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[ CAS No. 30100-16-4 ] {[proInfo.proName]}

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Chemical Structure| 30100-16-4
Chemical Structure| 30100-16-4
Structure of 30100-16-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 30100-16-4 ]

CAS No. :30100-16-4 MDL No. :MFCD00270350
Formula : C13H25NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :FPRZYWCRQHFPSX-UHFFFAOYSA-N
M.W :259.34 Pubchem ID :546215
Synonyms :

Calculated chemistry of [ 30100-16-4 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.85
Num. rotatable bonds : 11
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 70.89
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) : -6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.81
Log Po/w (XLOGP3) : 2.58
Log Po/w (WLOGP) : 2.94
Log Po/w (MLOGP) : 1.97
Log Po/w (SILICOS-IT) : 2.09
Consensus Log Po/w : 2.48

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.35
Solubility : 1.17 mg/ml ; 0.00449 mol/l
Class : Soluble
Log S (Ali) : -3.82
Solubility : 0.0396 mg/ml ; 0.000153 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.04
Solubility : 0.235 mg/ml ; 0.000908 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.41

Safety of [ 30100-16-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 30100-16-4 ]

* 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 [ 30100-16-4 ]
  • Downstream synthetic route of [ 30100-16-4 ]

[ 30100-16-4 ] Synthesis Path-Upstream   1~9

  • 1
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YieldReaction ConditionsOperation in experiment
93% With triethylamine In water; acetone at 20℃; General procedure: Di-tert-butyl dicarbonate ((Boc)2O, 11.0 mmol) in a solution of CH3COCH3(5 ml) was added dropwise to a stirred solution of amino acid (3a–6a, 10.0 mmol) andtriethylamine (Et3N, 20.0 mmol) in acetone-water (v:v 1:1, 20 ml), and the resulting solutionwas stirred for 4–8 h at room temperature until absence of amino acid (checked by TLC).The organic component of the solvent was removed under vacuum and the aqueous residuewas acidified with dilute HCl until pH 4–5. The solution was extracted with EtOAc, and thecombined organic fractions were washed with brine, dried over anhydrous Na2SO4, andthen concentrated in vacuo and freeze-dried in −80 °C to yield 3b–6b.
73% With triethylamine In methanol at 60℃; for 12 h; NH2-(CH2)7-COOH (5.00 g, 31.4 mmol), (BOC)2O (7.52 g, 34.5 mmol) and triethylamine (3.48 g, 34.5 mmol) were dissolved in 200 mL of methanol, and the mixture was stirred at 60° C. for 12 hours.
After the reaction completed, methanol was removed under reduced pressure, and the obtained material was redissolved in 100 mL of ethyl acetate.
Then, the resultant solution was subjected to separation using 0.2 mol/l HCl (twice) and water (twice), and dehydrating was carried out with anhydrous sodium sulfate.
After that, recrystallization with hexane at 4° C. and collection using a glass filter (G6) were performed, thereby obtaining Boc-NH-(CH2)7-COOH (5.93 g, 22.9 mmol, yield: 73percent).
67% With sodium hydroxide In 1,4-dioxane; water STEP 1
8-(N-tert-butyloxycarbonyl)aminooctanoic acid
8-aminooctanoic acid (10 g; 62.9 mmoles) and di-tert-butyl dicarbonate (15.1 g; 69.2 mmoles) were suspended in dioxane (20 ml) and water (4 ml).
Sodium hydroxide (1N) was added dropwise until the pH of the mixture reached 8, whereupon the solids dissolved.
After stirring overnight, the solution was neutralized with 1N hydrochloric acid.
The volume of the mixture was reduced by one half and the concentrated solution was placed in a refrigerator overnight.
The solid was filtered, washed with a minimum of cold water and air dried to yield 11 g of product (67percent yield). FAB-MS: MH+ =260.
Reference: [1] Journal of Asian Natural Products Research, 2017, vol. 19, # 3, p. 272 - 298
[2] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 4, p. 402 - 407
[3] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 12, p. 1964 - 1972
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 2, p. 718 - 738
[5] Journal of Medicinal Chemistry, 2001, vol. 44, # 26, p. 4696 - 4703
[6] Tetrahedron Letters, 1995, vol. 36, # 50, p. 9113 - 9116
[7] Patent: US8338643, 2012, B2, . Location in patent: Page/Page column 33
[8] Patent: US5614539, 1997, A,
[9] Macromolecules, 2014, vol. 47, # 23, p. 8429 - 8436
[10] Journal of the American Chemical Society, 2016, vol. 138, # 21, p. 6852 - 6860
[11] Chemical Communications, 2006, # 20, p. 2173 - 2175
[12] Patent: US2004/204389, 2004, A1, . Location in patent: Page/Page column 6-7
[13] Patent: US5877202, 1999, A,
[14] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2012, vol. 67, # 7, p. 731 - 746
[15] Molecules, 2017, vol. 22, # 4,
[16] Patent: CN107674110, 2018, A, . Location in patent: Paragraph 0038-0041
[17] Bioconjugate Chemistry, 2018, vol. 29, # 4, p. 1454 - 1465
[18] Patent: US2017/1948, 2017, A1, . Location in patent: Paragraph 0410; 0412; 0413
[19] European Journal of Medicinal Chemistry, 2019, p. 122 - 131
  • 2
  • [ 24424-99-5 ]
  • [ 30100-16-4 ]
YieldReaction ConditionsOperation in experiment
78% With sodium carbonate In 1,4-dioxane; water at 30 - 65℃; Reflux General procedure: 2.3.1 Synthesis of tert-butyloxycarbonyl- (Boc-) protected alkanoic acids (3) as shown in Scheme 6 below. Following modified literature procedures (Orwig, et al., J. Med. Chem. 2009, 52, 1803; Amara, et al., Journal of the American Chemical Society 2009, 131, 10610), bromo-terminated alkanoic acid (1, 3.62 mmol) was either dissolved (la) or suspended (lb-c) in concentrated ammonium hydroxide (10-100 mL) and stirred for 24-48 h. Upon complete consumption of starting material (monitored by thin layer chromatography, 75:25 hexanes/ethyl acetate with acetic acid), the reaction mixture was concentrated in vacuo to isolate an amine-terminated alkanoic acid intermediate (2). The intermediate was then suspended in a 1 :1 mixture of dioxane and 10percent sodium carbonate (14 mL each) and gently warmed to 30 °C. If necessary, additional water (5 mL) was added to improve stirring. Di-tert-butyl dicarbonate (3.98 mmol) was added and the reaction stirred under reflux temperatures (65 °C) overnight. The reaction mixture was concentrated in vacuo and the resulting crude mixture reconstituted in 1 N HC1 and diethyl ether and subsequently extracted with diethyl ether (4 x 80 mL). The combined organic layers were washed with 1 : 1 brine/water (80 mL total), dried over magnesium sulfate (MgS04), and the product (3) isolated in vacuo.
Reference: [1] Patent: WO2015/195563, 2015, A1, . Location in patent: Page/Page column 29; 30; 36
  • 3
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Reference: [1] Patent: WO2005/85159, 2005, A1, . Location in patent: Page/Page column 19
  • 4
  • [ 24424-99-5 ]
  • [ 74018-60-3 ]
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Reference: [1] Patent: US6084112, 2000, A,
  • 5
  • [ 1002-57-9 ]
  • [ 41840-28-2 ]
  • [ 30100-16-4 ]
Reference: [1] Carbohydrate Research, 1989, vol. 194, # C, p. 199 - 208
[2] Chemical and pharmaceutical bulletin, 2003, vol. 51, # 8, p. 899 - 903
  • 6
  • [ 1070-19-5 ]
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Reference: [1] Journal of medicinal chemistry, 1970, vol. 13, # 4, p. 744 - 745
  • 7
  • [ 935-30-8 ]
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Reference: [1] Synthetic Communications, 1996, vol. 26, # 14, p. 2641 - 2649
  • 8
  • [ 17696-11-6 ]
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Reference: [1] Patent: WO2015/195563, 2015, A1,
  • 9
  • [ 24424-99-5 ]
  • [ 74018-60-3 ]
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Reference: [1] Synthetic Communications, 1996, vol. 26, # 14, p. 2641 - 2649
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