13108-19-5|10-Aminodecanoic acid| Ambeed

CAS No. :	13108-19-5
Formula :	C₁₀H₂₁NO₂
M.W :	187.28
SMILES Code :	O=C(O)CCCCCCCCCN
MDL No. :	MFCD00270349
InChI Key :	XAUQWYHSQICPAZ-UHFFFAOYSA-N
Pubchem ID :	83150

Safety of [ 13108-19-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 13108-19-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	0
Fraction Csp3	0.9
Num. rotatable bonds	9
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	54.66
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	63.32 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.09
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	-1.57
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.15
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.7
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.85
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.24

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	0.58
Solubility	715.0 mg/ml ; 3.82 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Highly soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	0.75
Solubility	1050.0 mg/ml ; 5.6 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Highly soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.54
Solubility	0.541 mg/ml ; 0.00289 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-8.56 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<2.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.6

Application In Synthesis of [ 13108-19-5 ]

* 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.

Downstream synthetic route of [ 13108-19-5 ]

[ 13108-19-5 ] Synthesis Path-Downstream 1~54

1
[ 67-56-1 ]
[ 13108-19-5 ]
[ 106590-42-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With acetyl chloride; at 0℃; for 3h;Inert atmosphere; Reflux;	Freshly distilled acetyl chloride (1.70 mL, 23.90 mmol) was added dropwise to a stirred suspension of <strong>[13108-19-5]10-aminodecanoic acid</strong> 12 (1.80 g, 9.61 mmol) in anhydrous MeOH (20 mL) under N2 atmosphere at 0 °C. Once the addition was complete, the mixture was heated under reflux for 3 h. After completion of the reaction, the solvent and excess acetyl chloride were distilled off under reduced pressure affording the corresponding methyl 10-aminodecanoate as a white solid (89percent), which was used in the next reaction without further purification. Lithium aluminum hydride (1.65 g, 17.20 mmol) was added in small portions to a stirred suspension of the amino ester intermediate (1.73 g, 8.57 mmol) in anhydrous THF (100 mL) at 0 °C. The reaction mixture was heated under reflux for 48 h, then cooled to room temperature and poured into crushed ice. The aqueous layer was vigorously extracted with CH2Cl2 (6 x 80 mL) and the combined organic phases were washed with brine and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure and the crude product was recrystallized to obtain pure 16 (0.92 g, 62percent).

References: [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 367 - 383.
[2]Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica,1950,vol. 46,p. 727,731.

2
[ 123-99-9 ]
[ 13108-19-5 ]

References: [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1906,vol. 143,p. 362.

3
[ 1009-89-8 ]
[ 13108-19-5 ]

References: [1]Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica,1950,vol. 46,p. 727,731.

4
[ 35147-40-1 ]
[ 13108-19-5 ]

References: [1]Journal of Polymer Science,1948,vol. 3,p. 85,89.
[2]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1946,p. 68.
Chem.Abstr.,1948,p. 5849.

5
[ 99175-22-1 ]
[ 13108-19-5 ]

References: [1]Zhurnal Obshchei Khimii,1957,vol. 27,p. 2418,2422;engl.Ausg.S.2481,2484.

6
[ 37027-56-8 ]
[ 13108-19-5 ]

References: [1],1958,vol. 5,p. 53,59.
Chem.Abstr.,1961,p. 10310.

7
[ 5810-19-5 ]
[ 13108-19-5 ]

References: [1]Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry,1954,vol. 57,p. 769.
Chem.Abstr.,1955,p. 10234.
[2]Patent: US2839547,1956, .

8
[ 91017-32-2 ]
[ 13108-19-5 ]

References: [1]Patent: US2862940,1953, .
[2]Canadian Journal of Chemistry,1962,vol. 40,p. 1189 - 1195.

9
[ 105474-03-1 ]
[ 13108-19-5 ]

References: [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 2520,2522; engl. Ausg. 2556, 2558.
[2]Tetrahedron,1962,vol. 18,p. 21 - 36.

10
[ 103799-79-7 ]
[ 13108-19-5 ]

References: [1]Biochemical Journal,1937,vol. 31,p. 1376,1377.

11
[ 112-38-9 ]
[ 13108-19-5 ]

References: [1]Canadian Journal of Chemistry,1962,vol. 40,p. 1189 - 1195.
[2]Canadian Journal of Chemistry,1962,vol. 40,p. 1189 - 1195.

12
[ 108-31-6 ]
[ 13108-19-5 ]
10-((Z)-3-Carboxy-acryloylamino)-decanoic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1692 - 1703.

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 9 STR86 5R, 20S, 23S-3-(5-BENZYL-4, 7, 18, 19, 22-PENTAOXOCYCLOEICOSAHYDRO-3A, 6, 17,[21-TETRAAZACYLOPENTACYCLOHENEICOSEN-20-YL)PROPYL]GUANIDINE TRIFLUOROACETIC ACID HYDRATE COMPOUND 9 A slurry of 9-cyanopelargonic acid (8.6 g, 48 mrnol), a catalytic amount 5percentRh/Al2 O3, and 200 mL of 2.0N NH3 -EtOH was shaken under 50 psig of H2 pressure for 6 h, then filtered through dicalite. The filter pad was washed with 100 mL of hot 1:1 MeOH--H2 O, and the combined filtrates were concentrated to give 6.1 g of 10-aminodecanoic acid.

14
9-cyano-nona-3<i>t</i>,7<i>t</i>-dienoic acid methyl ester [ No CAS ]
[ 13108-19-5 ]

References: [1]Gazzetta Chimica Italiana,1959,vol. 89,p. 1390,1395.

15
oxime of/the/ κ-oxo-palmitic acid [ No CAS ]
[ 13108-19-5 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1925,p. 6.
Chemisches Zentralblatt,1926,vol. 97,p. 916.

16
convolvulinoloic acid [ No CAS ]
[ 123-99-9 ]
[ 13108-19-5 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1925,p. 4.
Chemisches Zentralblatt,1926,vol. 97,p. 915.

17
[ 103799-79-7 ]
[ 7664-93-9 ]
[ 14130-05-3 ]
[ 13108-19-5 ]
[ 1852-04-6 ]
[ 506-30-9 ]

References: [1]Biochemical Journal,1937,vol. 31,p. 1376,1377.

18
[ 75-77-4 ]
[ 13108-19-5 ]
[ 1026483-48-6 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3573 - 3576.

19
polymer; monomer(s): 4-methoxysalicylic acid [ No CAS ]
[ 13108-19-5 ]
N-(4-methoxysalicyloyl)-10-aminodecanoic acid [ No CAS ]

References: [1]Synthetic Communications,2005,vol. 35,p. 1567 - 1575.

20
poly(3,5-dichlorosalicylate) [ No CAS ]
[ 13108-19-5 ]
N-(3,5-dichlorosalicyloyl)-10-aminodecanoic acid [ No CAS ]

References: [1]Synthetic Communications,2005,vol. 35,p. 1567 - 1575.

21
[ 13108-19-5 ]
10-benzoylamino-decanoic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3573 - 3576.

22
[ 13108-19-5 ]
C₂₀H₃₃NO₃Si [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3573 - 3576.

23
[ 13108-19-5 ]
10-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-decanoic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1692 - 1703.

24
[ 1871-96-1 ]
[ 13108-19-5 ]

References: [1]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1946,p. 68.
Chem.Abstr.,1948,p. 5849.

25
[ 3930-10-7 ]
[ 13108-19-5 ]

References: [1]Zhurnal Obshchei Khimii,1957,vol. 27,p. 2418,2422;engl.Ausg.S.2481,2484.

26
[ 1561-48-4 ]
[ 13108-19-5 ]

References: [1]Zhurnal Obshchei Khimii,1957,vol. 27,p. 2418,2422;engl.Ausg.S.2481,2484.

27
[ 100131-38-2 ]
[ 13108-19-5 ]

References: [1]Zhurnal Obshchei Khimii,1957,vol. 27,p. 2418,2422;engl.Ausg.S.2481,2484.

28
[ 21010-06-0 ]
[ 13108-19-5 ]

References: [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 2520,2522; engl. Ausg. 2556, 2558.

29
[ 71877-34-4 ]
[ 13108-19-5 ]

References: [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 2520,2522; engl. Ausg. 2556, 2558.

30
[ 100132-35-2 ]
[ 13108-19-5 ]

References: [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 2520,2522; engl. Ausg. 2556, 2558.

31
[ 78845-71-3 ]
[ 13108-19-5 ]

References: [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 2520,2522; engl. Ausg. 2556, 2558.

32
[ 100370-91-0 ]
[ 13108-19-5 ]

References: [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 2520,2522; engl. Ausg. 2556, 2558.
[2]Tetrahedron,1962,vol. 18,p. 21 - 36.

33
[ 103565-56-6 ]
[ 13108-19-5 ]

References: [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 2520,2522; engl. Ausg. 2556, 2558.

34
[ 41059-02-3 ]
[ 13108-19-5 ]

References: [1]Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry,1954,vol. 57,p. 769.
Chem.Abstr.,1955,p. 10234.

35
[ 13108-19-5 ]
[ 501-53-1 ]
[ 195302-79-5 ]

Yield	Reaction Conditions	Operation in experiment
	In sodium hydroxide; water; acetonitrile;	The crude product (5.7 g) was dissolved in 15.5 mL of 2N NaOH and treated simultaneously with 23 mL of 2N NaOH and 5.8 g of carbobenzoxychloride at 0° C. with vigorous stirring over 0.5 h. Water and 2N NaOH were added as needed to maintain stirring and a pH between 10-14. After stirring for 2.5 h, the reaction was diluted with 400 mL of H2 O and filtered through dicalite. The filtrate was acidified (pH 2) with H2 SO4, then extracted with ether. The combined ether extracts were dried (Na2 SO4), filtered and concentrated. The residue was dissolved in CH3CN, filtered, and the filtrate concentrated to afford 5.3 g of 10-(N-carbobenzoxy)-aminodecanoic acid which was used without further purification: FAB-MS m/z 322 (MH+). Compound 9 was prepared using the general method of Example 1. CBZ-D-PheOH replaced CBZ-D-homophenylalanine in Step 1a and 10-(N-carbobenzoxy)-aminodecanoic acid replaced 8-carbobenzoxyaminooctanoic acid in Step 1c to give the title compound as a solid: FAB-MS m/z 598 (MH+); Anal Calc'd for C31 H47 N7 O5.1.75 C2 HF3 O2.1.75 H2 O; Calc'd: C, 50.00; H, 6.35; N, 11.83; H2 O, 3.80; Found: C, 49.62; H, 6.23; N, 11.93; H2 O, 3.46.

References: [1]Patent: US5888971,1999,A .

36
[ 23810-52-8 ]
[ 13108-19-5 ]
[ 186822-49-1 ]

References: [1]Russian Chemical Bulletin,1996,vol. 45,p. 2661 - 2662.

37
[ 13108-19-5 ]
[ 920-46-7 ]
[ 59178-93-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium carbonate; In tetrahydrofuran; water; at 0℃; for 5h;	Example 1; [0049] Synthesis of 11 -Methacrylamidoundecanoic Acid; 10-Aminodecanoic acid (4.04 g, 20 mmol) was dissolved in 300 ml of THF and water (1 :1 ) in an ice-water bath, and then sodium carbonate (3.18 g, 30 mmol) was added. Methacryloyl chloride (3.15 g, 30 mmol) was slowly added, and the mixture was <n="28"/>stirred for 5 h. After reaction was complete, the solution was neutralized to pH 5 with HCI. Then the solvent was removed by evaporation, and the residue was extracted with 200 ml CH2CI2, producing a white solid. Recrystallization from a hexane/ethyl acetate solution gave 4.96 g product (yield 92percent). Alternatively, replacing THF/H2O with CHCI3 gave a similar or higher yield.Analysis: 1HNMR (CDCI3, 400 MHz) delta: 5.69 (s, 1 H, CHH=), 5.32 (s, 1 H, CHH=), 3.30 (m, 2H, NHCH2CH2), 2.34 (t, 2H, J = 7.4 Hz, CH2CH2COOH), 1.97 (s, 3H, CH2=CHCH3), 1.48-1.70 (m, 4H, NHCH2CH2CH2 and CH2CH2CH2COOH), 1.24-1.38 (m, 12H, NHCH2CH2(CH2)6CH2CH2COOH). 13C-NMR (CDCI3, 400 MHz) delta: 179.50 (COOH), 168.86 (CH2=CCH3CONHCH2), 140.26 (CH2=CCH3CONHCH2), 119.67 (CH2=CCH3), 40.00 (CH2=CCH3CONHCH2CH2), 34.29 (CH2CH2COOH), 29.70, 29.57, 29.47, 29.40, 29.35, 29.19, 27.10, 24.90(CH2=CCH3CONHCH2(CH2)8CH2COOH), 18.92 (CH2=CCH3). ESMS (THF/H2O, negative ion): m/z = 268.2 ([M-H]", calculated: 268.2).

References: [1]Patent: WO2008/100907,2008,A2 .Location in patent: Page/Page column 26-27.

38
[ 13108-19-5 ]
[ 320-72-9 ]
N-(3,5-dichlorosalicyloyl)-10-aminodecanoic acid [ No CAS ]
C₁₉H₂₇Cl₂NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Preparation of Compound 4; [0054] Acetic anhydride (7.10 mL, 7.69 g, 75.0 mmol. 1.04 eq), <strong>[320-72-9]3,5-dichlorosalicylic acid</strong> (15.0 g, 72.5 mmol, 1.00 eq), and xylenes (40 mL) were added to a 250 mL, three-neck flask fitted with a magnetic stir bar, a thermometer, and a Dean-Stark trap with condenser. The flask was placed in a heating mantle, and heating of the cloudy white mixture begun. The reaction mixture became a clear solution around 100° C. Most of the volatile organics (xylenes and acetic acid) were distilled into the Dean-Start trap over three hours (135-146° C.). Distillation was continued for another hour (a total of 50 mL distilled), during which the pot temperature slowly rose to 165 C. and the distillate slowed to a trickle. The residue was poured off while still hot into an aluminum tray. Upon cooling a brittle yellow glass formed. The solid was ground to a fine powder. The oligo (3,5-dichlorosalicylate) produced was used without further purification. [0055] A slurry of 3.0 g of (16.0 mmol, 1.1 eq) 10-aminodecanoic acid, 9 ml (18.0 mmol, 1.13 eq) of 2 N aqueous sodium hydroxide and 30 ml of dioxane was added to a white slurry of 3.97 g (20.8 mmol, 1.3 eq) of oligo (3,5-dichlorosalicylate) and 30 ml of dioxane in a 250 mL round bottom flask equipped with a magnetic stir bar and reflux condenser. The reaction mixture was heated to 90° C. for 20 hours (at which time no further change was observed, by HPLC). The reaction mixture was cooled to 250° C. and acidified to pH=1 with 2N aqueous hydrochloric acid. The mixture was concentrated in vacuo (60 C., 50 mm). The resulting solid was recrystallized twice from ethanol-water decolorized with charcoal but was not yet clean. Column chromatography using 5:1 hexanes/ethyl acetate-1percent acetic acid as eluant gave one fraction as acid and another as ethyl ester. The ethyl ester was hydrolyzed to the acid using 4 ml of 2N aqueous sodium hydroxide and acidified with 2N aqueous hydrochloric acid. The acid was isolated by filtration. The combined acid portions were triturated with methylene chloride and hexanes to give 1.22 g of N-(3,5-dichlorosalicyloyl)-10-aminodecanoic acid.

References: [1]Patent: US2003/216589,2003,A1 .Location in patent: Page/Page column 6.

39
[ 13108-19-5 ]
[ 24424-99-5 ]
[ 173606-50-3 ]

Yield	Reaction Conditions	Operation in experiment
2.42 g	With sodium hydroxide; In water; tert-butyl alcohol; at 20℃; for 24h;	The crude product from the previous step was placed in a 100-mL round-bottom flask with a magnetic stirbar, and NaOH (505 mg, 12.6 mmol) and Boc anhydride (2.31 g, 10.6 mmol) were added. Water (11 mL) and t-butanol (5 mL) were added to the flask to dissolve the solids, and the mixture was stirred at rt for 24 h. The crude product was diluted with water (20 mL) and 1 M HCl (20 mL). The resulting mixture was extracted with ethyl acetate (30 mL, 2x) and brine (30 mL). The organic layer was isolated, dried over MgSO4, and concentrated in vacuo to yield 2.42 g of 2 as a white solid (84percent isolated yield). The 1H NMR and 13C NMR spectra for acid 2 were identical to those that were previously reported.

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 10610 - 10619.
[2]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5054 - 5057.
[3]Organic and Biomolecular Chemistry,2014,vol. 12,p. 8132 - 8137.

40
[ 50530-12-6 ]
[ 13108-19-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With ammonia; In water; at 20℃; for 24h;	10-bromodecanoic acid (2.51 gr, 10 mmol) was added to a round bottom flask containing 80 mL of aqueous ammonium hydroxide (25percent NH3). The resulting mixture was stirred for 24 hours at room temperature, after which the aqueous solution was evaporated under reduced pressure, resulting in 8b as a white solid at quantitative yield. 1H-NMR (200 MHz, CD3OD): 1.25-1.4 (m; 10H), 1.5-1.7 (m; 4H), 2.15 (t; /= 7.38 Hz; 2H), 2.89 (t; /= 7.48 Hz; 2H).
	With ammonium hydroxide; water; at 20℃; for 24h;	In a 250-mL round-bottom flask equipped with a magnetic stirbar, 10-bromodecanoic acid (2.51 g, 10.0 mmol) was dissolved in 80 mL of aqueous ammonium hydroxide (25percent NH3). The solution was stirred for 24 h at rt.Thereafter, the mixture was concentrated in vacuo to yield a white solid that was used without further purification.
1 g	With ammonium hydroxide; In water; at 20 - 45℃; for 5.25h;	A 250-mL round-bottom flask was charged with 5.0 g of 10-bromodecanoic acid from Example 2 and 100 mL of ammonium hydroxide (28percent in water). The suspension was stirred at 20 °C for 3 hours. The suspension was heated to about 45 °C for 15 minutes. The mixture was then stirred at ambient temperature for 2 hours, then filtered. The filter cake was washed with water and 50percent isopropanol. The resulting solid was dried in vacuo to give a white powder (about 1 g). The chemical shifts for the NMR were as follows (relative to TMS): 1.35 (s, 10H), 1.63-1.70 (m, 4H), 2.05-2.07 (m, 2H), 2.36-2.40 (m, 2H), 3.03-3.07 (m, 2H), 1 1.75 (approx., s, 1H).

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 10610 - 10619.
[2]Patent: WO2011/1419,2011,A1 .Location in patent: Page/Page column 19.
[3]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5054 - 5057.
[4]Organic and Biomolecular Chemistry,2014,vol. 12,p. 8132 - 8137.
[5]Patent: WO2018/80869,2018,A1 .Location in patent: Paragraph 0085.

41
[ 13108-19-5 ]
[ 1175052-30-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5054 - 5057.

42
[ 13108-19-5 ]
C₂₃H₃₇NO₈ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5054 - 5057.

43
[ 13108-19-5 ]
(S)-10,12-dioxo-12-(2-oxotetrahydrofuran-3-ylamino)dodecan-1-ammonium trifluoroacetate [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5054 - 5057.

44
[ 13108-19-5 ]
(10-amino-1-hydroxydecylidene)bisphosphonic acid [ No CAS ]

References: [1]Molecules,2012,vol. 17,p. 10928 - 10945,18.

45
[ 13108-19-5 ]
[ 50270-27-4 ]
4-chloro-2,6-bis(9-carboxynonylamino)pyrimidine-5-carbaldehyde [ No CAS ]