% With triethylamine In dichloromethane (a)
To a solution of compound 5 in CH2Cl2 was added triethylamine and (Boc)2O.
The reaction was monitored by TLC.
After the starting materials were completely consumed, the mixture was diluted with CH2Cl2, washed sequentially with 1 N HCl and brine.
The organic layer was dried over Na2SO4, filtered, and evaporated to afford compound 6 as oil (94percent yield).
368 g
Stage #1: With sodium hydroxide In tetrahydrofuran; water at 0℃; for 0.25 h;
Stage #2: at 0 - 20℃; for 12 h;
To a stirred solution of (2R,3aS,7aS)-octahydro-lH-indole-2-carboxylic acid (250 g, 1.0 equiv) (1) in THF (3 L) and water (1.5 L) at 0 °C was added dropwise a cooled aqueous solution of 2.5 M NaOH (1 L). The reaction mixture was stirred for 15 minutes at the same temperature. Di-tert-butyl dicarbonate (1.3 equiv) was added dropwise, maintaining the temperature at 0 °C. The resulting reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was washed with MTBE (3 times). The aqueous phase was acidified with IM aqueous citric acid and extracted with ethyl acetate (3 times). The combined organic layers were dried over sodium sulfate and concentrated to dryness to afford (2R,3a,S',7a)S)-l-(tert-butoxycarbonyl)octahydro-lH- indole-2-carboxylic acid (368 g) (2).

Reference: [1] Patent: CN106083829, 2016, A, . Location in patent: Paragraph 0061; 0065; 0067; 0068
[2] Patent: WO2004/92132, 2004, A1, . Location in patent: Page 85
[3] European Journal of Organic Chemistry, 2008, # 5, p. 934 - 940
[4] Patent: WO2004/92132, 2004, A1, . Location in patent: Page 80-81
[5] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 23, p. 6684 - 6693
[6] Journal of Medicinal Chemistry, 1996, vol. 39, # 12, p. 2379 - 2391
[7] Patent: US2012/302538, 2012, A1, . Location in patent: Page/Page column 17
[8] Patent: WO2018/64585, 2018, A1, . Location in patent: Page/Page column 28; 29
  • 2
  • [ 960529-90-2 ]
  • [ 109523-13-9 ]
Reference: [1] Tetrahedron Asymmetry, 2007, vol. 18, # 19, p. 2358 - 2364
  • 3
  • [ 365973-21-3 ]
  • [ 109523-13-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 12, p. 3480 - 3485
  • 4
  • [ 24424-99-5 ]
  • [ 109523-13-9 ]
Reference: [1] Tetrahedron Asymmetry, 2007, vol. 18, # 19, p. 2358 - 2364
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 12, p. 3480 - 3485
  • 5
  • [ 16851-56-2 ]
  • [ 109523-13-9 ]
Reference: [1] Tetrahedron Asymmetry, 2007, vol. 18, # 19, p. 2358 - 2364
  • 6
  • [ 80828-13-3 ]
  • [ 109523-13-9 ]
Reference: [1] Tetrahedron Asymmetry, 2007, vol. 18, # 19, p. 2358 - 2364
  • 7
  • [ 192436-84-3 ]
  • [ 109523-13-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 12, p. 3480 - 3485
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