[ CAS No. 6287-90-7 ] {[proInfo.proName]}

Name: 6287-90-7|Methyl 11-bromoundecanoate|98%
Brand: Ambeed
SKU: A664529
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Quality Control of [ 6287-90-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 6287-90-7 ]

Product Details of [ 6287-90-7 ]

CAS No. :	6287-90-7	MDL No. :	MFCD00045047
Formula :	C₁₂H₂₃BrO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HFNPVFKUZYCDIB-UHFFFAOYSA-N
M.W :	279.21	Pubchem ID :	223913
Synonyms :

Calculated chemistry of [ 6287-90-7 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.92
Num. rotatable bonds :	11
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	68.95
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.27 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.44
Log Po/w (XLOGP3) :	5.26
Log Po/w (WLOGP) :	4.07
Log Po/w (MLOGP) :	3.56
Log Po/w (SILICOS-IT) :	4.26
Consensus Log Po/w :	4.12

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	1.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.16
Solubility :	0.0194 mg/ml ; 0.0000694 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.56
Solubility :	0.000766 mg/ml ; 0.00000274 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.85
Solubility :	0.00391 mg/ml ; 0.000014 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.74

Safety of [ 6287-90-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 6287-90-7 ]

* 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 [ 6287-90-7 ]
Downstream synthetic route of [ 6287-90-7 ]

[ 6287-90-7 ] Synthesis Path-Upstream 1~3

1
[ 6287-90-7 ]
[ 1611-56-9 ]

Yield	Reaction Conditions	Operation in experiment
98.9%	With hydrogenchloride In diethylene glycol dimethyl ether; water	(2) Sodium Borohydride (16.32 g, 0.43 mole) was dissolved in diglyme (350 ml). To this was added a solution of aluminium trichloride (19.2 g, 0.14 mole) in diglyme (250 ml) maintaining the temperature below 20°. After the addition was complete, the mixture was stirred for 0.5 hour at room temperature. The reducing agent was then added dropwise to a solution of methyl 11-bromoundecanoate* (120 g, 0.43 mole) in diglyme (200 ml) maintaining the temperature at 10°. After the addition was complete the reaction was stirred at 20° for 3 hours and then quenched by pouring onto water (2 L) and concentrated HCl (100 ml). The quenched mixture was stirred for 1 hour then cooled to 15°. The product was filtered off, washed with water (2500 ml) and dried under vacuum to give 11-bromoundecanol (106.8 g, 98.9percent). This methyl ester can be produced in quantitative yield by esterifying 11-bromoundecanoic acid with MeOH/H₂ SO₄

Reference： [1] Patent: US5441731, 1995, A,

2
[ 6287-90-7 ]
[ 1611-56-9 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 2, p. 455 - 461
[2] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 248 - 251[3] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 2, p. 279 - 282
[4] Tetrahedron, 2009, vol. 65, # 20, p. 3961 - 3966
[5] Journal of the American Chemical Society, 1975, vol. 97, # 9, p. 2488 - 2496

3
[ 6287-90-7 ]
[ 112-42-5 ]
[ 1611-56-9 ]

Reference： [1] Synthetic Communications, 1996, vol. 26, # 6, p. 1143 - 1147

[ 6287-90-7 ] Synthesis Path-Downstream 1~48

1
[ 67-56-1 ]
[ 2834-05-1 ]
[ 6287-90-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In methanol; for 72h;	Synthesis of methyl 11-bromoundecanoate: A mixture of 13.25 g of 11- bromoundecanoic acid, 100 mL of methanol and 10 drops of hydrochloric acid was stirred for 3 days in a closed flask. The solvent was removed in vacuo and the residual oil was redissolved in ether (100 mL). This solution was subsequently washed twice with 25 mL of a saturated NaHCO3 solution, once with water (25 mL) and once with brine (25 mL). Drying over sodium sulfate and removal of the solvents in vacuo gave 13.32 g of the product as a yellowish oil, which was sufficiently pure to use in the next step. 1H NMR (200MHz, CDCl3): delta 3.65 (s, 3H); 3.39 (t, 2H); 2.28 (t, 2H); 1.90-1.78 (m, 2H); 1.70-1.50 (m, 2H); 1.50-1.21 (m, 12H) ppm. IR (neat, cm"1): 2928 (m); 2855 (m); 1741 (s).
	With toluene-4-sulfonic acid;	A simple protocol was used for the synthesis of methyl 11-(alkylamino) undecanoate (or) secondary amine monoester (3a-c and 3g-h) as follows; initially 11-bromoundecanoic acid (1) was converted into methyl 11-bromoundecanoate (2) by reacting with methanol in presence of p-Toluenesulfonic acid (PTSA). In the second step, methyl 11-bromoundecanoate was converted into methyl 11-(alkylamino) undecanoate by reacting with different aliphatic amines) like hexyl, dodecyl, octadecyl, dioctyl and dicyclohexyl amines in presence of base catalyst K2CO3 at 90-110C for 12 h.

Reference： [1]Chemical Communications,2008,p. 4001 - 4003
[2]Tetrahedron,2009,vol. 65,p. 3961 - 3966
[3]Organic and Biomolecular Chemistry,2014,vol. 12,p. 6915 - 6921
[4]Bulletin de la Societe Chimique de France,1994,vol. 131,p. 317 - 329
[5]Organic Letters,2018,vol. 20,p. 6938 - 6942
[6]European Journal of Medicinal Chemistry,2018,vol. 148,p. 314 - 324
[7]Bulletin of the Chemical Society of Japan,1994,vol. 67,p. 455 - 461
[8]New Journal of Chemistry,2001,vol. 25,p. 1182 - 1184
[9]Journal of Molecular Liquids,2020,vol. 317
[10]Tetrahedron,1992,vol. 48,p. 5969 - 5984
[11]Macromolecules,2003,vol. 36,p. 5947 - 5959
[12]Chemical Communications,2007,p. 1322 - 1324
[13]Carbohydrate research,1984,vol. 127,p. 27 - 33
[14]Tetrahedron,1999,vol. 55,p. 13659 - 13682
[15]Synlett,2004,p. 1735 - 1738
[16]Journal of Organic Chemistry,1984,vol. 49,p. 873 - 878
[17]Tetrahedron,2006,vol. 62,p. 4838 - 4843
[18]Journal of the American Chemical Society,1959,vol. 81,p. 4335
Journal of the American Chemical Society,1959,vol. 81,p. 6275
[19]Journal of the Chemical Society,1928,p. 2680
[20]Journal of the American Chemical Society,1975,vol. 97,p. 2488 - 2496
[21]Canadian Journal of Chemistry,1962,vol. 40,p. 1846 - 1850
[22]Journal of the American Chemical Society,1971,vol. 93,p. 3738 - 3747
[23]Journal of the American Chemical Society,1999,vol. 121,p. 11425 - 11431
[24]Patent: WO2008/67436,2008,A2 .Location in patent: Page/Page column 72
[25]Journal of Organic Chemistry,2012,vol. 77,p. 9641 - 9651
[26]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1978 - 1982
[27]Medicinal Chemistry Research,2017,vol. 26,p. 1689 - 1696
[28]Medicinal Chemistry Research,2017,vol. 26,p. 2592 - 2601

2
[ 6287-90-7 ]
[ 996-82-7 ]
[ 505-52-2 ]

Reference： [1]Journal of the Chemical Society,1901,vol. 79,p. 1192

3
[ 111-81-9 ]
[ 6287-90-7 ]

Reference： [1]Synlett,2010,p. 2014 - 2018
[2]Journal fur praktische Chemie (Leipzig 1954),1960,vol. 10,p. 265 - 289
[3]Journal of Organic Chemistry,1981,vol. 46,p. 3113 - 3115
[4]Tetrahedron,1988,vol. 44,p. 2763 - 2772
[5]Chemistry of Natural Compounds,1980,vol. 16,p. 82 - 85
Khimiya Prirodnykh Soedinenii,1980,vol. 16,p. 97 - 102

4
[ 6287-90-7 ]
[ 1611-56-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1994,vol. 67,p. 455 - 461
[2]Journal of Organic Chemistry USSR (English Translation),1984,vol. 20,p. 248 - 251
Zhurnal Organicheskoi Khimii,1984,vol. 20,p. 279 - 282
[3]Tetrahedron,2009,vol. 65,p. 3961 - 3966
[4]Journal of the American Chemical Society,1975,vol. 97,p. 2488 - 2496

5
[ 6287-90-7 ]
[ 929-33-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium iodide; In acetone; at 22℃; for 19h;	To a solution of commercially available <strong>[6287-90-7]methyl 11-bromoundecanoate</strong> (5.80 g, 20.8 mmol) dissolved in dry acetone (70 mL) was added sodium iodide (4.05 g, 27.0 mmol). The reaction mixture was stirred at room temperature (22 C.) for 19 h under an inert nitrogen atmosphere. Afterwards, the acetone was evaporated and the residue transferred into an extraction funnel with diethyl ether (100 mL) and water (40 mL). The organic phase was washed with a thiosulfate solution (5% w/v, 2×20 mL) and with water 3×40 mL. The organic phase was dried, filtered on a short column of celite and celica (1 cm/4 cm) with a mixture of hexanes : acetone as the eluent. Evaporation of the solvent gave the title compound (95%) as an oil, which was used without further purification at the next step. [0231] IR (NaCl, numax, cm-1): 1731 (CO), 1200 and 1164 (C-O). [0232] 1H-NMR (200 MHz, CDCl3, delta ppm): 3.67 (3H, s, CH3), 3.19 (2H, t, J=7.0 Hz, CH2I), 2.30 (2H, t, J=7.4 Hz, RCH2COOCH3), 1.85-1.75 (2H, m, ICH2CH2R), 1.66-1.58 (2H, m, RCH2CH2COOCH3), 1.43-1.29 (12H, br s, 6×CH2). [0233] MS (m/e): 327 (M++H+), 295 (M+-OCH3). [0234] Exact mass: calculated for C11H24IO2 (M++H+)=327.0821; found=327.0813.
89%	With sodium iodide; In acetone; for 16h;Heating / reflux;	1 1-Bromo undecanoic acid methyl ester (20.2 g, 72.3 mmol) was dissolved in acetone (200 ml). Sodium iodide (54 g, 361 mmol) was added and reaction was refluxed under nitrogen for 16 h. After cooling to RT the salts were filtered off. The filtrate was concentrated under vacuum and water (200 ml) was added. The solution was extracted with AcOEt (2 x 100 ml) adding some sat. NaCI to aid phase separation. The organic extracts were pooled and washed with water (100 ml) plus a little sat. NaCI, and sat. NaCI (50 ml_). Dry over MgSO4. The solution was a red-orange color. Three teaspoons of activated charcoal were added. After mixing, the solution was filtered through a bed of celite. The filtrate was concentrated under vacuum to yield a light yellow oil (20.96 g, 89%). HPLC-MS m/z: 327 (M+1 ).1H-NMR (CDCI3, 300 MHz) delta 3.67 (s, 3H), 3.19 (t, 2H), 2.30 (t, 2H), 1.74-1.89 (m, 2H), 1.53-1.70 (m, 2H), 1.34-1.46 (m, 2H), 1.28 (br, 10H).
	With sodium iodide; In acetone; for 4h;Reflux; Inert atmosphere; Schlenk technique;	A suspension of <strong>[6287-90-7]methyl 11-bromoundecanoate</strong> (2.88g, 10.30mmol) and sodium iodide (4.77g, 31.82mmol) in acetone (100mL) was heated under reflux for 4h. After cooling to room temperature, the white salt was filtered off. The filtrate was concentrated under reduced pressure, then water (50mL) was added. The mixture was extracted with dichloromethane. The combined organic extracts were washed successively with 10wt% aqueous sodium thiosulphate and brine, dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure to yield 1 as a light yellow oil (3.18g, 95%) that was used without further purification. TLC (n-hexane-diethyl ether 9:1): Rf 0.35. 1H NMR (400MHz, CDCl3): delta 3.64 (3H, s), 3.16 (2H, t, J=7.0Hz), 2.28 (2H, t, J=7.5Hz), 1.83-1.76 (2H, m), 1.59 (2H, qui, J=7.4Hz), 1.38-1.23 (12H, m). 13C NMR (100MHz, CDCl3): delta 174.4, 51.5, 34.2, 33.6, 30.5, 29.4, 29.3, 29.2, 28.6, 25.0, 7.4. GC: tR 12.2min. EIMS (70eV): m/z (%) 326 (1), 295 (39), 199 (100), 167 (83), 149 (82), 83 (76), 69 (74), 55 (77).

Reference： [1]Bulletin de la Societe Chimique de France,1994,vol. 131,p. 317 - 329
[2]Patent: US2004/6051,2004,A1 .Location in patent: Page/Page column 9
[3]Phytochemistry,2007,vol. 68,p. 925 - 934
[4]Patent: WO2007/128817,2007,A2 .Location in patent: Page/Page column 91
[5]Journal of labelled compounds and radiopharmaceuticals,1978,vol. VOL. 15,p. 451 - 460
[6]Journal of the Chemical Society. Perkin transactions I,1976,p. 465 - 470
[7]Journal of Organometallic Chemistry,2013,vol. 744,p. 144 - 148

6
[ 6287-90-7 ]
[ 141-97-9 ]
[ 2389-02-8 ]

Yield	Reaction Conditions	Operation in experiment
	(i) NaOEt, EtOH, (ii) /BRN= 1771477/, (iii) aq. NaOH; Multistep reaction;

Reference： [1]Kaiser; Lamparsky [Helvetica Chimica Acta, 1978, vol. 61, # 7, p. 2671 - 2680]

7
[ 6287-90-7 ]
[ 1731-86-8 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 3909 - 3911
[2]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 143 - 147

8
[ 6287-90-7 ]
[ 1931-65-3 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 873 - 878
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 4631 - 4639
[3]Journal of labelled compounds and radiopharmaceuticals,1978,vol. VOL. 15,p. 451 - 460
[4]Fitoterapia,2020,vol. 145

9
[ 6287-90-7 ]
[ 3669-80-5 ]

Yield	Reaction Conditions	Operation in experiment
1%	With Amberlyst A-26 carbonate form In 1,4-dioxane at 60℃; for 24h;

Reference： [1]Ruddick, Clare L.; Hodge, Philip; Houghton, Mark P. [Synthesis, 1996, # 11, p. 1359 - 1362]

10
[ 6287-90-7 ]
[ 75238-29-8 ]
[ 254966-03-5 ]

Reference： [1]Journal of the American Chemical Society,1999,vol. 121,p. 11425 - 11431

11
[ 6287-90-7 ]
[ 28165-52-8 ]
[ 305350-58-7 ]

Reference： [1]Organic Letters,2000,vol. 2,p. 3189 - 3192

12
[ 6287-90-7 ]
[ 70346-51-9 ]
3-[1-(10-methoxycarbonyl-decyl)-1<i>H</i>-imidazol-4-yl]-acrylic acid methyl ester [ No CAS ]

Reference： [1]Heterocycles,2000,vol. 53,p. 2509 - 2515

13
[ 6287-90-7 ]
[ 123-08-0 ]
[ 613257-46-8 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 6633 - 6634
[2]Chemistry Letters,2008,vol. 37,p. 404 - 405
[3]Inorganic Chemistry,2015,vol. 54,p. 7368 - 7380

14
[ 6287-90-7 ]
[ 540-38-5 ]
[ 372163-16-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium carbonate; In acetone; for 48h;Heating / reflux;	(a) Preparation of methyl 11- (4-iodophenoxy) undecanoate (10); Methyl 11-bromoundecanoate (10g, 35. 8mmmol), in acetone (150mut) was treated with 4-iodophenol (7.88g, 35. 8mmol) and potassium carbonate (9.88g 71. 6mmol). The stirred reaction was heated at reflux for 48h. The reaction was then allowed to cool and the reaction concentrated in vacuo to a gum. The reaction was then partitioned between ethyl acetate (150ml) and water (150ml). The ethyl acetate layer was separated dried, over sodium sulfate and concentrated in vacuo to solid. The solid was dissolved in diethyl ether (100ml) and petroleum ether 60-80C (100ml) added. The solution was concentrated in vacuum to a volume of 100mol. The solution was set aside and allowed to crystallise. The product was collected by filtration and dried in vacuum to give 12.22g of solid. The mother liquors were concentrated to No.20ml and allowed to crystallise. A further 0.81 g of solid was collected by filtration. The two solids were combined to give the desired product (13.03 g, 86%) aH (CDCI3) 1.29-1. 78 (16H, m, 3,4, 5,6, 7,8, 9,10- CH2), 2.30 (2H, t, 2-CH2), 3.86 (3H, s, CO2CHa), 3. 90 (2H, t, 11-CH2), 6. 66 (2H, dd, 2, 6- ArH), 7.53 (2H, dd, 3, 5-are, ), No.C (CDCl3) 24. 90. 25. 93, 29. 09, 29. 18, 29. 30, 29. 428 34. 07, 51. 42, 68. 06, 82. 35, 116. 90, 138. 11, 158. 98, and 174.33.

Reference： [1]Patent: WO2005/61415,2005,A1 .Location in patent: Page/Page column 21-22
[2]Macromolecules,2003,vol. 36,p. 5947 - 5959
[3]Chemical Communications,2007,p. 1322 - 1324

15
[ 6287-90-7 ]
[ 136-77-6 ]
[ 869376-48-7 ]
[ 869376-51-2 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 7343 - 7350
[2]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 5406 - 5416

16
[ 6287-90-7 ]
[ 117241-31-3 ]
10-methoxycarbonyldecyl 3,4,5-tris-dodecyloxybenzoate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2005,vol. 11,p. 5126 - 5135

17
[ 6287-90-7 ]
[ 86-93-1 ]
[ 892501-16-5 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 6938 - 6942
[2]Tetrahedron,2006,vol. 62,p. 4838 - 4843

18
[ 6287-90-7 ]
[ 623-33-6 ]
[ 908859-27-8 ]

Yield	Reaction Conditions	Operation in experiment
42%	With triethylamine; In ethanol; for 24h;Heating / reflux;	Example 15b; General Procedure for Amine Alkylation (II); Glycine ethyl ester hydrochloride (2 equiv), triethylamine (4 equiv), and the appropriate aliphatic methyl bromoacetate (1 equiv) were mixed together in ethanol and the reaction mixture was refluxed for 24 h under argon atmosphere. After the solvent removal, the residue was dissolved in water and extracted using dichloromethane. Solvent was removed and the crude reaction mixture was purified through silica-gel column chromatography to get the monoalkylated glycine ester.; Example 15f; According to the general procedure (11), glycine ethyl ester hydrochloride (10 g, 71.6 mmol, 2 equiv), triethylamine (20 mL, 143.2 mmol, 4 equiv), and <strong>[6287-90-7]methyl 11-bromoundecanoate</strong> (10 g, 35.8 mmol, 1 equiv) were mixed together in ethanol and reacted. Solvent was removed and the crude reaction mixture was purified through silica-gel column chromatography by using methanol/ethyl acetate (2:98) as the eluent to get the monosubstituted glycine ester (13). Yield 4.53 g (42%). 1H NMR (400 MHz, CDCl3): delta 4.14 (q, J=7.2 Hz, 2H), 3.61 (s, 3H), 3.34 (s, 2H), 2.53 (t, J=7.2 Hz, 2H), 2.24 (t, J=7.2 Hz, 2H), 1.71 (s, 1H), 1.57-1.52 (m, 2H), 1.44-1.39 (m, 2H), 1.24-1.20 (m, 15H). 13C NMR (100 MHz, CDCl3); delta 174.3, 172.5, 60.6, 51.5, 51.4, 51.3, 51.2, 50.9, 50.8, 49.6, 34.0, 29.9, 29.4, 29.3, 29.1, 29.0, 27.1, 24.8, 14.1. EI/MS m/z (r.i.) 303 (M+2, 5), 302 (M+1, 19), 301 (M+, 100), 270 (5), 228 (46), 196 (5), 116 (19), 84 (8), 55 (5).

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 16224 - 16230
[2]Patent: US2007/293669,2007,A1 .Location in patent: Page/Page column 22; 23

19
[ 6287-90-7 ]
[ 22513-81-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 93.4 percent / LiAlH₄ / diethyl ether / 0.5 h / Heating 2: 91.6 percent / p-toluenesulfonic acid / diethyl ether / 3 h / 19 - 20 °C 3: 90.1 percent / Na / diethyl ether; xylene / 10 h / 25 - 30 °C 4: 97.8 percent / p-toluenesulfonic acid / methanol / 2 h / Heating
	Multi-step reaction with 4 steps 1: 93.4 percent / LiAlH₄ / diethyl ether / 0.5 h / Heating 2: 95 percent / triethylamine / 1 h / 19 - 20 °C 3: 92.2 percent / NaI / acetone / 2 h / Heating 4: 1.) Na; 2.) 3 N H₂SO₄ / 1.) ether, xylene, 35 -40 deg C, 10 h

Reference： [1]Rusanova, E. E.; Sebyakin, Yu. L.; Volkova, L. V.; Evstigneeva, R. P. [Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 248 - 251][Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 2, p. 279 - 282]
[2]Rusanova, E. E.; Sebyakin, Yu. L.; Volkova, L. V.; Evstigneeva, R. P. [Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 248 - 251][Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 2, p. 279 - 282]

20
[ 6287-90-7 ]
[ 2389-02-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NaH / tetrahydrofuran; dimethylformamide / 2 h / Heating 2: 87 percent / conc. HCl / methanol; H₂O / 9 h / Heating

Reference： [1]Clyne, Dean S.; Weiler, Larry [Tetrahedron, 1999, vol. 55, # 48, p. 13659 - 13682]

21
[ 6287-90-7 ]
[ 34010-21-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 22 g / acetonitrile / 8 h / Heating 2: 1.) potassium tert-butanolate / 1.) DMF, 20 deg C, 3h, 2.) 5h 3: LiAlH₄ / diethyl ether / 3 h / Heating 4: pyridine / 10 h / Ambient temperature

Reference： [1]Dzhemilev, U. M.; Balezina, G. G.; Volkova, L. A.; Krivonogov, V. P.; Tolstikov, G. A. [Chemistry of Natural Compounds, 1980, vol. 16, # 1, p. 82 - 85][Khimiya Prirodnykh Soedinenii, 1980, vol. 16, # 1, p. 97 - 102]

22
[ 6287-90-7 ]
[ 20711-10-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 22 g / acetonitrile / 8 h / Heating 2: 1.) potassium tert-butanolate / 1.) DMF, 20 deg C, 3h, 2.) 5h 3: LiAlH₄ / diethyl ether / 3 h / Heating 4: pyridine / 10 h / Ambient temperature

23
[ 6287-90-7 ]
[ 17278-73-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: (i) NaOEt, EtOH, (ii) /BRN= 1771477/, (iii) aq. NaOH 3: (i) NaBH₄, Na₂HPO₄*2H₂O, aq. EtOH, (ii) aq. KOH

Reference： [1]Kaiser; Lamparsky [Helvetica Chimica Acta, 1978, vol. 61, # 7, p. 2671 - 2680]

24
[ 6287-90-7 ]
[ 6272-38-4 ]
[ 870287-31-3 ]

Yield	Reaction Conditions	Operation in experiment
93%		Compound 177 - 11-(2-Benzyloxyphenoxy)undecanoic acid:; [349] To a 250 mL Erienmeyer flask was added freshly ground potassium hydroxide (4.2 g, 74.91 mmol) and 100 mL dimethyl sulfoxide. 2-benzyloxy-phenol (5 g, 24.97 mmol) and <strong>[6287-90-7]11-bromoundecanoic acid methyl ester</strong> (7 g, 25.07 mmol) was added and the mixture was allowed to stir at room temperature overnight. Water (75 mL) was added and the solution was heated to 85C , with stirring, for 3 hours. The reaction was cooled to room temperature and acidified with concentrated hydrochloric acid to pH 2. The acidified solution was cooled to 4C for 2 hours, and the precipitate then collect by suction filtration. The product was recrystallized form ethanol/water. The product (8.88 g, 93%) was isolated as a light brown solid, mp 62-63C. Combustion analysis: Found: C 74.71 H 8.08%; C24H3204 requires C 74.97, H 8.39 %;

Reference： [1]Patent: WO2005/112633,2005,A2 .Location in patent: Page/Page column 97

25
sodium borohydrid [ No CAS ]
[ 6287-90-7 ]
[ 1611-56-9 ]

Yield	Reaction Conditions	Operation in experiment
98.9%	With hydrogenchloride;aluminium trichloride; In diethylene glycol dimethyl ether; water;	(2) Sodium Borohydride (16.32 g, 0.43 mole) was dissolved in diglyme (350 ml). To this was added a solution of aluminium trichloride (19.2 g, 0.14 mole) in diglyme (250 ml) maintaining the temperature below 20. After the addition was complete, the mixture was stirred for 0.5 hour at room temperature. The reducing agent was then added dropwise to a solution of <strong>[6287-90-7]methyl 11-bromoundecanoate</strong>* (120 g, 0.43 mole) in diglyme (200 ml) maintaining the temperature at 10. After the addition was complete the reaction was stirred at 20 for 3 hours and then quenched by pouring onto water (2 L) and concentrated HCl (100 ml). The quenched mixture was stirred for 1 hour then cooled to 15. The product was filtered off, washed with water (2500 ml) and dried under vacuum to give 11-bromoundecanol (106.8 g, 98.9%). This methyl ester can be produced in quantitative yield by esterifying 11-bromoundecanoic acid with MeOH/H2 SO4

Reference： [1]Patent: US5441731,1995,A

26
[ 6287-90-7 ]
[ 5137-55-3 ]
[ 507-09-5 ]
methyl 11-thioacetylundecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With caesium carbonate; In dichloromethane; water;	Methyl 11-thioacetylundecanoate 104 Compound 103 (17.8 g, 64 mmol), thioacetic acid (9.7 g, 9.0 ml, 128 mmol), methyltrioctylammonium chloride (0.5 g), cesium carbonate (25 g, 77 mmol), dichloromethane (95 ml) and water (95 ml) were stirred at room temperature for 15 h. The reaction was monitored by TLC (SiO2, ethyl acetate:isooctane, 1:5). The mixture was extracted with dichloromethane and the combined extracts were dried (Na2 SO4) and concentrated. Distillation gave pure 104 (15.6 g, 89%) with b.p. 137-139 (0.1 torr) and m.p. <25 (from isooctane). 1 H-NMR (CDCl3, Me4 Si) delta 3.67 (s, 3H, MeO), 2.86 (t, 2H, J=7.1 Hz, S--CH2), 2.32 (s, 3H, MeCO), 2.30 (t, 2H, J=7.7 Hz, CH2 CO). 13 C-NMR (CDCl3, Me4 Si) delta 195.9, 174.1 (CO), 51.3, 34.0, 30.5, 29.4, 29.3, 29.2, 29.1, 29.0, 28.9, 28.7, 24.8. Anal. Calc. for C14 H26 O3 S: C, 61.27; H, 9.50. Found: C, 60.80; H, 9.79.

Reference： [1]Patent: US4675392,1987,A

27
[ 40786-69-4 ]
[ 6287-90-7 ]
11-(4-acetyl-3-hydroxy-2-propylphenoxy)-undecanoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium carbonate; In N,N-dimethyl-formamide;	EXAMPLE 13 Preparation of 11-(4-Acetyl-3-hydroxy-2-propylphenoxy)undecanoic acid methyl ester A mixture of 1.00 g of 1-(2,4-dihydroxy-3-propylphenyl)ethanone, 1.44 g of <strong>[6287-90-7]methyl 11-bromoundecanoate</strong> and 1.00 g of anhydrous potassium carbonate in 20 ml of anhydrous dimethyl formamide was stirred and heated at 75 for 2 hours. The usual workup followed by chromatography on 30 g of silica gel and elution with 10% ethyl acetate-toluene gave 1.48 g (76% yield) of 11-(4-Acetyl-3-hydroxy-2-propylphenoxy)undecanoic acid methyl ester, the titled compound, as an oil. Analysis Calculated for C23 H36 O5: C, 70.38; H, 9.24. Found: C, 70.37; H, 9.36.
76%	With potassium carbonate; In N,N-dimethyl-formamide;	EXAMPLE 58 Preparation of 11-(4-Acetyl-3-hydroxy-2-propylphenoxy) undecanoic acid methyl ester. A mixture of 1.00 g of 1-(2,4-dihydroxy-3-propylphenyl) ethanone, 1.44 g of <strong>[6287-90-7]methyl 11-bromoundecanoate</strong> and 1.00 g of anhydrous potassium carbonate in 20 ml of anhydrous dimethyl formamide was stirred and heated at 75 for 2 hours. The usual workup followed by chromatography on 30 g of silica gel and elution with 10% ethyl acetate-toluene gave 1.48 g (76% yield) of 11-(4-Acetyl-3-hydroxy-2-propylphenoxy) undecanoic acid methyl ester, the titled compound, as an oil. Analysis Calculated for C23 H36 O5: C, 70.38; H, 9.24. Found: C, 70.37; H, 9.36.

Reference： [1]Patent: US4628115,1986,A
[2]Patent: US4672066,1987,A

28
[ 14813-85-5 ]
[ 6287-90-7 ]
[ 83421-94-7 ]

Yield	Reaction Conditions	Operation in experiment
	With NaH; In N,N-dimethyl-formamide; mineral oil;	EXAMPLE 12 11-(2-Oxo-3-phenyl-benzimidazolin-1-yl)-undecanoic acid methyl ester The product is produced as described in example 1 from 1.3 g. of NaH (80% suspension in mineral oil), 10 g. of 1-phenylbenzimidazolin-2-one, 200 cc. of DMF, 13.3 g. of 11-bromoundecanoic acid methyl ester and 1.3 g. of NaJ. Eluant in chromatographic purification: hexane/ethylacetate. Yield: 15.8 g. Fp.: 74 C. IR (in KBr): 1735 and 1705 cm-1.

Reference： [1]Patent: US4377695,1983,A

29
Sodium 4-[3R,4R-dihydroxy-5S(2S,3S-epoxy-5S-hydroxy-4S-methylhexyl)-2,3,5,6-tetrahydropyran-2S-yl]-3-methylbut-2E-enoate [ No CAS ]
[ 6287-90-7 ]
10-Methoxycarbonyldecyl 4-[3R,4R-dihydroxy5S-(2S,3S-epoxy-5S-hydroxy-4S-methylhexyl)-2,3,5,6-tetrahydropyran-2S-yl]-3-methylbut-2E-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With N,N,N,N,N,N-hexamethylphosphoric triamide; In N-methyl-acetamide;	EXAMPLE 13 Preparation of 10-Methoxycarbonyldecyl 4-[3R,4R-dihydroxy5S-(2S,3S-epoxy-5S-hydroxy-4S-methylhexyl)-2,3,5,6-tetrahydropyran-2S-yl]-3-methylbut-2E-enoate (10-Methoxycarbonyldecyl monate) The sodium salt of 4-[3R,4R-dihydroxy-5S-(2S,3S-epoxy-5S-hydroxy-4S-methylhexyl)-2,3,5,6-tetrahydropyran-2S-yl]-3-methylbut2E-enoic acid (0.750gm; 2.05mM) was dissolved in dry dimethylformamide (25ml) and stirred at room temperature for 18 hours with <strong>[6287-90-7]methyl 11-bromoundecanoate</strong> (1.145gm; 4.10mM) and hexamethylphosphoramide (25 drops). The solvent was then removed at reduced pressure and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was washed with saturated sodium solution and dried over anhydrous magnesium sulphate. Filtration and removal of solvent at reduced pressure gave a pale yellow oil, which partially crystallized on standing (1.84gm). Column chromatography over silica gel (Type 60; 75gm), eluding with 5% methanol/chloroform gave the pure 10-methoxycarbonyldecyl monat (hplc and tlc) as a colourless oil. Trituration with dry ether gave a white solid (0.619gm; 56%). m.pt. 75-76 C. (ethyl acetate/hexane). (Found: C, 64.23; H, 9.47. C29 H50 O9 requires: C, 64.18; H, 9.29%). [alpha]D20 - 748 (c, 1% CHCl3). lambdamax (EtOH) 222nm (epsilonm 13,400). numax (CHBr3) 3450, 1739, 1710 and 1645cm-1. deltaH (CDCl3) 5.70 (1H,s,CH=C); 3.61 (3H,s,CO2 CH3); 2.18 (3H,s, CH3 - C=C; 0.91 (3H,d,J = 6.Hz CHCH3). deltaC (CDCl3) 174.4, 166.8, 156.6, 117.7, 74.9, 70.4, 69.1, 65.9, 61.3, 55.6, 51.4, 42.8, 39.5, 117.7, 34.1, 31.7, 29.2, 28.7, 26.0, 25.0, 20.8, 19.1, 12.7, m/e 524 (1.5%; M+ - H2 O), 440 (1%; - C5 H10 O2), 327 (>5%, M+ --O(CH2)10 CO2 CH3), 309 (2%, 327 - H2 O), 298 (22%; [H2 C:C(CH3).CH2 CO2 (CH2)10 CO2 CH3 ]+), 227 (100%), 209 (15%; 227 - H2 O), no M+.

Reference： [1]Patent: US4102901,1978,A

30
[ 6287-90-7 ]
[ 128322-48-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; In dimethyl sulfoxide; at 66℃; for 48h;	Synthesis of 11-azido-undecanoic acid methyl ester: A mixture of 13.3 g of <strong>[6287-90-7]methyl 11-bromoundecanoate</strong> and 3.12 g of sodium azide in 50 mL of DMSO was heated at 66 C under nitrogen for 2 days. The reaction mixture was cooled down and mixed with 20OmL of ice water. The aqueous layer was extracted with ether (1x100 mL, subsequently 3x 50 mL). The organic layers were combined, washed twice with 25 mL of brine and dried over Na2SO4. Removal of the solvents in vacuo gave 11.2 g of a yellow oil. Purification by column chromatography (silica gel; petroleum ether (40-60 C)/ether = 9:1 (v/v)) gave 10.94 g of the pure product as a colorless oil, which was stored at 4 0C to prevent degradation. 1H NMR (300MHz, CDCl3): delta 3.65 (s, 3H); 3.24 (t, 2H, J = 7.0 Hz); 2.29 (t, 2H, J = 7.5 Hz); 1.65-1.53 (m, 2H); 1.42-1.21 (m, 14H) ppm. 13C NMR (75MHz, CDCl3): <n="74"/>delta 174.24; 51.44; 51.37; 34.04; 29.35; 29.27; 29.15; 29.07; 28.80; 26.66; 24.89 ppm. IR (neat, cm"1): 2929 (m); 2856 (m); 2096 (s); 1741 (s).

Reference： [1]Chemical Communications,2008,p. 4001 - 4003
[2]European Journal of Medicinal Chemistry,2018,vol. 148,p. 314 - 324
[3]Patent: WO2008/67436,2008,A2 .Location in patent: Page/Page column 72-73

31
[ 6287-90-7 ]
[ 56469-10-4 ]
[ 1150586-44-9 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 2506 - 2514

32
[ 6287-90-7 ]
[ 3004-42-0 ]
methyl 11-[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]undecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate; In N,N-dimethyl-formamide; for 24h;Heating;	To a solution of 5-phenyl-1,3,4-oxadiazole-2(3H)-thione (2.68 g,15.04 mmol) in DMF (20 mL), <strong>[6287-90-7]methyl-11-bromoundecanoate</strong> (4.2 g, 15.04 mmol) and K2CO3 (4 g, 30.39 mmol) were added. The contents of the flask were stirred and heated for 24 h. Thereafter, the reaction mixture was cooled and cold water was added. The precipitated solid product was filtered, washed with water and dried at room temperature for 24 h. It was crystallized from hexane/AcOEt as a cream-colored solid. Yield 4.4 g(78%); mp 62-63C. IR (KBr): 3063, 1737, 1555. 1H NMR (400 MHz, CDCl3) delta8.02-8.00 (m, 2H, Ar), 7.53-7.47 (m, 2H, Ar), 3.67 (s, 3H, -OCH3), 3.30 (t, J = 7.6 Hz,2H, hetSCH2CH2-), 2.30 (t, J = 7.2 Hz, 2H, CH3OC OCH2CH2-), 1.84 (quin, J =7.2 Hz, 2H, hetSCH2CH2CH2-), 1.46 (quin, J = 7.6 Hz, 2H, CH3OC OCH2CH2CH2-),1.37-1.25 (m, 12H, CH2-). 13C NMR (100 MHz, CDCl3) delta 174.4, 165.6, 164.6, 131.6,129.0, 126.6, 123.7, 51.5, 34.1, 32.6, 29.4, 29.3, 29.2 (2C), 29.1, 29.0, 28.6, 24.9. Analcalc for C20H28N2O3S (376.51): C 63.80, H 7.50, N 7.44, S 8.52. Found: C 63.80, H 7.67,N 7.23, S 8.05.

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2015,vol. 190,p. 1535 - 1550

33
[ 111-26-2 ]
[ 6287-90-7 ]
methyl 11-(hexylamino)undecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85.2%	With potassium carbonate; In N,N-dimethyl-formamide; at 90 - 110℃; for 12h;	General procedure: Methyl 11-bromoundecanoate (1.0 equivalent) and amine (1.1 equivalents) were dissolved in DMF solvent and stirred for 15 minutes, followed by the addition of K2CO3 base catalyst (2 equivalents to <strong>[6287-90-7]methyl 11-bromoundecanoate</strong>) and the reaction was continued at 90-110 C for 12 h. The progress of the reaction was monitored by TLC using CHCl3 and methanol (90:10 v/v) as a solvent system. After completion of the reaction, the catalyst K2CO3 was filtered followed by washing with water and the crude product was extracted by ethyl acetate. Pure methyl 11-(alkylamino) undecanoates (3a-c) were separated out from the dried crude reaction product by column chromatography using silica gel (60-120 mesh) with chloroform and methanol (98:2, v/v) as eluent. Column chromatography was monitored by TLC using chloroform and methanol (9:1, v/v) solvent system and the product was identified by iodine vapour. The isolated yields were in the range of 85.0-90.0%. Spectral data of methyl 11-(alkylamino) undecanoate (3a-c)Methyl 11-(hexylamino) undecanoate (3a)Light yellow liquid; Yield: 85.2%; IR (Neat, cm-1): 3428, 2926, 2855, 1742, 1467, 1167; 1H-NMR (CDCl3, 500 MHz) delta ppm: 3.67 (s, 3H), 2.59 (t, J = 7.1 Hz, 4H), 2.30 (t, J = 7.5 Hz, 2H), 2.0 (s, 1H), 1.68-1.56 (m, 2H), 1.54-1.41 (m, 4H), 1.38-1.21 (m, 18H), 0.88 (t, J = 6.8 Hz, 3H); 13C-NMR (CDCl3, 75 MHz) delta ppm: 174.0 (-C=O), 51.2 (2 X (-N-CH2)), 49.9 (-CO-CH3), 33.9, 31.8, 30.0, 29.5, 29.4, 29.2, 29.1, 29.0, 27.3, 24.8, 22.5, 13.9; ESI-MS (m/z) (M+H)+ 300.51; HRMS-ESI (m/z) calculated for (C18H37NO2+H)+ is 300.2897, found at 300.2889.
	With potassium carbonate; In N,N-dimethyl-formamide; at 90 - 110℃; for 12h;	General procedure: Initially, 11-bromoundecanoic acid (1) was converted into11-bromoundecanoate (11-BUME) (2) by reacting with methanol in presence of PTSA. Later, 11-BUME (1.0 eq) and amine (hexyl, dodecyl, and octadecyl amine; 1.1 eq)were dissolved in DMF solvent and stirred for 10 min followedby the addition of anhydrous K2CO3 (2 eqs to 11-BUME), and the reaction was continued at 90110 C for12 h. The progress of the reaction was monitored by TLCusing CHCl3 and methanol (90:10 v/v) as a solvent system.After completion of the reaction, the catalyst K2CO3 wasfiltered from the crude reaction product and extracted withethyl acetate followed by washing with water to remove theDMF solvent. The crude reaction product was dried bypassing through anhydrous sodium sulfate and the ethylacetate solvent was removed under reduced pressure byusing rotary evaporator. Pure methyl 11-(alkylamino)undecanoate was separated out from the dried crude reactionproduct by column chromatography using silica gel(60-120 mesh) with chloroform and methanol (98:2, v/v) aseluent. Column chromatography was monitored by TLCusing chloroform and methanol (9:1, v/v) solvent systemand the product was identified by iodine vapor. The detailedcharacterization of methyl 11-(alkylamino) undecanoates(3a-c) has been reported by us previously (Yasa et al.2016). The isolated yields were in the range of 85.090.0%.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1978 - 1982
[2]Medicinal Chemistry Research,2017,vol. 26,p. 2592 - 2601

34
[ 111-26-2 ]
[ 6287-90-7 ]
dimethyl 11,11'-(hexylazanediyl)diundecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90.5%	With potassium carbonate; In N,N-dimethyl-formamide; at 90 - 110℃; for 12h;	General procedure: Methyl 11-bromo undecanoate (1 equivalent) and amine (0.55 equivalents) were dissolved in DMF solvent and stirred for 15 minutes, followed by the addition of K2CO3 base catalyst (2 equivalents to methyl 11-bromo undecanoate). The reaction temperature was raised to 90-110 C and continued for 12 h upto the completion of the starting material, methyl 11-bromo undecanoate. The progress of the reaction was monitored by TLC using CHCl3 and methanol (9:1, v/v) solvent system. The reaction mixture was worked up by filtering the base catalyst K2CO3 followed by washing with water and the crude reaction product was extracted using ethyl acetate. Pure dimethyl 11,11'-(alkylazanediyl) diundecanoate was separated from the crude product by column chromatography using silica gel (60-120 mesh) with chloroform and methanol (99:1, v/v) solvent system as eluent. Isolated yields were in the range of 88.0-91.0%. Spectral data of dimethyl 11,11'-(alkylazanediyl) diundecanoateDimethyl 11,11'-(hexylazanediyl) diundecanoate (3d)Light yellow liquid; Yield 90.5%; IR (Neat, cm-1): 2927, 2855, 1741, 1462, 1171; 1H-NMR (CDCl3, 300 MHz) delta ppm: 3.67 (s, 6H), 2.44 (bt, J = 7.5 Hz, 6H), 2.30 (t, J = 7.5 Hz, 4H), 1.66-1.57 (m. 4H), 1.50-1.39 (m, 6H), 1.36-1.20 (m, 30H), 0.88 (t, J = 7.0 Hz, 3H); 13C-NMR (CDCl3, 75 MHz) delta ppm: 174.2 (-C=O), 53.2 (3 X (-N-CH2)), 51.4 (-CO-CH3), 34.0, 31.5, 29.4, 29.3, 29.3, 29.1, 29.0, 27.3, 27.0, 25.3, 24.9, 22.5, 13.9; ESI-MS (m/z) (M+H)+ 498.55; HRMS-ESI (m/z) calculated for (C30H59NO4+H)+ is 498.4517, found at 498.4493.
		General procedure: Synthesis of dimethyl 11,11?-(alkylazanediyl) diundecanoateswas performed by reported method (Yasa et al. 2016).Initially, 11-bromo undecanoic acid was converted into<strong>[6287-90-7]methyl 11-bromoundecanoate</strong> (11-BUME). Further, 11-BUME (1 eq) and amine (0.55 eqs) were dissolved in DMFsolvent and stirred for 15 min, followed by the addition ofanhydrous K2CO3 catalyst (2 eqs to 11-BUME). The reactiontemperature was raised to 110 C and continued for 12h until complete conversion of starting material, 11-BUMEas shown in Scheme 1. The progress of the reaction wasmonitored by TLC using solvent system of CHCl3 andmethanol (9:1 v/v). The crude reaction product was filteredto separate K2CO3 followed by washing with water andextraction with ethyl acetate. Pure dimethyl 11,11?-(alkylazanediyl)diundecanoates (3a-c) was separated from crudeproduct by silica gel (60-120 mesh) column chromatographyusing chloroform and methanol (99:1, v/v) solventsystem as eluent. Isolated yields were in the range of88-93%.
	With potassium carbonate; In N,N-dimethyl-formamide; at 90 - 110℃; for 12h;	General procedure: 11-BUME (1 eq) and amine (0.55 eq) were dissolved inDMF solvent and stirred for 10 min followed by the additionof K2CO3, base catalyst (2 eqs to 11-BUME), and thereaction continued at 90-110 C for 12 h. After completionof the reaction, the catalyst K2CO3 was filtered from crudereaction product and extracted with ethyl acetate followedby washing with water to remove DMF solvent. Puredimethyl 11,11?-(alkylazanediyl)diundecanoate was separatedout from the crude product by column chromatographyusing silica gel (60-120 mesh) with chloroform andmethanol (99:1, v/v) as eluent. The detailed characterizationof dimethyl 11,11?-(alkylazanediyl) diundecanoates (3d-f)has been reported by us previously (Yasa et al. 2016). Theisolated yields were in the range of 88.091.5%.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1978 - 1982
[2]Medicinal Chemistry Research,2017,vol. 26,p. 1689 - 1696
[3]Medicinal Chemistry Research,2017,vol. 26,p. 2592 - 2601

35
[ 124-22-1 ]
[ 6287-90-7 ]
methyl 11-(dodecylamino)undecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89.1%	With potassium carbonate; In N,N-dimethyl-formamide; at 90 - 110℃; for 12h;	General procedure: Methyl 11-bromoundecanoate (1.0 equivalent) and amine (1.1 equivalents) were dissolved in DMF solvent and stirred for 15 minutes, followed by the addition of K2CO3 base catalyst (2 equivalents to <strong>[6287-90-7]methyl 11-bromoundecanoate</strong>) and the reaction was continued at 90-110 C for 12 h. The progress of the reaction was monitored by TLC using CHCl3 and methanol (90:10 v/v) as a solvent system. After completion of the reaction, the catalyst K2CO3 was filtered followed by washing with water and the crude product was extracted by ethyl acetate. Pure methyl 11-(alkylamino) undecanoates (3a-c) were separated out from the dried crude reaction product by column chromatography using silica gel (60-120 mesh) with chloroform and methanol (98:2, v/v) as eluent. Column chromatography was monitored by TLC using chloroform and methanol (9:1, v/v) solvent system and the product was identified by iodine vapour. The isolated yields were in the range of 85.0-90.0%.
	With potassium carbonate; In N,N-dimethyl-formamide; at 90 - 110℃; for 12h;	General procedure: Initially, 11-bromoundecanoic acid (1) was converted into11-bromoundecanoate (11-BUME) (2) by reacting with methanol in presence of PTSA. Later, 11-BUME (1.0 eq) and amine (hexyl, dodecyl, and octadecyl amine; 1.1 eq)were dissolved in DMF solvent and stirred for 10 min followedby the addition of anhydrous K2CO3 (2 eqs to 11-BUME), and the reaction was continued at 90110 C for12 h. The progress of the reaction was monitored by TLCusing CHCl3 and methanol (90:10 v/v) as a solvent system.After completion of the reaction, the catalyst K2CO3 wasfiltered from the crude reaction product and extracted withethyl acetate followed by washing with water to remove theDMF solvent. The crude reaction product was dried bypassing through anhydrous sodium sulfate and the ethylacetate solvent was removed under reduced pressure byusing rotary evaporator. Pure methyl 11-(alkylamino)undecanoate was separated out from the dried crude reactionproduct by column chromatography using silica gel(60-120 mesh) with chloroform and methanol (98:2, v/v) aseluent. Column chromatography was monitored by TLCusing chloroform and methanol (9:1, v/v) solvent systemand the product was identified by iodine vapor. The detailedcharacterization of methyl 11-(alkylamino) undecanoates(3a-c) has been reported by us previously (Yasa et al.2016). The isolated yields were in the range of 85.090.0%.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1978 - 1982
[2]Medicinal Chemistry Research,2017,vol. 26,p. 2592 - 2601

36
[ 124-22-1 ]
[ 6287-90-7 ]
dimethyl 11,11'-(dodecylazanediyl)diundecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate; In N,N-dimethyl-formamide; at 90 - 110℃; for 12h;	General procedure: Methyl 11-bromo undecanoate (1 equivalent) and amine (0.55 equivalents) were dissolved in DMF solvent and stirred for 15 minutes, followed by the addition of K2CO3 base catalyst (2 equivalents to methyl 11-bromo undecanoate). The reaction temperature was raised to 90-110 C and continued for 12 h upto the completion of the starting material, methyl 11-bromo undecanoate. The progress of the reaction was monitored by TLC using CHCl3 and methanol (9:1, v/v) solvent system. The reaction mixture was worked up by filtering the base catalyst K2CO3 followed by washing with water and the crude reaction product was extracted using ethyl acetate. Pure dimethyl 11,11'-(alkylazanediyl) diundecanoate was separated from the crude product by column chromatography using silica gel (60-120 mesh) with chloroform and methanol (99:1, v/v) solvent system as eluent. Isolated yields were in the range of 88.0-91.0%.
		General procedure: Synthesis of dimethyl 11,11?-(alkylazanediyl) diundecanoateswas performed by reported method (Yasa et al. 2016).Initially, 11-bromo undecanoic acid was converted into<strong>[6287-90-7]methyl 11-bromoundecanoate</strong> (11-BUME). Further, 11-BUME (1 eq) and amine (0.55 eqs) were dissolved in DMFsolvent and stirred for 15 min, followed by the addition ofanhydrous K2CO3 catalyst (2 eqs to 11-BUME). The reactiontemperature was raised to 110 C and continued for 12h until complete conversion of starting material, 11-BUMEas shown in Scheme 1. The progress of the reaction wasmonitored by TLC using solvent system of CHCl3 andmethanol (9:1 v/v). The crude reaction product was filteredto separate K2CO3 followed by washing with water andextraction with ethyl acetate. Pure dimethyl 11,11?-(alkylazanediyl)diundecanoates (3a-c) was separated from crudeproduct by silica gel (60-120 mesh) column chromatographyusing chloroform and methanol (99:1, v/v) solventsystem as eluent. Isolated yields were in the range of88-93%.
	With potassium carbonate; In N,N-dimethyl-formamide; at 90 - 110℃; for 12h;	General procedure: 11-BUME (1 eq) and amine (0.55 eq) were dissolved inDMF solvent and stirred for 10 min followed by the additionof K2CO3, base catalyst (2 eqs to 11-BUME), and thereaction continued at 90-110 C for 12 h. After completionof the reaction, the catalyst K2CO3 was filtered from crudereaction product and extracted with ethyl acetate followedby washing with water to remove DMF solvent. Puredimethyl 11,11?-(alkylazanediyl)diundecanoate was separatedout from the crude product by column chromatographyusing silica gel (60-120 mesh) with chloroform andmethanol (99:1, v/v) as eluent. The detailed characterizationof dimethyl 11,11?-(alkylazanediyl) diundecanoates (3d-f)has been reported by us previously (Yasa et al. 2016). Theisolated yields were in the range of 88.091.5%.

37
[ 6287-90-7 ]
[ 124-30-1 ]
methyl 11-(octadecylamino)undecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate; In N,N-dimethyl-formamide; at 90 - 110℃; for 12h;	General procedure: Methyl 11-bromoundecanoate (1.0 equivalent) and amine (1.1 equivalents) were dissolved in DMF solvent and stirred for 15 minutes, followed by the addition of K2CO3 base catalyst (2 equivalents to <strong>[6287-90-7]methyl 11-bromoundecanoate</strong>) and the reaction was continued at 90-110 C for 12 h. The progress of the reaction was monitored by TLC using CHCl3 and methanol (90:10 v/v) as a solvent system. After completion of the reaction, the catalyst K2CO3 was filtered followed by washing with water and the crude product was extracted by ethyl acetate. Pure methyl 11-(alkylamino) undecanoates (3a-c) were separated out from the dried crude reaction product by column chromatography using silica gel (60-120 mesh) with chloroform and methanol (98:2, v/v) as eluent. Column chromatography was monitored by TLC using chloroform and methanol (9:1, v/v) solvent system and the product was identified by iodine vapour. The isolated yields were in the range of 85.0-90.0%.
	With potassium carbonate; In N,N-dimethyl-formamide; at 90 - 110℃; for 12h;	General procedure: Initially, 11-bromoundecanoic acid (1) was converted into11-bromoundecanoate (11-BUME) (2) by reacting with methanol in presence of PTSA. Later, 11-BUME (1.0 eq) and amine (hexyl, dodecyl, and octadecyl amine; 1.1 eq)were dissolved in DMF solvent and stirred for 10 min followedby the addition of anhydrous K2CO3 (2 eqs to 11-BUME), and the reaction was continued at 90110 C for12 h. The progress of the reaction was monitored by TLCusing CHCl3 and methanol (90:10 v/v) as a solvent system.After completion of the reaction, the catalyst K2CO3 wasfiltered from the crude reaction product and extracted withethyl acetate followed by washing with water to remove theDMF solvent. The crude reaction product was dried bypassing through anhydrous sodium sulfate and the ethylacetate solvent was removed under reduced pressure byusing rotary evaporator. Pure methyl 11-(alkylamino)undecanoate was separated out from the dried crude reactionproduct by column chromatography using silica gel(60-120 mesh) with chloroform and methanol (98:2, v/v) aseluent. Column chromatography was monitored by TLCusing chloroform and methanol (9:1, v/v) solvent systemand the product was identified by iodine vapor. The detailedcharacterization of methyl 11-(alkylamino) undecanoates(3a-c) has been reported by us previously (Yasa et al.2016). The isolated yields were in the range of 85.090.0%.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1978 - 1982
[2]Medicinal Chemistry Research,2017,vol. 26,p. 2592 - 2601

38
[ 6287-90-7 ]
[ 124-30-1 ]
dimethyl 11,11'-(octadecylazanediyl)diundecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88.1%	With potassium carbonate; In N,N-dimethyl-formamide; at 90 - 110℃; for 12h;	General procedure: Methyl 11-bromo undecanoate (1 equivalent) and amine (0.55 equivalents) were dissolved in DMF solvent and stirred for 15 minutes, followed by the addition of K2CO3 base catalyst (2 equivalents to methyl 11-bromo undecanoate). The reaction temperature was raised to 90-110 C and continued for 12 h upto the completion of the starting material, methyl 11-bromo undecanoate. The progress of the reaction was monitored by TLC using CHCl3 and methanol (9:1, v/v) solvent system. The reaction mixture was worked up by filtering the base catalyst K2CO3 followed by washing with water and the crude reaction product was extracted using ethyl acetate. Pure dimethyl 11,11'-(alkylazanediyl) diundecanoate was separated from the crude product by column chromatography using silica gel (60-120 mesh) with chloroform and methanol (99:1, v/v) solvent system as eluent. Isolated yields were in the range of 88.0-91.0%.
		General procedure: Synthesis of dimethyl 11,11?-(alkylazanediyl) diundecanoateswas performed by reported method (Yasa et al. 2016).Initially, 11-bromo undecanoic acid was converted into<strong>[6287-90-7]methyl 11-bromoundecanoate</strong> (11-BUME). Further, 11-BUME (1 eq) and amine (0.55 eqs) were dissolved in DMFsolvent and stirred for 15 min, followed by the addition ofanhydrous K2CO3 catalyst (2 eqs to 11-BUME). The reactiontemperature was raised to 110 C and continued for 12h until complete conversion of starting material, 11-BUMEas shown in Scheme 1. The progress of the reaction wasmonitored by TLC using solvent system of CHCl3 andmethanol (9:1 v/v). The crude reaction product was filteredto separate K2CO3 followed by washing with water andextraction with ethyl acetate. Pure dimethyl 11,11?-(alkylazanediyl)diundecanoates (3a-c) was separated from crudeproduct by silica gel (60-120 mesh) column chromatographyusing chloroform and methanol (99:1, v/v) solventsystem as eluent. Isolated yields were in the range of88-93%.
	With potassium carbonate; In N,N-dimethyl-formamide; at 90 - 110℃; for 12h;	General procedure: 11-BUME (1 eq) and amine (0.55 eq) were dissolved inDMF solvent and stirred for 10 min followed by the additionof K2CO3, base catalyst (2 eqs to 11-BUME), and thereaction continued at 90-110 C for 12 h. After completionof the reaction, the catalyst K2CO3 was filtered from crudereaction product and extracted with ethyl acetate followedby washing with water to remove DMF solvent. Puredimethyl 11,11?-(alkylazanediyl)diundecanoate was separatedout from the crude product by column chromatographyusing silica gel (60-120 mesh) with chloroform andmethanol (99:1, v/v) as eluent. The detailed characterizationof dimethyl 11,11?-(alkylazanediyl) diundecanoates (3d-f)has been reported by us previously (Yasa et al. 2016). Theisolated yields were in the range of 88.091.5%.

39
[ 1120-48-5 ]
[ 6287-90-7 ]
methyl 11-(dioctylamino)undecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate; In N,N-dimethyl-formamide; at 90 - 110℃; for 12h;	General procedure: Methyl 11-bromo undecanoate (2) (1.0 equivalent) and dialkylamine (1.1 equivalents) were dissolved in DMF solvent and stirred for 15 minutes followed by the addition of K2CO3 (2 equivalents to methyl 11-bromo undecanoate) and continued the reaction at 90-110C for 12 h. The progress of the reaction was monitored by TLC using CHCl3 and Methanol (9:1, v/v) solvent system. After completion of the reaction, the K2CO3 catalyst was filtered followed by washing with water and extracted using ethyl acetate. The crude reaction product was dried by passing through anhydrous sodium sulphate and the solvent removed by rotary evaporator. The pure methyl 11-(dialkylamino) undecanoate (3g-h) was separated out from crude reaction product by silica gel (60-120 mesh) column chromatography using chloroform and methanol (98:2, v/v) as eluent. Column chromatography was monitored by TLC using chloroform and methanol (9:1, v/v) solvent system and the product was identified by iodine vapour. Isolated yields were in the range of 95.0-96.0%. Spectral data of methyl 11-(dialkylamino) undecanoate (3g-h)Methyl 11-(dioctylamino) undecanoate (3g)Light yellow liquid; Yield 96.0%; IR (Neat, cm-1): 2926, 2854, 1743, 1463, 1170; 1H-NMR (CDCl3, 300 MHz) delta ppm: 3.67 (s, 3H), 2.48-2.38 (m, 6H), 2.30 (t, J = 7.5 Hz, 4H), 1.65-1.58 (m, 2H), 1.49-1.40 (m, 6H), 1.35-1.20 (m, 32H), 0.88 (t, J = 6.8 Hz, 3H); 13C-NMR (CDCl3, 75 MHz) delta ppm: 174.2 (-C=O), 54.2 (3 X (N-CH2)), 51.3 (-CO-CH3), 34.1, 31.8, 29.6, 29.4, 29.3, 29.2, 29.1, 27.6, 27.0, 24.9, 22.6, 14.0; ESI-MS (m/z) (M+H)+ 440.58; HRMS-ESI (m/z) calculated for (C28H57NO2+H)+ is 440.4462, found at 440.4443.
		General procedure: Synthesis of methyl 11-(dialkylamino) undecanoates wasperformed employing reported method (Yasa et al. 2016).11-BUME (1.0 eq) and dialkylamine (1.1 eqs) were dissolvedin DMF solvent and stirred for 15 min, followed bythe addition of K2CO3 (2 eqs to 11-BUME) and continuedthe reaction for 12 h at 110 C as shown in Scheme 1. Theprogress of the reaction was monitored by TLC usingCHCl3 and Methanol (9:1 v/v) as a solvent system. Thecrude reaction product was worked up by filtering K2CO3followed by washing with water and extracted by ethylacetate, and was dried by passing through anhydroussodium sulphate followed by removal of solvent by rotaryevaporator. Pure methyl 11-(dialkylamino) undecanoate (3dand e) was separated from crude reaction product by columnchromatography using silica gel (60-120 mesh) with chloroform and methanol (98:2, v/v) as eluent. Isolatedyields were in the range of 95-96%.
	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 110℃; for 12h;	General procedure: 11-BUME (1.0 eq) and dialkylamine (1.1 eq) were dissolvedin DMF solvent and stirred for 10 min followed bythe addition of K2CO3 (2 eqs to 11-BUME) at room temperatureand continued the reaction at 90-110 C for 12 h.After completion of the reaction, the catalyst K2CO3 wasfiltered from crude reaction product and extracted with ethylacetate followed by washing with water to remove DMFsolvent. The crude reaction product was dried by passingthrough anhydrous sodium sulfate and the ethyl acetatesolvent was removed under reduced pressure by usingrotary evaporator. The pure methyl 11-(dialkylamino)undecanoate was separated out from the crude reactionproduct by silica gel (60-120 mesh) column chromatographyusing chloroform and methanol (98:2, v/v) as eluent.Column chromatography was monitored by TLC usingchloroform and methanol (9:1, v/v) solvent system and theproduct was identified by iodine vapor. The detailed characterizationof methyl 11-(dialkylamino) undecanoates(3g and 3h) was reported by us previously (Yasa et al.2016). Isolated yields were in the range of 95.096.0%.

40
[ 6287-90-7 ]
[ 101-83-7 ]
methyl 11-(dicyclohexylamino)undecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95.5%	With potassium carbonate; In N,N-dimethyl-formamide; at 90 - 110℃; for 12h;	General procedure: Methyl 11-bromo undecanoate (2) (1.0 equivalent) and dialkylamine (1.1 equivalents) were dissolved in DMF solvent and stirred for 15 minutes followed by the addition of K2CO3 (2 equivalents to methyl 11-bromo undecanoate) and continued the reaction at 90-110C for 12 h. The progress of the reaction was monitored by TLC using CHCl3 and Methanol (9:1, v/v) solvent system. After completion of the reaction, the K2CO3 catalyst was filtered followed by washing with water and extracted using ethyl acetate. The crude reaction product was dried by passing through anhydrous sodium sulphate and the solvent removed by rotary evaporator. The pure methyl 11-(dialkylamino) undecanoate (3g-h) was separated out from crude reaction product by silica gel (60-120 mesh) column chromatography using chloroform and methanol (98:2, v/v) as eluent. Column chromatography was monitored by TLC using chloroform and methanol (9:1, v/v) solvent system and the product was identified by iodine vapour. Isolated yields were in the range of 95.0-96.0%.
		General procedure: Synthesis of methyl 11-(dialkylamino) undecanoates wasperformed employing reported method (Yasa et al. 2016).11-BUME (1.0 eq) and dialkylamine (1.1 eqs) were dissolvedin DMF solvent and stirred for 15 min, followed bythe addition of K2CO3 (2 eqs to 11-BUME) and continuedthe reaction for 12 h at 110 C as shown in Scheme 1. Theprogress of the reaction was monitored by TLC usingCHCl3 and Methanol (9:1 v/v) as a solvent system. Thecrude reaction product was worked up by filtering K2CO3followed by washing with water and extracted by ethylacetate, and was dried by passing through anhydroussodium sulphate followed by removal of solvent by rotaryevaporator. Pure methyl 11-(dialkylamino) undecanoate (3dand e) was separated from crude reaction product by columnchromatography using silica gel (60-120 mesh) with chloroform and methanol (98:2, v/v) as eluent. Isolatedyields were in the range of 95-96%.
	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 110℃; for 12h;	General procedure: 11-BUME (1.0 eq) and dialkylamine (1.1 eq) were dissolvedin DMF solvent and stirred for 10 min followed bythe addition of K2CO3 (2 eqs to 11-BUME) at room temperatureand continued the reaction at 90-110 C for 12 h.After completion of the reaction, the catalyst K2CO3 wasfiltered from crude reaction product and extracted with ethylacetate followed by washing with water to remove DMFsolvent. The crude reaction product was dried by passingthrough anhydrous sodium sulfate and the ethyl acetatesolvent was removed under reduced pressure by usingrotary evaporator. The pure methyl 11-(dialkylamino)undecanoate was separated out from the crude reactionproduct by silica gel (60-120 mesh) column chromatographyusing chloroform and methanol (98:2, v/v) as eluent.Column chromatography was monitored by TLC usingchloroform and methanol (9:1, v/v) solvent system and theproduct was identified by iodine vapor. The detailed characterizationof methyl 11-(dialkylamino) undecanoates(3g and 3h) was reported by us previously (Yasa et al.2016). Isolated yields were in the range of 95.096.0%.

41
[ 6287-90-7 ]
[ 7786-61-0 ]
methyl 11-(2-methoxy-4-vinylphenoxy)undecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate; In acetone;Reflux;	Methyl 11-bromoundecanoate (35 g, 126.6 mmol) and2-methoxy-4-vinylphenol (19 g, 126.6 mmol) were dissolvedin acetone (250 mL), K2CO3 (35 g, 253 mmol) wasadded to the reaction mixture and refluxed overnight. Afterthe completion of the reaction as monitored by TLC, thesolvent was removed under reduced pressure and the crudeproduct was diluted with ethyl acetate (250 mL) and theorganic layer was washed with saturated solution of NaCland dried over Na2SO4. The organic layer was concentratedto dryness. Then the resulting mixture was purifiedby silica gel (eluent l % ethyl acetate in n-hexane) whichafforded methyl 11-(2-methoxy-4-vinylphenoxy)undecanoate(35.26 g, 80 % yield) as a viscous liquid. 1H NMR(300 MHz, CDCl3) delta 7.00-6.89 (m, 2H), 6.82 (d,J = 8.3 Hz, 1H), 6.65 (dd, J = 17.5, 10.7 Hz, 1H), 5.61(d, J = 17.5 Hz, 1H), 5.14 (d, J = 10.7 Hz, 1H), 4.01 (t,J = 6.9 Hz, 2H), 3.89 (s, 3H), 3.67 (s, 3H), 2.30 (t,J = 7.5 Hz, 2H), 1.90-1.77 (m, 2H), 1.69-1.59 (m, 2H),1.51-1.21 (m, 14H). ESI MS: m/z 349.12 [M + 1]+,371.12 [M + Na] +, 387.12 [M + K]+.

Reference： [1]Journal of Surfactants and Detergents,2016,vol. 19,p. 1133 - 1142

42
[ 91-04-3 ]
[ 6287-90-7 ]
methyl 11-(2,6-bis(hydroxymethyl)-4-methylphenoxy)undecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With potassium carbonate; In acetone; for 16h;Reflux;	To a solution of 2,6-bis(hydroxymethyl)-p-cresol (2.7 g, 16.3 mmol), methyl 11- bromoundecanoate (5.0 g, 17.9 mmol) and potassium carbonate (4.5 g, 32.6 mmol) in acetone (100 mL) was refluxed for 16 hours. Upon completion the solution was concentrated in vacuo to dryness, suspended in ethyl acetate (150 mL) and washed with water (2 x 100 mL) and brine (100 mL). The ethyl acetate layer was dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography on silica gel 60 (gradient 100 % Hex - 50% EtO Ac/Hex) to afford methyl 11 -(2,6-bis(hydroxymethyl)-4- methylphenoxy)undecanoate 44 as a colorless oil (1.6 g, 27%).
27%	With potassium carbonate; In acetone; for 16h;Reflux;	To a solution of 2,6-bis(hydroxymethyl)-p-cresol (2.7 g, 16.3 mmol), methyl 11- bromoundecanoate (5.0 g, 17.9 mmol) and potassium carbonate (4.5 g, 32.6 mmol) in acetone (100 mL) was refluxed for 16 hours. Upon completion the solution was concentrated in vacuo to dryness, suspended in ethyl acetate (150 mL) and washed with water (2 x 100 mL) and brine (100 mL). The ethyl acetate layer was dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography on silica gel 60 (gradient 100 % Hex 50% EtO Ac/Hex) to afford methyl 1 l-(2,6-bis(hydroxymethyl)-4- methylphenoxy)undecanoate 44 as a colorless oil (1.6 g, 27%).
27%	With potassium carbonate; In acetone; for 16h;Reflux;	To a solution of 2,6-bis(hydroxymethyl)-p-cresol (2.7 g, 16.3 mmol), methyl 11- bromoundecanoate (5.0 g, 17.9 mmol) and potassium carbonate (4.5 g, 32.6 mmol) in acetone (100 mL) was refluxed for 16 hours. Upon completion the solution was concentrated in vacuo to dryness, suspended in ethyl acetate (150 mL) and washed with water (2 x 100 mL) and brine (100 mL) The ethyl acetate layer was dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography on silica gel 60 (gradient 100 % Hex 50% EtO Ac/Hex) to afford methyl 1 l-(2,6-bis(hydroxymethyl)-4- methylphenoxy)undecanoate 44 as a colorless oil (1.6 g, 27%).

27%

With potassium carbonate; In acetone; for 16h;Reflux;

To a solution of 2,6-bis(hydroxymethyl)-p-cresol (2.7 g, 16.3 mmol), methyl 11- bromoundecanoate (5.0 g, 17.9 mmol) and potassium carbonate (4.5 g, 32.6 mmol) in acetone (100 mL) was refluxed for 16 hours. Upon completion the solution was concentrated in vacuo to dryness, suspended in ethyl acetate (150 mL) and washed with water (2 x 100 mL) and brine (100 mL). The ethyl acetate layer was dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography on silica gel 60 (gradient 100 % Hex 50% EtOAc/Hex) to afford methyl 11-(2,6-bis(hydroxymethyl)-4- methylphenoxy)undecanoate 44 as a colorless oil (1.6 g, 27%).

Reference： [1]Patent: WO2017/177326,2017,A1 .Location in patent: Page/Page column 76; 77
[2]Patent: WO2018/191278,2018,A2 .Location in patent: Page/Page column 102; 103; 104
[3]Patent: WO2019/51257,2019,A2 .Location in patent: Page/Page column 183-184
[4]Patent: WO2020/93061,2020,A1 .Location in patent: Page/Page column 114-116

43
[ 6287-90-7 ]
4-((3-hydroxy-4-methoxyphenyl)(methyl)amino)-2H-chromen-2-one [ No CAS ]
C₂₉H₃₈N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;Inert atmosphere; Cooling with ice;	Under protection of nitrogen gas, dissolve intermediate 15a and N,N-diisopropyl ethylamine in anhydrous dichloromethane, slowly dropwise add dichloromethane solution containing methyl 11-bromo-undecylate while stirring in an ice bath. Then, increase to room temperature to stir overnight. On the next day, remove organic solvent, and carry out flash column chromatography with petroleum ether: ethyl acetate of 8:1 for separation of residual substrate to obtain a light yellow solid, with a yield of 83%. 1H NMR (400 MHz, CDCl3) delta 7.33 (dd, J=11.2, 4.1 Hz, 1H), 7.28 (d, J=5.2 Hz, 1H), 6.98 (d, J=8.3 Hz, 1H), 6.85 (dd, J=11.2, 4.2 Hz, 1H), 6.79 (d, J=8.4 Hz, 1H), 6.66?6.60 (m, 2H), 5.82 (s, 1H), 3.89 (dd, J=12.2, 5.3 Hz, 2H), 3.86 (s, 3H), 3.67 (s, 3H), 3.36 (s, 3H), 2.30 (t, J=7.5 Hz, 2H), 1.82?1.69 (m, 2H), 1.60 (d, J=7.2 Hz, 2H), 1.40 (m, 2H), 1.28 (s, 10H).

Reference： [1]Patent: US2018/282315,2018,A1 .Location in patent: Paragraph 0432-0434

44
[ 6287-90-7 ]
3,5-difluoro-4-((1R,3R)-2-(2-fluoro-2-methylpropyl)-3-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)phenol [ No CAS ]
methyl 11-(3,5-difluoro-4-((1R,3R)-2-(2-fluoro-2-methylpropyl)-3-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)phenoxy)undecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium carbonate; In acetonitrile; at 70℃; for 18h;	Intermediate 32a: Methyl 11-(3,5-difluoro-4-((1R,3R)-2-(2-fluoro-2-methylpropyl)-3-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)phenoxy)undecanoate Methyl 11-bromoundecanoate (158 mg, 0.57 mmol) was added in one portion to 3,5-difluoro-4-((1R,3R)-2-(2-fluoro-2-methylpropyl)-3-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)phenol (200 mg, 0.51 mmol) and potassium carbonate (107 mg, 0.77 mmol) in MeCN (2 mL) at 20 C. under air. The resulting suspension was stirred at 70 C. for 18 hours. The mixture was cooled to RT and was diluted with DCM (10 mL) and water (2 mL). The DCM layer was collected and evaporated to afford crude material as a yellow gum. The crude product was purified by flash silica chromatography, elution gradient 0 to 30% EtOAc in heptane. Pure fractions were evaporated to dryness to afford the title compound (255 mg, 84%) as a colourless gum; 1H NMR (400 MHz, DMSO-d6, 30 C.) 1.05 (3H, d), 1.17 (6H, t), 1.26 (12H, s), 1.46-1.56 (2H, m), 1.63-1.74 (2H, m), 2.29 (2H, t), 2.38 (1H, d), 2.54-2.59 (1H, m), 2.76-2.94 (2H, m), 3.48-3.55 (1H, m), 3.58 (3H, s), 3.97 (2H, t), 5.13 (1H, s), 6.64 (2H, d), 6.97 (2H, m), 7.16-7.21 (1H, m), 7.39 (1H, d), 10.49 (1H, s); m/z: ES+ [M+H]+ 587.4.

Reference： [1]Patent: US2019/194190,2019,A1 .Location in patent: Paragraph 0807; 0808

45
[ 90-33-5 ]
[ 6287-90-7 ]
methyl 11-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)undecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium carbonate; In acetonitrile; at 80℃; for 24h;	General procedure: To a solution of 7-Hydroxy-4-methylcoumarin (3) (5.0 g, 28.3 mmol) in dried CH3CN (50 mL), anhydrous K2CO3 (11.8 g, 84.9 mmol) was added. After stirring for 30 min, methyl 11-bromoacetate (8.7 g, 31.1 mmol) or methyl bromoacetate (5.0 g, 33 mmol) was added to the reaction mixture. The resulting mixture was vigorously stirred at 80 oC for 24 hours under argon gas. After the reaction mixture was cooled to room temperature, the solvent was removed in vacuo. The reaction mixture was acidified with 5 % aqueous HCl solution (100 mL), and then extracted with CH2Cl2 (200 mL). The organic layer was separated and washed with water (100 mL) and dried over anhydrous MgSO4, and the solvent was evaporated to yield a yellow solid. The pure product was isolated by column chromatography on silica gel using ethyl acetate:hexane (1:3) as the eluent. Ethyl 11-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)undecanoate (4). 76% yield; mp 89.3 ; 1H NMR (600 MHz, CDCl3): 7.49 (d, 1H), 6.85 (d, 1H,), 6.80 (s, 1H), 6.12 (s, 1H), 4.0 (t, 2H), 3.66 (s, 3H,), 2.39 (s, 3H), 2.31 (t, 2H), 1.82 (m, 2H,), 1.62 (m, 2H), 1.46 (m, 2H), 1.44 (m, 10H); 13C NMR (600 MHz, CDCl3): 174.25, 162.19, 161.31, 155.2, 152.52, 125.40, 113.35, 112.62, 111.75, 101.30, 68.55, 51.38, 34.05, 29.24, 29.16, 28.93, 25.89, 24.88, 16.60.

Reference： [1]Tetrahedron Letters,2019,vol. 60,p. 2022 - 2025

46
[ 6287-90-7 ]
[ 128143-88-4 ]
C₂₇H₃₃N₃O₃ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2020

47
[ 6287-90-7 ]
[ 1689-82-3 ]
methyl 11-[4-(2-phenyldiazenyl)phenoxy]undecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With potassium carbonate In acetone at 50℃; for 20h; Inert atmosphere;	Methyl 11-[4-(2-phenyldiazenyl)-phenoxy]-undecanoate (1-2d) 1-2 (500 mg, 2.53 mmol, 1 eq.) was dissolved in acetone (15 mL) and potassium carbonate (1.75 g, 12.7 mmol, 5 eq.)And methyl 11-bromoundecanoate (1.84 mL, 2.12 g, 7.58 mmol, 3 eq.) were added, and the mixture was heated under reflux at 50°C.It was allowed to stir under a nitrogen atmosphere for 14 hours.After completion of the reaction, the temperature was returned to room temperature, the solution was filtered, the solvent was distilled off under reduced pressure, diluted with dichloromethane, and washed with water.The washed water was extracted once with dichloromethane, the organic layer was dried over sodium sulfate, the solvent was evaporated under reduced pressure, and the residue was isolated by silica gel chromatography (C-60, hexane:ethyl acetate=25:1), and The product (684 mg, 68%) was obtained as a yellow solid.

Reference： [1]Current Patent Assignee: NATIONAL UNIVERSITY CORPORATION TOKYO INSTITUTE OF TECHNOLOGY - JP2020/83876, 2020, A Location in patent: Paragraph 0073

48
[ 6287-90-7 ]
[ 87345-22-0 ]
5-{4-[(11-methoxy-11-oxoundecyl)oxy]phenyl}-10,15,20-triphenylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%		Potassium carbonate (86 mg, 0.650 mmol) was added to a solution ofTPPOH (40 mg, 0.065 mmol) in anhydrous DMF (1.5 mL) at roomtemperature. After the mixture had been stirred for 0.5 h, methyl 11-bromoundecanoate(122 μL, 0.507 mmol) and potassium iodide (106 mg,0.650 mmol) were added in one portion. The reaction mixture wasstirred for 18 h at room temperature under Ar atmosphere. The solventwas removed under reduced pressure. Brine (3 × 30 mL) was added tothe residue and the product was extracted three times with CHCl3 (3 ×30 mL), the organic phase was dried over Na2SO4 and concentrated invacuo. The crude product was purified by column chromatography(silica gel, L x H = 7 cm × 2.4 cm, CHCl3) and from the appropriatefraction precipitation with n-hexane gave porphyrin TPPOCOOMeC11as a purple solid. Yield 43 mg (82%). 1H NMR (500 MHz, 296.9 K,CDCl3): δ = 8.90 (Hpyrr, d, J = 4.5 Hz, 2H), 8.85 (Hpyrr, m, 6H), 8.23 (Ho,d, J = 6.5 Hz, 6H), 8.12 (Ho′ , d, J = 8.5 Hz, 2H), 7.77 (Hm,p, m, 9H), 7.28(Ho′ , d, J = 8.5 Hz, 2H), 4.25 (H4’, t, J = 6.5, 2H), 3.68 (H15’, s, 3H), 2.34(H13’, t, J = 7.5, 2H), 1.98 (H5’, m, 2H), 1.64 (H12’,6′ , m, 4H), 1.47 (H7’,m, 2H), 1.37 (H8’,9′ ,10′ ,11′ , m, 8H), -2.75 (br s, 2H) ppm. 13C NMR (62.9MHz, CDCl3): δ = 174.5 (C14’), 159.2 (C3’), 142.4 (C1’), 135.8 (Co′ ),134.7 (Co), 134.5 (C2’), 131.3 (Cpyrr), 127.8 (Cp), 126.8 (Cm), 120.4 (C5),120.2 (C10,20), 120.1 (C15), 112.9 (Cm′ ), 68.5 (C4’), 51.6 (C15’), 34.3(C13’), 29.74 (C5’), 29.66 (C8’), 29.6 (C9’), 29.5 (C10’), 29.3 (C11’), 26.4(C6’), 25.1 (C12’) ppm. HRMS (MALDI-TOF): calcd. for C56H52N4O3828.4039 [M]+; found 828.4024. FT-IR: 1733.3 cm 1 (vs, -C=O).

Reference： [1]Carbohydrate Polymers,2022,vol. 275

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[ 6287-90-7 ] Synthesis Path-Upstream 1~3

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