[ CAS No. 112-90-3 ]

Name: 112-90-3|(Z)-Octadec-9-en-1-amine|70%
Brand: Ambeed
SKU: A778776
Rating: 90 (32 reviews)

{[proInfo.proName]} ,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

DV 2D 3D

3d Animation Molecule Structure of 112-90-3

Structure of 112-90-3 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Bulk Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 100K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 112-90-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 112-90-3 ]

SDS Specification

Alternatived Products of [ 112-90-3 ]

Product Details of [ 112-90-3 ]

CAS No. :	112-90-3	MDL No. :	MFCD00066507
Formula :	C₁₈H₃₇N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QGLWBTPVKHMVHM-KTKRTIGZSA-N
M.W :	267.49 g/mol	Pubchem ID :	5356789
Synonyms :	1. Oleylamine

Calculated chemistry of [ 112-90-3 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.89
Num. rotatable bonds :	15
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	90.87
TPSA :	26.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	4.75
Log Po/w (XLOGP3) :	3.37
Log Po/w (WLOGP) :	5.98
Log Po/w (MLOGP) :	4.79
Log Po/w (SILICOS-IT) :	6.12
Consensus Log Po/w :	5.0

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.63
Solubility :	0.625 mg/ml ; 0.00234 mol/l
Class :	Soluble
Log S (Ali) :	-3.59
Solubility :	0.068 mg/ml ; 0.000254 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-6.07
Solubility :	0.000227 mg/ml ; 0.000000849 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.17

Safety of [ 112-90-3 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P260-P264-P270-P271-P273-P280-P301+P310-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P314-P363-P391-P403+P233-P405-P501	UN#:	2735
Hazard Statements:	H302-H304-H314-H335-H373-H410	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 112-90-3 ]

* 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 [ 112-90-3 ]
Downstream synthetic route of [ 112-90-3 ]

[ 112-90-3 ] Synthesis Path-Upstream 1~2

1
[ 112-90-3 ]
[ 10010-93-2 ]

Reference： [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 46, p. 14737 - 14742[2] Angew. Chem., 2017, vol. 129, # 46, p. 14932 - 14937,6

2
[ 112-90-3 ]
[ 20154-03-4 ]

Reference： [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 46, p. 14737 - 14742[2] Angew. Chem., 2017, vol. 129, # 46, p. 14932 - 14937,6

[ 112-90-3 ] Synthesis Path-Downstream 1~58

1
[ 112-90-3 ]
[ 112-80-1 ]
(9Z)-N-[(9Z)-9-octadecen-1-yl]-9-octadecenamide [ No CAS ]

Reference： [1]Green Chemistry,2018,vol. 20,p. 375 - 381
[2]Journal of the American Chemical Society,2006,vol. 128,p. 16522 - 16523

2
[ 112-90-3 ]
[ 10305-42-7 ]
N-oleyl-N'-propylsulfamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With triethylamine; In toluene; at 0 - 20℃;	Example 6 - Preparation of lambdaHcis-g-octadecenvD-N'-propylsulfamide, also known as N- oleyl-N'-propylsulfamiotade (6)0 20 g (1 2 mmol) of freshly distilled lambda/-propylsulfamoyl chloride were added dropwise to a solution of the amine and TEA in dry toluene at 0 0C under nitrogen atmosphere The reaction mixture was stirred at room temperature, and the white solid(TEA HCI) was filtered, the solvent was evaporated to dryness and the crude was purified by column chromatography on silica gel with CH2CI2 MeOH/NH3 9 1 , providing the desired product (0 27g) as a white solid Yield 58%, m p 82-83C1H NMR (400 MHz, CDCI3) delta 5 30 (m, 2H, CH=CH), 4 25 (br s, 2H, NH), 2 97 (m, 4H, CH2NHSO2NHCH2), 1 97 (m, 4H, CH2CH=CHCH2), 1 54 (sextet, 2H, J = 7 3 Hz, CH2- <n="19"/>CH3 (Pr)); 1.51 (m, 2H, CH2CH2NHSO2); 1.21 (bm, 22H1 -CH2-); 0.91 (t, 3H, J = 7.3 Hz1 CH2-CH3(Pr)); 0.84 (t, 3H1 J = 6.6 Hz, CH2-CH3 (oleyl)).13C NMR (100 MHz1 CDCI3) delta: 129.9, 129.7 (CH=CH); 44.9 (NHSO2NHCH2 (Pr)); 43.2 (oleyl-CH2NHSO2); 31.8 (CH2-CH2CH3); 29.8-28.9, 26.7 (-CH2-); 27.1 , (CH2-CH=CH- CH2); 22.8 (CH2-CH3 (Pr)); 22.6 (CH2-CH3 (oleyl)); 14.1 (CH3 (oleyl)); 1 1.2 (CH3(Pr)). Anal (C21H44N2SO2) % theor. (% found): C: 64.86 (65.06); H: 11.32 (11.60); N: 7.20 (7.34); S: 8.23 (8.33).

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 389 - 393
[2]Patent: WO2007/85469,2007,A1 .Location in patent: Page/Page column 17-18

3
[ 112-90-3 ]
N-oleylsulfamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With SULFAMIDE; In ethanol; water; for 6.5h;Heating / reflux;	Example 1 - Preparation of lambda/-(cis-9-octadecenyl)sulfamide (1 ), also known as N- oleylsulfamide.To a stirred solution of 0.20 g of sulfamide (2.1 mmol) in 20 ml of H2O under reflux it is added dropwise 0.1 ml (2.1 mmol) of lambda/-oleylamine in 10 ml of EtOH for 30 minutes. The reaction mixture is stirred and refluxed for 6 hours. Then the solvent is evaporated and the white solid is purified in a chromatography column, using CH2CI2:MeOH/NH39.4:0.6 as eluyent; 0.52 g of white solid are obtained. Yield 72%; mp = 68-70 C; 1H NMR (300 MHz, CDCI3) : 5.32 (m, 2H); 4.59 (br s, 2H); 4.38 (br s, 1 H); 3.09 (q, J = 7.0 Hz, 2H); 1.97 (m, 4H); 1.55 (m, 2H); 1.24 (m, 22H); 0.85 (t, J = 6.7 Hz, 3H). 13C NMR (75 MHz, CDCI3) : 129.9; 129.7; 43.6; 31.8; 29.7-26.6; 27.1 ; 27.2; 22.6; 14.1. MS (ES+) [M+HJ+ 347 (100%). Anal. (C18H38N2SO2, 346.57): C, H, N, S.

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 389 - 393
[2]Patent: WO2007/85469,2007,A1 .Location in patent: Page/Page column 16

4
[ 112-90-3 ]
[ 112-82-3 ]
[ 52986-14-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With sodium hydroxide; In methanol; dichloromethane; chloroform;	1-bromohexadecane (15.27 g, 50 mmol) was rapidly added to oleylamine (26.75 g, 100 mmol) at 100 C. The reaction mixture was heated at 120 C. for 30 minutes and than cooled to room temperature. Chloroform(200 ml) was added followed by 1 N NaOH (50 ml). The mixture was then extracted with H2O (200 ml), the organic layer dried (Na2SO4) and concentrated to a syrup. Silica gel column chromatography using 5-20% gradient methanol in dichloromethane afforded 20.5 g of palmityloleylamine as a syrup (yield, 83%). The identity of the product was confirmed using NMR spectroscopy. 1H NMR (CDCl3) d 5.34 (m, 2H, CH=CH), 2.58 (m, 4H), 2.00 (m, 4H), 1.47 (m, 4H), 1.25 (m, 48H), 0.86 (m, 6H). FAB-MS: 493 [M+H]+. (Other reagents could include oleyl-bromide and hexadecane amine)
83%	With sodium hydroxide; In methanol; dichloromethane; chloroform;	Synthesis of palmityloleylamine (1) 1-bromohexadecane (15.27 g, 50 mmol) was rapidly added to oleylamine (26.75 g, 100 mmol) at 100 C. The reaction mixture was heated at 120 C. for 30 minutes and than cooled to room temperature. Chloroform(200 ml) was added followed by 1 N NaOH (50 ml). The mixture was then extracted with H2O (200 ml), the organic layer dried (Na2SO4) and concentrated to a syrup. Silica gel column chromatography using 5-20% gradient methanol in dichloromethane afforded 20.5 g of palmityloleylamine as a syrup (yield, 83%). The identity of the product was confirmed using NMR spectroscopy. 1H NMR (CDCl3) d 5.34 (m, 2H, CH=CH), 2.58 (m, 4H), 2.00 (m, 4H), 1.47 (m, 4H), 1.25 (m, 48H), 0.86 (m, 6H). FAB-MS: 493 [M+H]+. (Other reagents could include oleyl-bromide and hexadecane amine)
83%	at 100 - 120℃; for 0.5h;	N-oleyl-palmityl amine is an important starting material for the compounds according to the present invention. The N-oleyl-palmityl amine can, in principle, be synthesised as described in US 6,395,713. The respective reaction scheme is depicted in Fig. 2. However, the starting material is oleyl amine of technical grade as provided by, e. g., Fluka. An analysis of this starting material by gas chromatography shows a purity of > 70 %, whereby 30 % of the material consist of amine having different chain lengths. The reason for this could be that the material as such is obtained from plant sources. Combining both oleyl amine and 1-bromohexadecane (palmitylbromid) yields N-oleyl-palmityl amine after reacting both starting materials at 100 to 120 C for 30 minutes. The yield is about 83 %.

83%

at 100 - 120℃; for 0.5h;Product distribution / selectivity;

N-oleyl-palmityl amine is an important starting material for the compounds according to the present invention. The N-oleyl-palmityl amine can, in principle, be synthesised as described in US 6,395,713. The respective reaction scheme is depicted in Fig. 2. However, the starting material is oleyl amine of technical grade as provided by, e. g. , Fluka. An analysis of this starting material by gas chromatography shows a purity of No. 70 %, whereby 30 % of the material consist of amine having different chain lengths. The reason for this could be that the material as such is obtained from plant sources. Combining both oleyl amine and 1-bromohexadecane (palmitylbromid) yields N-oleyl-palmityl amine after reacting both starting materials at 100 to 120 C for 30 minutes. The yield is about 83 %.

Reference： [1]Patent: US2003/73640,2003,A1
[2]Patent: US6395713,2002,B1
[3]Patent: WO2006/69782,2006,A2 .Location in patent: Page/Page column 26
[4]Patent: WO2005/105152,2005,A2 .Location in patent: Page/Page column 27; figure 2

5
C₁₆H₁₄O₇ [ No CAS ]
[ 112-90-3 ]
2-(3,4-dihydroxy-phenyl)-N-heptadec-8-enyl-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; In hexane; ethyl acetate; at -20℃; for 193h;	Preparation of 2-(3,4-dihydroxy-phenyl)-N-heptadec-8-enyl-acetamideOverview: Dihydroxyphenylacetic acid was first converted to its anhydride in the presence of DDC (dicyclohexyl carbodiimide). The resulting intermediate was then reacted with oleylamine in the presence of 4-dimethylaminopyridine in DMF.1.5 g of 2,4-dihydroxyphenylacetic acid (1.8 mole) was dissolved in 20 niL of 50:50 v/v ethyl acetate and hexane. Then 1.5 mL of DCC (-1.4 mmole) was added and the reaction continued for 1 hr at room temperature under argon that was bubbled into the solution. A white precipitate of dicyclohexyl urea formed during the reaction. After 3 hr, the urea precipitate was removed and 1.8 mL (5.6 mmol) of oleylamine (C18-content 80-90%; Fisher), was initially dissolved in 10 mL of hexane in the presence of 4-dimethylaminopyridine (0.5 g) and added to the reaction product of the 2,4-dihydroxyphenylacetic acid and DCC. The reaction continued at room temperature for 1 hr and then stored at -20 0C for one week.The resulting mixture was extracted with water followed by 2x with 5 M NaCl and dried under argon. The white pellet was dissolved in 10 mL of CHCl3/MeOH (18:1) and the product isolated by chromatography (silica gel/hexane). 1H NMR data in CD3Cl is provided in Figure 6A.

Reference： [1]Patent: WO2006/86422,2006,A2 .Location in patent: Page/Page column 45

6
[ 112-90-3 ]
[ 96-24-2 ]
3-oleyldithiocarbamoyl-1,2-propanediol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With sodium hydroxide; In CS2; hexane; water;	Thus, CS2 (6.0 ml) was reacted with oleylamine (33.44 grams; 80% pure) in hexane (25 ml), followed by the addition of aqueous NaOH (4.0 grams in 40 ml H2 O) and 3-chloro-1,2-propanediol (11.05 grams). After an aqueous work up, the reaction product obtained was found to be contaminated with a small amount of N-oleylisothiocyanate which was easily separated from the desired diol by column chromatography and elution with 60% ethyl acetate in hexane. The isolated grey waxy 3-oleyldithiocarbamoyl-1,2-propanediol (30.48 grams; 73% yield) was then borated with boric acid (2.26 grams) by the procedure described in Example II above to give the desired compound as a yellow viscous liquid.

Reference： [1]Patent: US5672727,1997,A

7
[ 112-90-3 ]
[ 14227-17-9 ]
[ 135627-22-4 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 7 (Z)-2-(9-Octadecenylamino)-N-(2,4,6-trimethoxyphenyl)acetamide The title compound was prepared according to the procedure for Example 1 by substituting oleyl amine for benzhydryl amine and <strong>[14227-17-9]2,4,6-<strong>[14227-17-9]trimethoxy aniline</strong></strong> for 2,6-diisopropyl aniline. 11.45 g (58%). NMR (CDCl3) delta 0.88 (3H, t), delta 1.2-1.52 (24H, m), delta 2.01 (4H, m), delta 2.71 (2H, t), delta 3.42 (2H, m), delta 3.68 (3H, s), delta 3.79 (6H, s), delta 5.33 (2H, m), delta 6.13, (2H, d), delta 8.31 (1H, bs) IR (film) 3310, 3003, 2928, 1669, 1346, 1062, 954, 811 cm-1.

Reference： [1]Patent: US5153226,1992,A

8
[ 112-90-3 ]
[ 41130-29-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In tert-butyl methyl ether; at 20 - 30℃; for 0.75 - 1h;	To the stirred crude amine solution in TBME (~90 L) pf step 1.3, 6.7 Kg (1.2 eq) (+/-2%) of concentrated (37%) hydrochloric acid are added via dosing pump, over 15-30 minutes, at a temperature of 20-30C (exothermic addition). Approximate volume is 95 L. The clear monophasic solution is stirred for at least 30 minutes at 20-30 C and acetonitrile (225.0 L, 176.85 Kg) (+/-5 %) is charged to the paired reactor. The hydrochloride salt solution is charged to the acetonitrile over 30-60 minutes to form a white precipitate. Approximate volume is 320 L. The precipitate is cooled to 0-6C, hold for at least 1 hour and filtered. The cake volume is about 90 L. The precipitate is washed with 2 x 35 L of chilled acetonitrile and the solid is dried at 25-30C to constant weight (DSC performed). The dried solid is transferred back into the reactor and 10 weight volumes (-135 L, 100 Kg) of TBME are added. The reaction medium is stirred until a solution is obtained. Approximate volume is 150 L. 2 equivalents (~50.5 L) of 2M sodium hydroxide solution in water are added over 15-30 minutes at 15-25C (addition is slightly endothermic). Approximate volume is 200 L and the biphasic mixture is stirred for at least 1 hour at 15-25C and allows separating. The lower aqueous layer is removed and discarded. The organic solution is washed with water (2 x 35L), azeo-dried by distillation at atmospheric (b.p. TBME 58C) and then concentrated to dryness under full house vacuum until residual levels of TBME are within ICH guidelines by headspace GC.

Reference： [1]Patent: EP1746084,2007,A1 .Location in patent: Page/Page column 4-5
[2]Angewandte Chemie - International Edition,2017,vol. 56,p. 8746 - 8750
Angew. Chem.,2017,vol. 129,p. 8872 - 8876,5

9
[ 112-90-3 ]
N-oleylsulfamide [ No CAS ]
N,N'-dioleylsulfamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	With SULFAMIDE; In water; at 20℃; for 48h;Heating / reflux;	Example 13 - Preparation of lambda/,A/'-bis(9-cis-octadecenyl)sulfamide, also known as N, N'- dioleylsulfamide (13).0.68 ml of N-oleylamine (1.4 mmol) are added dropwise to 0.20 g of N- propylsulfamide (1.4 mmol) in 2 ml of water at room temperature. The colourless mixture reaction is stirred under reflux for 48 h, showing an orange colour. The solvent is evaporated and the crude is purified in a chromatography column, using CH2CI2 as eluyent. 0.12 g of white solid (compound 1 ) and 0.26 g of white solid (compound 13) were obtained. Yield (compound 13): 22%; m.p. 85-880C.1H-NMR (400 MHz, CDCI3) delta: 5.32 (m, 4H, CH=CH); 4.25 (bs, 2H, NH); 3.00 (m, 8H,CH2NHSO2); 1.99 (m, 8H, CH2-CH=CH-CH2); 1.53 (sextet, J = 7.3 Hz, 4H, CH2CH3); 1.26 (bm, 44H); 0.87 (t, 3H, J = 7.3 Hz, CH3).13C-NMR (100 MHz, CDCI3) delta: 129.9, 129.7 (CH=CH;; 43.2 (CH2NHSO2); 31.9 (CH2-CH2CH3); 29.7, 29.6, 29.5, 29.4, 29.3, 29.2, 27.2, 26.7 (-CH2); 22.6 (CH2-CH3); 14.0(CH3)

Reference： [1]Patent: WO2007/85469,2007,A1 .Location in patent: Page/Page column 20

10
[ 112-90-3 ]
[ 814-68-6 ]
[ 23586-43-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine; In dichloromethane; at -10 - 0℃; for 4.33333h;	To a solution of oleylamine 78 (26.75 g, 100 mmol) and triethylamine (20 g, 200 mmol) in anhydrous CH2Cl2 (200 mL) at -10 C, a solution of acryloyl chloride (9.9 g, 110 mmol) in CH2Cl2 (100 mL) was added dropwise over a period of 20 min. After the completion of the addition the reaction mixture was stirred for 4 h at 0 C after which the TLC of the reaction mixture showed the completion of the reaction. The reaction mixture was washed with satd. NaHCO3 solution (200 mL), water (200 mL), brine (100 mL) and dried over NaSO4. Concentration of the organic layer provided the product 79 (32 g, 100%) which was used as such in the next step. 1H NMR CDCl3 delta 0.91 (t, J = 6.5Hz, 3H), 1.05-1.35 (m, <n="128"/>24H), 1.42 (t, 2H), 1.96 (m, 4H), 5.31 (t, 1H), 5.33-5.36 (m, 1H), 5.54 (dd, 1H), 6.02 (dd, 1H), 6.18 (dd, 1H), 8.03 (bs, 1H).
	With triethylamine; In dichloromethane;	Example 2Acryloylamido alkane or alkenes: Oleylamine was treated with acryloyl chloride in the presence of TEA in CH2Cl2. After routine work up, the resulted acryloylamido-olean was purified by chromatograph on silica gel (Hexane: ethyl acetate 10:90).

Reference： [1]Patent: WO2008/42973,2008,A2 .Location in patent: Page/Page column 126-127
[2]Patent: WO2008/137470,2008,A1 .Location in patent: Page/Page column 8

11
[ 112-90-3 ]
[ 13076-17-0 ]
[ 1186629-30-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	In N,N-dimethyl-formamide; at 80℃; for 34h;	(300mg, 2.08mmol) L-Lactide was added to a solution of (1.6g, 4.16mmol) of oleyl amine in 10ml DMF. The reaction mixture was heated to 80 0C for (34 hrs). Thorough out this period of time the color turned from colorless to yellow. Reaction was followed by TLC (100% Eth. Ac). When reaction was over, the product was obtained by column chromatography (CHC13/Hexane = 20:80; v/v). Yield = 85%1H-NMR(CDCl3, delta ppm): 0.96(t, 3H) ,1.25-1.39(m, 16H) ,1.43-1.46(d, 3H) ,1.6-1.7(m, 4H) ,2-2.1 (dt, 4H), 3.2(dt, 2H) ,4.2(q, IH) ,5.32-5.35(dt, 2H).

Reference： [1]Patent: WO2009/109973,2009,A2 .Location in patent: Page/Page column 63

12
[ 147962-41-2 ]
[ 112-90-3 ]
N-oleyl-N'-propylsulfamide [ No CAS ]
N,N'-dioleylsulfamide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2009,vol. 44,p. 4889 - 4895

13
[ 112-90-3 ]
[ 175281-76-2 ]
[ 1356856-98-8 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 128 - 131

14
[ 112-90-3 ]
[ 124-30-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium on activated charcoal; In ethanol; at 30℃; under 6000.6 Torr; for 4h;	a) Octadecylamine 2 g of oleylamine in 120 ml of ethanol are hydrogenated at 30 C. under 8 bar of hydrogen in the presence of palladium-on-charcoal. After reacting for 4 h and evaporating the solvent, 1.6 g of product are obtained in the form of a white powder. m/z: ES+ 270.7

Reference： [1]Patent: US8268810,2012,B2 .Location in patent: Page/Page column 42; 44
[2]RSC Advances,2015,vol. 5,p. 16497 - 16500

15
[ 112-90-3 ]
[ 17355-75-8 ]
[ 1428261-48-6 ]

Yield	Reaction Conditions	Operation in experiment
84%		General procedure: To a solution of the corresponding amine (5 equiv) in dry DCM was added a solution of Al(Me)3 in heptane (2 M, 5 equiv) under N2 atmosphere. The mixture was stirred at rt for 1 h. Then, a solution of alkyl carboxylate (1 equiv) in dry DCM was added dropwise. The mixture was refluxed for 14-48 h, and then was carefully poured onto 1 N HCl. The biphasic solution was heated to 40 C for 30 min and cooled to rt. The organic layer was separated, dried over MgSO4 and evaporated. The residue was purified by flash chromatography (eluent n-hexane/EtOAc, 9:1 for pyrazoles and 1:1 for triazoles), except 8b which was recrystallized from hexane.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1708 - 1716

16
[ 741287-00-3 ]
[ 112-90-3 ]
[ 1428261-51-1 ]

Yield	Reaction Conditions	Operation in experiment
68%		General procedure: To a solution of the corresponding amine (5 equiv) in dry DCM was added a solution of Al(Me)3 in heptane (2 M, 5 equiv) under N2 atmosphere. The mixture was stirred at rt for 1 h. Then, a solution of alkyl carboxylate (1 equiv) in dry DCM was added dropwise. The mixture was refluxed for 14-48 h, and then was carefully poured onto 1 N HCl. The biphasic solution was heated to 40 C for 30 min and cooled to rt. The organic layer was separated, dried over MgSO4 and evaporated. The residue was purified by flash chromatography (eluent n-hexane/EtOAc, 9:1 for pyrazoles and 1:1 for triazoles), except 8b which was recrystallized from hexane.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1708 - 1716

17
[ 112-90-3 ]
[ 1134647-60-1 ]
[ 1442019-83-1 ]

Yield	Reaction Conditions	Operation in experiment
53%		General procedure: To a solution of the corresponding amine (5 equiv) in dry DCM was added a solution of Al(Me)3 in heptane (2 M, 5 equiv) under N2 atmosphere. The mixture was stirred at rt for 1 h. Then, a solution of alkyl carboxylate (1 equiv) in dry DCM was added dropwise. The mixture was refluxed for 14-48 h, and then was carefully poured onto 1 N HCl. The biphasic solution was heated to 40 C for 30 min and cooled to rt. The organic layer was separated, dried over MgSO4 and evaporated. The residue was purified by flash chromatography (eluent n-hexane/EtOAc, 9:1 for pyrazoles and 1:1 for triazoles), except 8b which was recrystallized from hexane.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1708 - 1716

18
[ 112-90-3 ]
[ 3173-56-6 ]
[ 1450603-58-3 ]

Yield	Reaction Conditions	Operation in experiment
51%	In N,N-dimethyl acetamide; at 20℃;	General procedure: To a solution of 1i (200mg, 0.75mmol) in dry DMA (3mL) was added benzyl isocyanate (102muL, 0.82mmol). The reaction was stirred at room temperature overnight. Ethyl acetate (80mL) was added and the solution was washed with saturated aq. NaHCO3 (30ml), brine (30ml), and was dried over Na2SO4 and concentrated to dryness. The crude was purified by flash chromatography on silica gel eluting with hexane/EtOAc (4:1) to yield a white solid (152mg, 51%). Mp 74-76; 1H NMR (400MHz, CDCl3) delta 7.23-7.35 (m, 5H), 5.33-5.36 (m, 2H), 4.68 (br s, 1H), 4.36 (s, 3H), 3.14 (t, J=6.8Hz,2H), 1.98-2.03 (m, 4H), 1.43-1.47 (m, 2H), 1.26-1.32 (m, 22H), 0.88 (t, J=6.8Hz, 3H); 13C NMR (CDCl3, 100MHz) delta 158.33, 139.43, 130.26, 130.20, 130.15, 130.07, 129.97, 128.89, 127.70, 44.86, 40.93, 32.13, 30.40, 29.98, 29.76, 29.70, 29.55, 27.45, 27.08, 22.91, 14.32; LCMS, C26H44N2O, [M+H]: 401.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 5188 - 5197

19
[ 112-90-3 ]
[ 120341-33-5 ]
C₄₆H₈₇N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃;	General procedure: Oleylamine (5.35g, 20mmol) was added to the anhydrous dichloromethane solution (200mL) of 4 (10 mmol), 1-Ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDC·HCl, 4.22g, 22mmol), 1-Hydroxybenzotrizole (HOBt, 2.97g, 22mmol) and N,N-Diisopropylethylamine (DIEA, 5.16g, 44mmol) in ice-salt-bath at 0C for 1 h and then at room temperature overnight. The mixture was then washed with saturated aqueous NaHCO3 solution (2×80 mL) and saturated brine (80 mL).The organic phase was dried over Na2SO4, filtered, and concentrated to afford an oil solid, which was further purified by column chromatography on silica gel (EA/PE=1:1, v/v) to yield the synthetic precursor 5a and 5c (Rf = 0.6, EA/PE = 2 : 1, v/v).

Reference： [1]Molecular Pharmaceutics,2016,vol. 13,p. 1809 - 1821
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1771 - 1775

20
[ 112-90-3 ]
[ 1632125-04-2 ]
[ 1632124-88-9 ]

Yield	Reaction Conditions	Operation in experiment
53 mg	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	A solution of 17 (119 mg, 0.23 mmol) in EtOH:1M NaOH (1:1, 3 mL) was stirred for 2 h at r.t. Then, the mixture was neutralized withIRA-120 (H+) resin, filtered and concentrated. The residue thus obtained was dissolved in DMF(2 mL) and oleyl amine (67 mg, 0.25 mmol), DIPEA (118 L, 0.69 mmol) and PyBOP (130 mg,0.25 mmol) were added. After stirring at r.t. overnight, the mixture was evaporated to dryness and the residue was dissolved in CH2Cl2 and washed with 1M HCl, sat. aq. soln. of NaHCO3 and sat. aq. soln. of NaCl. The dried organic phase (MgSO4) was purified by chromatography over silica gel (AcOEt:petroleum ether 1:3) to give 18 as an oil (53 mg, 30%). [alpha]D 29 -1.7 (c 1.05,CH2Cl2); IR (nu cm-1) 3299, 2921, 2852, 1643, 1110, 1092, 823, 738, 701, 614. 1H NMR (300MHz, CDCl3, ppm, J Hz) 7.73-7.67 (m, 4H, H-arom.), 7.42-7.35 (m, 6H, H-arom.), 6.56 (brt, 1H, NH), 5.38-5.32 (m, 2H, CH=CH), 4.62 (dd, 1H, J 6.5, J 4.8, H-3), 4.50 (br dd, 1H, H-4),3.97 (dd, 1H, 2J1?a,1?b 10.0, J1?a,2 7.0, H-1?a), 3.76 (dd, 1H, J1?b,2 5.0, H-1?b), 3.20 (q, 2H, JH,H 6.4,CH2-NH), 2.83 (m, 1H, H-5), 2.70 (m, 1H, H-2), 2.63-2.35 (m, 4H, H-1??a, H-1??b, CH2-N),2.02-1.98 (m, 4H, CH2-CH=CH-CH2), 1.39 (s, 3H, C(CH3)2), 1.48-1.09 (m, 31H, 14CH2,C(CH3)2), 1.05 (s, 9H, C(CH3)3), 0.88 (t, 3H, JH,H 6.3, CH3), 0.83 (t, 3H, JH,H 7.2, CH3). 13CNMR (75.4 MHz, CDCl3, ppm) 171.3 (C=O), 135.7, 135.5, 133.7, 133.5 (C-arom.), 129.9,129.7 (CH=CH), 129.6, 129.5, 127.6, 127.5 (C-arom.), 110.7 (C(CH3)2), 79.2 (C-4), 79.0 (C-3),67.6 (C-2), 63.4 (C-5), 62.5 (C-1?), 49.4 (C-1??), 35.2 (CH2-N), 32.6 (CH2), 31.9 (CH2), 29.7-29.2 (CH2), 27.2, 27.1 (CH2), 26.7 (C(CH3)3), 25.7, 25.0 (C(CH3)2), 22.6 (CH2), 20.6 (CH2), 19.1(C(CH3)3), 14.1, 14.0 (2CH3). CIMS m/z 775 [100%, (M+H)+]. HRCIMS m/z found 775.5804, calc. for C48H79N2O4Si: 775.5809.

Reference： [1]ARKIVOC,2014,vol. 2014,p. 197 - 214

21
[ 112-90-3 ]
[ 81438-31-5 ]
4-(2-hydroxy-3-octadec-8-enylaminopropoxy)chromen-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	In ethanol; at 20℃; for 6h;	General procedure: To a solution of oxiranylmethoxy-chromen-2-one 1 (0.5 g,2.29 mmol) in ethanol was added the appropriate amine (3.43 mmol) and the reaction was stirred at room temperature (except for 10, reaction was performed under refluxing condition) for 4-6 h. The reaction mixture was evaporated under vacuum and the crude product was purified by column chromatography using 3% methanol in chloroform as mobile phase to give desired products 2-11 in excellent yields.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 94,p. 211 - 217

22
[ 112-90-3 ]
[ 24689-27-8 ]
7-(2-hydroxy-3-oleylaminopropoxy)-4-methyl-2H-1-benzopyran-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In ethanol; at 20℃;	General procedure: To a solution of compound 2 (0.30 g, 1.29 mmol) inethanol (10 ml), corresponding amine was added in equimolaramount. The reaction mixture was stirred at room temperaturefor 4-6 h (except for compound 6 and 12: carriedout at 80 C for 8 h). The solvent was removed under reducedpressure and residue was purified by column chromatography (SiO2) using chloroform:methanol (9:1) as eluent toafford the desired compound in excellent yield.

Reference： [1]Medicinal Chemistry,2015,vol. 11,p. 128 - 134

23
[ 112-90-3 ]
[ 79-10-7 ]
(Z)-3-(octadec-9-en-1-ylamino)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63 g	at 40 - 100℃; for 2h;	Example 2 Process for Obtaining the Corrosion Inhibiting Composition Consisting of 3-(octadec-9-enylamino)propanoic acid (2) In a three-necked balloon flask of 500 ml equipped with a magnetic stirrer, a dropping funnel, a thermometer and a condenser were added 50 g (0.187 mol) of oleylamine at a temperature of 40 C. with vigorous stirring slowly added 13.48 g (0.187 mol) of acrylic acid. The reaction is exothermic and the temperature under these conditions rises gradually to 90 C. The reaction mixture was stirred under these conditions for 2 hours and then increased to 100 C. Purification of amino propionic acid was performed using an extraction of the amine did not react with hexane, thus obtaining 63 g of corrosion inhibitor compound with a yield of 92% as a very viscous pale yellow, features spectroscopy are: FTIR (cm-1): 2921, 2854, 1642, 1575, 1463, 1349, 1288, 1209, 1116, 963, 833. 1H NMR (CDCl3), 200 MHz, 8 (ppm): 5.31, 3.02, 2.73, 2.47, 1.98, 1.25, 0.85. 13C NMR (CDCl3), 50 MHz, 8 (ppm): 176.8, 129.9, 129.7, 47.5, 44.8, 40.8, 31.8, 29.7, 29.5, 29.2, 27.2, 22.6 and 14.1.
	With 10H-phenothiazine; In methanol; water; at 30 - 80℃; for 5h;	Step 1: 1 mole of acrylic acid (or 80% acrylic in water) and 0.2 g of phenothiazine (optional) are added into 100 ml methanol (or other alcohol or glycol or glycol ether) and cooled by ice bath and the temperature kept lower than 30 C. To that solution, 1 mole of oleylamine (e.g. as 50 wt % solution) is added drop-wise for 1 hour. After addition it is heated up to 80 C. and kept at 80 C. for 4 hours. Removing methanol by rotary evaporator, N-oleyl-beta-alanine is obtained.

Reference： [1]Patent: US2015/112096,2015,A1 .Location in patent: Paragraph 0051
[2]Patent: US2020/10754,2020,A1 .Location in patent: Paragraph 0082

24
[ 112-90-3 ]
[ 302-79-4 ]
[ 538-75-0 ]
[ 65646-61-9 ]
N-oleylretinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With dmap; In dimethyl sulfoxide; at 25℃;	General procedure: The synthesis of the target compounds was achieved by dissolving a long chain fatty amine (0.011 mol), ATRA (0.011 mol) and DCC (0.011 mol) in DMSO (50 mL). A catalytic amount of DMAP (0.001 mol) was added, and the solution was stirred at room temperature. After completion of the reaction, the reaction mixture was filtered (to remove solid dicyclohexylurea), and the filtrate was dried under reduced pressure. The amidic derivatives 3a and 3b and the acyl urea derivative 4 of ATRA were obtained by column chromatography using gradient elution with hexane and chloroform. The identity of the desired compounds was confirmed using infrared (IR) and 1H and 13C nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry as shown below.

Reference： [1]Molecules,2015,vol. 20,p. 8181 - 8197

25
[ 112-90-3 ]
[ 2419-94-5 ]
C₄₆H₈₇N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 24.5h;Inert atmosphere; Cooling with ice;	Weigh 5.0 g of Boc-Glu-OH, 6.0 g of HOBT, 15.5 g of EDC · HCl In a 100 mL round bottom flask with a branch, Vacuum, filled with nitrogen protection, Add 20 mL of oleylamine, Into 30 mL heavy distilled DCM, stirred to dissolve, Add 33.2 mL of DIEA in ice bath for 0.5 h, Then reacted at room temperature for 24 h. Water pump to remove the solvent, Chloroform was dissolved, washed with saturated NaHCO3 and NaCl, After drying over anhydrous MgSO4 overnight, filtration, solvent removal, Silica gel column chromatography on 200-300 mesh (eluent DCM / EA = 4: 1) gave a white solid Oleylamine-Glu-Boc (Compound 3).

Reference： [1]Journal of Materials Chemistry B,2015,vol. 3,p. 7006 - 7010
[2]Patent: CN104906076,2017,B .Location in patent: Paragraph 0080

26
[ 112-90-3 ]
[ 13726-67-5 ]
C₄₅H₈₅N₃O₄ [ No CAS ]

Reference： [1]Molecular Pharmaceutics,2014,vol. 11,p. 4164 - 4178

27
[ 112-90-3 ]
[ 71942-38-6 ]
(Z)-N-(octadec-9-en-1-yl)-3-oxo-3H-benzo[f]chromene-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 20℃;	General procedure: First of all, 3-oxo-3H-benzo[f]chromene-2-carbonyl chloride (4) was synthesized by the reaction of 3-oxo-3H-benzo[f]chromene-2-carboxylic acid (3, 2.40 g, 10 mmol) with thionyl chloride (2.2 mL,30 mmol) in dry 1,2-dichloroethane (20 mL) at 60-70 C for 4 h. After the removal of excess unreacted thionyl chloride under reduced pressure, the intermediate 4 was obtained and used directly in the next step without further purification. This intermediate 4 (1.29 g, 5 mmol) dissolved in dry dichloromethane (15 mL) was dropwise added to a mixture of a primary amine (6 mmol) and a catalytic amount of triethylamine (0.1 mL). The reaction mixture was stirred at room temperature for 10-30 min before the solvent was removed. The crude was purified by flash silica gel column chromatography to afford the final product 5a-i. Compounds 6a-g were also synthesized using the similar procedures, the only difference being that the primary amines described above were replaced by different aliphatic alcohols.

Reference： [1]Molecules,2015,vol. 20,p. 18565 - 18584

28
[ 112-90-3 ]
[ 13726-67-5 ]
C₄₅H₈₅N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84.7%		General procedure: N-Boc-D-Aspartic acid (5 mmol)25 or N-Boc-D-glutamic acid,26which was prepared according to literature procedure, was dissolvedin CH2Cl2 (50 mL), cooled to 0 C. 1-Hydroxybenzotriazole(HOBt) (1.83 g, 12 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimidehydrochloride (EDCHCl) (2.3 g, 12 mmol) and DIEA(2.58 g, 2 mmol) were gradually added for activation of carboxylicacid. After 0.5 h stirring, oleyl amine (3.57 g, 90%, 12 mmol) wasadded, and resulting mixture was stirred at room temperatureovernight. The solvent was then removed under reduced pressure.EtOAc was added to dissolve the residue, and the solution waswashed with water, saturated aqueous NaHCO3 solution and saturatedbrine. The organic layer was dried over anhydrous sodiumsulfate and concentrated to give a white solid. The crude productwas purified by silica gel column chromatography (PE/EA = 1/1,v/v).

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 5756 - 5763
[2]RSC Advances,2017,vol. 7,p. 8823 - 8831

29
[ 112-90-3 ]
[ 34404-28-9 ]
C₄₆H₈₇N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68.4%		General procedure: N-Boc-D-Aspartic acid (5 mmol)25 or N-Boc-D-glutamic acid,26which was prepared according to literature procedure, was dissolvedin CH2Cl2 (50 mL), cooled to 0 C. 1-Hydroxybenzotriazole(HOBt) (1.83 g, 12 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimidehydrochloride (EDCHCl) (2.3 g, 12 mmol) and DIEA(2.58 g, 2 mmol) were gradually added for activation of carboxylicacid. After 0.5 h stirring, oleyl amine (3.57 g, 90%, 12 mmol) wasadded, and resulting mixture was stirred at room temperatureovernight. The solvent was then removed under reduced pressure.EtOAc was added to dissolve the residue, and the solution waswashed with water, saturated aqueous NaHCO3 solution and saturatedbrine. The organic layer was dried over anhydrous sodiumsulfate and concentrated to give a white solid. The crude productwas purified by silica gel column chromatography (PE/EA = 1/1,v/v).

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 5756 - 5763
[2]RSC Advances,2017,vol. 7,p. 8823 - 8831

30
[ 112-90-3 ]
[ 112-80-1 ]
[ 125238-99-5 ]
[ 207857-15-6 ]
N-(4-guanidino-1-oxo-1-(octadecylamino)butan-2-yl)octadec-9-enamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.2 g		Example 20 Preparation of C18(oleic)-norArg-C18 N-(4-guanidino-1-oxo-1-(octadecylamino)butan-2-yl)octadec-9-enamide (0607) Fmoc-Dab(Boc)-resin. To 5 g of 2-chlorotrityl chloride resin with 1.3 mmol/g substitution (Novabiochem, 01-64-0114) in 50 ml of dry DCM in 60 ml reaction vessel for solid phase synthesis, 5.726 g (13 mmol, 2 eq) of Fmoc-Dab(Boc)-OH (Mw=440.5, (Fmoc-(N-gamma-Boc)-L-alpha,gamma-diaminobutyric acid, AnaSpec, 28246) and 2.26 ml (13 mmol, 2.0 eq) of DIPEA (Aldrich, Mw=129.2, d=0.74) were added. (0608) Dab(Boc)-resin. After 3 hrs the resin was washed 3× with DCM/MeOH/DIPEA (17:2:1), 3×DCM, 2×DMF, 3×DCM and Fmoc group was deprotected with 50 ml of 20percent piperidine/DMF twice for 15 min. (0609) C18:1-Dab(Boc)-resin. After Fmoc deprotection the resin was washed with 3×DCM, 2×MeOH and 3×DCM and for the coupling reaction 3.7 g (13 mmol) of oleic acid (Sigma, Mw=282.47, d=0.891), 5.37 g (13 mmol) of HCTU (Mw=413.7) and 2.62 ml (13 mmol) of DIPEA (Mw=129.2, d=0.74) in 50 ml of DMF were added. (0610) After 1 hr of reaction the resin was washed with 3×DCM, 2×MeOH and 3×DCM and progress of reaction was checked by Kaiser test which was negative (no free amine groups present). (0611) C18:1-Dab(Boc)-OH (Mw=566.56) was cleaved from the resin by 1percent TFA/DCM (5×50 ml for 2 min was filtered to flask with 2 ml 10percent pyridine/MeOH) and solvent was evaporated. (0612) C18:1-Dab(Boc)-C18:1 (Mw=734.95). Second coupling was carried out in solution. To the oily residue from the previous reaction, 3.725 g (9.75 mmol) of oleyl amine (Sigma, Mw=267.49, 70percent), 4.033 g (9.75 mmol) of HCTU (Mw=413.7) and 1.69 ml (9.75 mmol) of DIPEA (Mw=129.2, d=0.74) in 50 ml of DMF were added. After 4 hr 100 ml of AcOEt was added and organic layer was washed in separatory funnel with 3×0.5 M HCl, 3×10percent NaCO3 and 3×NaCl. AcOEt layer was dried with anhydrous MgSO4 and evaporated. (0613) C18:1-Dab-C18 (Mw=635.9). To the oily residue from the previous reaction, 100 ml of 80percent TFA/DCM 2.5percent TIS was added and after 20 min solvent was evaporated. (0614) C18:1-norArg(diBoc)-C18:1 (Mw=874.13). The residue was dissolved in 50 ml of DCM and pH was adjusted to 9 with TEA. 2.348 g (6 mM, 1 eq) of 1,3-Di-Boc-2-(trifluoromethylsulfonyl)guanidine (Mw=391.36, Aldrich 15033) was added and after 4 hrs DCM was evaporated. (0615) C18:1-norArg-C18:1 (Mw=674.1) To the oily residue from the previous reaction 100 ml of 95percent TFA/DCM 2.5percent TIS was added and after 3 hrs solvent was evaporated. Crude product was purified on TELEDYNE Isco CombiFlash Rf instrument using 48 g normal phase silica gel column, 100percent DCM for 3 CV (column volume) and 0-20percent MeOH for 10 CV, detection 214 nm, flow 45 ml/min. DCM/MeOH was evaporated and residue was precipitated by 0.1M HCl. Yield: 3.2 g.

Reference： [1]Patent: US9339461,2016,B2 .Location in patent: Page/Page column 86-87

31
[ 10323-20-3 ]
[ 112-90-3 ]
N,N-bis(d-arabinityl)-oleylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium cyanoborohydride; toluene-4-sulfonic acid; In methanol; at 50℃; for 24h;	Oleylamine (0.22mL, 178mg, 0.660mmol) was added to a mixture of MeOH (8mL) and p-TsOH (92mg, 0.48mmol). d-Arabinose (727mg, 4.84mmol) and NaCNBH3 (247mg, 3.94mmol) were then added and the mixture was stirred (50C, 24h). The reaction was then recrystallised in MeOH. The precipitate was concentrated, HCl (25mL acetyl chloride in MeOH, 5%, v/v) was added twice with further concentrated. The reaction mixture was then purified via column chromatography (DCM/MeOH/EtOH/NH3, 90:4:4:2 to 75:10:10:5) to give amine 1s as a white crystalline solid (275mg, 0.514mmol, 78%). Mp=248.9-250.4C; Rf=0.42 (DCM/MeOH/EtOH/NH3, 5:2:2:1, v/v); [alpha]D21=+10 (c0.1, MeOH); IR (film) 3317, 2922, 2853, 1404, 1025, 546cm-1; 1H NMR (500MHz, D2O): delta 5.39-5.33 (m, 2H, H-9?-H-10?), 4.36 (d, J4,3=8.6Hz, 2H, H-4), 3.87 (d, J1a,1b=10.5Hz, 2H, H-1a), 3.79-3.74 (m, 2H, H-3), 3.70 (dd, J1b,1a=11.5Hz, J1b,2=4.5Hz, 2H, H-1b), 3.54 (d, J2,3=8.7Hz, 2H, H-2), 3.49-3.47 (m, 2H, H-5a), 3.39 (d, J5b,5a=11.9Hz, 2H, H-5b), 2.04-2.01 (m, 4H, H-8? and H-11?), 1.81-1.78 (m, 2H, H-1?), 1.36-1.28 (m, 24H, H-2?-H7?, H-12?-H-17?), 0.90 (t, J18?,17?=6.0Hz, 3H, H-18?); 13C NMR (75MHz, D2O) 129.4 (C-9?-C-10?), 71.6 (C-2), 71.2 (C-3), 64.4 (C-4), 63.2 (C-1), 54.6 (C-5), 26.8 (C-8?-C-11?), 26.1 (C-1?), 22.3 (C-2?-C-7?, C-12?-C17?), 13.0 (C-18?); HRMS(ESI) m/z calcd for [C28H57NO8+H]+: 536.4157, obsd: 536.4172

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 3932 - 3939

32
[ 112-90-3 ]
[ 7710-20-5 ]
1,2,4,5-benzenetetracarboxylic acid tetraoleylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	In chloroform; at 40℃; for 4h;Inert atmosphere;	Synthesis Example 5 Synthesis of Thickening/Stabilizing Agent (5) (1,2,4,5-benzenetetracarboxylic acid tetraoleylamide) Into a 100-mL four-neck separable flask equipped with a Dimroth condenser, a nitrogen inlet, a dropping funnel, and a thermocouple, 20 mL of chloroform and 9.8 g (0.036 mol) of oleylamine were charged. The system internal temperature was set at 40 C. Subsequently a solution of 3 g (0.009 mol) of pyromellitic acid tetrachloride in 10 mL of chloroform was added dropwise over 2 hours, followed by aging for further 2 hours. The crude mixture, from which low-boiling components were removed on an evaporator, was washed with methanol and yielded a white wet powder. Further, the obtained wet powder was recrystallized from CHCl3/CH3OH (70/30 (v/v)) and yielded 6.4 g of 1,2,4,5-benzenetetracarboxylic acid tetraoleylamide in a yield of 56%. The reaction product was identified in structure by 1H-NMR. 1H-NMR (270 MHz, CDCl3): delta 0.81-0.95 (m, 12H), 1.03-1.85 (m, 88H), 1.96-2.04 (m, 8H), 3.12-3.40 (m, 4H), 5.35-5.56 (m, 8H), 8.7-9.1 (m, 2H)

Reference： [1]Patent: US2016/310384,2016,A1 .Location in patent: Paragraph 0092-0095

33
[ 112-90-3 ]
C₁₈H₂₀O₁₀ [ No CAS ]
N-oleylcaffeamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With dmap; In dichloromethane; at 20℃; for 6h;	Ethyl chloroformate (1.52 mL, 16.7 mmol) and TEA (2.2 mL, 16 mmol) were added to a suspension of caffeic acid (0.737 g, 3.8 mmol) in DCM (10 mL) and stirred for 1 h at -15 C until TLC analysis revealed a total consumption of starting material. Oleyl amine (17.4 mL, 80 mmol) and DMAP (0.030 g, 0.08 mmol) were then added and the mixture stirred at room temperature for 6 h. On completion, the solvent was evaporated in vacuo, and the crude product purified by Sephadex LH 20 with MeOH as eluent to give N-oleylcaffeamide (18f).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 130,p. 248 - 260

34
[ 112-90-3 ]
(S)-4-(oxiranylmethoxy)-2H-chromen-2-one [ No CAS ]
(S)-4-[2-hydroxy-3-(octadec-9-en-1-ylamino)propoxy]-2H-chromen-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	In ethanol; at 20℃; for 6h;	(S)-18 was obtained from 4-hydroxycoumarin 2 (0.5 g, 3.08 mmol) and (R)-(-)-epichlorohydrin (1.14 g, 12.34 mmol) by the applying the same procedure as for the racemic compound. 20 Epoxide (S)-18 (0.5 g 2.24 mmol) on reaction with oleyl amine (0.52 g, 2.75 mmol) in ethanol at room temperature resulted in the formation of enantiopure coumarinyl amino alcohol (S)-10, which was purified by column chromatography on silica gel using chloroform/methanol (97:3) as eluent. Off white semi solid; Yield: 71%.

Reference： [1]Tetrahedron Asymmetry,2017,vol. 28,p. 734 - 743

35
[ 112-90-3 ]
(R)-4-(oxiranylmethoxy)-2H-chromen-2-one [ No CAS ]
(R)-4-[2-hydroxy-3-(octadec-9-en-1-ylamino)propoxy]-2H-chromen-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	In ethanol; at 20℃; for 6h;	General procedure: (S)-18 was obtained from 4-hydroxycoumarin 2 (0.5 g, 3.08 mmol) and (R)-(-)-epichlorohydrin (1.14 g, 12.34 mmol) by the applying the same procedure as for the racemic compound. 20 Epoxide (S)-18 (0.5 g 2.24 mmol) on reaction with oleyl amine (0.52 g, 2.75 mmol) in ethanol at room temperature resulted in the formation of enantiopure coumarinyl amino alcohol (S)-10, which was purified by column chromatography on silica gel using chloroform/methanol (97:3) as eluent. Off white semi solid; Yield: 71%. An analogous method was applied for the synthesis of enantiopure (R)-10 using and (S)-(+)-epichlorohydrin. Off white semi solid; Yield: 68%.

Reference： [1]Tetrahedron Asymmetry,2017,vol. 28,p. 734 - 743

36
[ 112-90-3 ]
[ 2483-46-7 ]
C₃₄H₆₅N₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃;	General procedure: Step 2: Oleylamine (1.2 equiv.) was added to the anhydrous dichloromethane solution of the product obtained in last step (1 equiv.), HOBt (1.2 equiv.), EDCI (1.2 equiv.) and DIEA (2 equiv.) in ice-salt-bath at 0C. The mixture was stirred at 0C for 1h and then at room temperature overnight. The reaction solution was washed with saturated aqueous NaHCO3 solution (2×50mL) and brine (50mL). The organic solvent was dried over Na2SO4, filtered, and concentrated to afford an oil solid, which was further purified by column chromatography on silica gel (EA/PE=1/2, v/v) to yield pure compound 1 (85%) or 2 (66%).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 136,p. 585 - 595

37
[ 112-90-3 ]
[ 77958-57-7 ]
C₁₅₀H₂₅₂N₉O₆P₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		Step 2: In a 150 mL round bottom flask, 4 g of HCCP-PHBA was weighed and 60 mL of tetrahydrofuran was added and stirred. 7.46 g of oleylamine was added and 40 mL of tetrahydrofuran was added. After dissolving, it was added dropwise to a solution of HCCP-PHBA in tetrahydrofuran. Stirring the reaction for 6h; then adding 2g sodium borohydride and 10mL anhydrous methanol, stirring reaction for 12h; the product steamed to remove the solvent, add deionized water after washing and then liquid separation, take the upper oil phase; then add ethanol washing, static The purified product was dried in a vacuum oven for 12 hours to obtain a star compound (HCCP-OA) in a yield of 80%.

Reference： [1]Patent: CN106565786,2017,A .Location in patent: Paragraph 0024; 0036

38
[ 112-90-3 ]
[ 112-80-1 ]
[ 125238-99-5 ]
[ 207857-15-6 ]
N-(4-guanidino-1-((Z)-octadec-9-en-1-ylamino)-1-oxobutan-2-yl)oleamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		C18:1-norArg-C18:1 was synthesized as follows. Fmoc-N gamma-Boc-L-2,3-diaminobutyric acid was dissolved in dichloromethane (DCM), 2eq of diisopropylethyl amine (DIPEA) and the resulting solution was added to 2-chlorotrityl choride resin. After one hour, the resin was washed with DCM and Fmoc group was removed by treatment with 20percent piperidine in DMF yielding the free alpha-amine. Oleic acid was preactivated with 2-(6-Chloro-1H-benzotriazole-1-yl)-1,1,3,3-tetramethylaminium hexafluorophosphate (HCTU) and 2 equivalents of DIPEA and added to the resin and the reaction was deemed complete by negative Kaiser test. The lipidated compound was cleaved from the resin by multiple treatments with 1percent trifluoroacetic acid (TFA) in dichloromethane followed by evaporation under reduced pressure yielding free carboxylate intermediate. The second alkyl chain was attached by preactivating the free carboxyl group with (1-Ethyl-3-(3-dimethyllaminopropyl)-carbodiimide hydrochloride) (EDC) and N-Hydroxybenzotriazole (HOBt) in a 1:1 mixture of DMF and DCM for 10 minutes followed by addition of oleyl amine in same solvent and subsequent stirring for 30 minutes. Crude compound was purified by flash chromatography (Hexane/AcOEt gradient). The pure dialkylated intermediate was dissolved in 1M HCl/ethyl acetate solution and the Boc group was removed within one hour followed by removal of the solvent under reduced pressure. The resulting white solid was taken up in DCM to which was added TEA facilitate dissolution followed by treatment with 1, 3 Di-Boc-2-(trifluoromethylsulfonyl) guanidine for one hour. Upon completion of the reaction DCM was washed with 2 M sodium bisulfate, saturated sodium bicarbonate and dried over MgSO4 and removed under reduced pressure. The resulting residue was dissolved in absolute ethanol and two Boc groups were removed by adding dissolved compound drop wise to 12N HCl. Final product precipitated during reaction and was crystallized from EtOH.

Reference： [1]Patent: US2017/216227,2017,A1 .Location in patent: Paragraph 0339

39
[ 112-90-3 ]
3-devinyl-3<SUP>1</SUP>-methoxymethyl-13<SUP>2</SUP>-demethoxycarbonylpheophorbide-a [ No CAS ]
C₅₁H₇₁N₅O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;Sealed tube;	Chlorin 15 (32.8 mg, 0.059 mmol) in anhydrous DMF (800 mul) was added to HBTU activating agent (47.2 mg, 0.125 mmol), DIPEA (20 muL) and olelyamine (19.0 mg, 23.5muL, 0.071 mmol). After stirring at room temperature overnight in a closed vial, the reaction mixture was extracted with 2:1 CHCl3:MeOH and Dl H2O five times. The combined organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by diol silica gel chromatography (gradient; DCM/MeOH = 97/3). The compound identity was confirmed by UPLC and mass spectrometry (C8 sunfire column, 0.6 mL/min flow at 60 C with a gradual solvent gradient, 0.1% formic acid in water/acetonitrile 60/40 to 0/100 for three min with a hold at the same ratio for another 1 min and then gradually changed back to 60/40 over the last 1 min. Product eluted at 4.015 min. ESI+MS m/z calculated for C51H71N5O3 [M+H]+ 802, found 803. See Figure 13.

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 8125 - 8129
Angew. Chem.,2018,vol. 130,p. 8257 - 8261,5
[2]Patent: WO2017/156616,2017,A1 .Location in patent: Page/Page column 23; 26

40
[ 112-90-3 ]
3-Formyl-3-deethylphytochlorin methyl [ No CAS ]
C₅₀H₆₇N₅O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;Sealed tube;	Chlorin 7 in anhydrous DMF (800 mul) was added to HBTU activating agent (2.5 mol equivalents), DIPEA (<3% v/v) and olelyamine (1 mol equivalent). After stirring at room temperature overnight in a closed vial, the reaction mixture was extracted with 2:1 CHCl3:MeOH and Dl H2O five times. The combined organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The compound identity was confirmed by UPLC and mass spectrometry (C8 sunfire column, 0.6 mL/min flow at 60 C with a gradual solvent gradient, 0.1 % formic acid in water/acetonitrile = 60/40 to 0/100 for three min with a hold at the same ratio for another 1 min and then gradually changed back to 60/40 over the last 1 min. Product eluted at 4.130 min. ESI+MS m/z calculated for C50H67N5O3 [M+H]+ 786, found 787.

41
[ 112-90-3 ]
[ 24533-72-0 ]
C₅₁H₆₉N₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;Sealed tube;	Pyropheophorbide-a (2) (30.0 mg, 0.056 mmol) in anhydrous DMF (800 pL) was added to HBTU activating agent (25.5 mg, 0.118 mmol, 1.2 mol eq.), olelyamine (19.0mg, 23.5 muL, 0.071 mmol, 1.2 mol eq.) and DIPEA (20 muL) for basic conditions. After stirring at room temperature overnight in a closed vial, the reaction mixture was extracted with 2:1 CHCl3:MeOH and washed with Dl H2O five times. The combined organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The compound identity was confirmed by UPLC and mass spectrometry (C8 sunfire column, 0.6 mL/min flow at 60 C with a gradual solvent gradient, 0.1% formic acid in water/acetonitrile = 60/40 to 0/100 for three mm with a hold at the same ratio for another 1 mm and then gradually changed back to 60/40 over the last 1 min. Product eluted at 4.406 min. ESI+MS mlz calcd for C51H69N5O2 [M+H]+786, found 785. See Figure 11.

42
[ 112-90-3 ]
C₁₅H₁₂F₉N₆P [ No CAS ]
C₅₄H₁₀₈N₃P [ No CAS ]
[ 10010-93-2 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 14737 - 14742
Angew. Chem.,2017,vol. 129,p. 14932 - 14937,6

43
[ 112-90-3 ]
[ 4534-73-0 ]
1,2,3,4-butanetetracarboxylic acid tetraoleylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%		Into a 100-mL four-neck separable flask equipped with a Dimroth condenser, a nitrogen inlet, a dropping funnel, and a thermocouple, 20 mL of pyridine, 4.2 g (0.021 mol) of 1,2,3,4-butanetetracarboxylic acid-1,2:3,4-dianhydride, and 11.3 g (0.042 mol) of oleylamine were charged, followed by aging for 3 hours at a set system internal temperature of 50 C. Subsequently 5.4 g (0.042 mol) of 2-ethylhexylamine and 5.8 g (0.048 mol) of diisopropylcarbodiimide were charged, followed by aging for further 8 hours to give a crude mixture. After removing low-boiling components on an evaporator therefrom, the crude mixture was washed with methanol and yielded a pale yellow wet powder. The obtained wet powder was subjected to recrystallization from CHCl3/CH3OH (70/30 (v/v)) and yielded 16.7 g of 1,2,3,4-butanetetracarboxylic acid di(2-ethylhexylamide)di(oleylamide) (a mixture of 1,2,3,4-butanetetracarboxylic acid-1,4-di(2-ethylhexylamide)-2,3-di(oleylamide) and 1,2,3,4-butanetetracarboxylic acid-1,3-di(2-ethylhexylamide)-2,4-di(oleylamide)) in a yield of 83%. The structure of the reaction product was identified by 1H-NMR. 1H-NMR (270 MHz, CDCl3): delta 0.81-0.88 (m, 18H), 1.0-1.4 (m, 70H), 1.40-1.45 (m, 8H), 1.81-1.99 (m, 8H), 2.90-3.45 (m, 6H), 5.32-5.40 (m, 4H), 6.32 (m, 4H). A procedure similar to that in Example 1 was performed, except for using 11.3 g (0.042 mol) of oleylamine instead of 5.4 g (0.042 mol) of 2-ethylhexylamine, and yielded 20.9 g of 1,2,3,4-butanetetracarboxylic acid tetraoleylamide in a yield of 81%. The structure of the reaction product was identified by 1H-NMR. 1H-NMR (270 MHz, CDCl3): delta 0.81-0.88 (m, 12H), 1.0-1.4 (m, 104H), 1.40-1.45 (m, 8H), 1.81-1.99 (m, 8H), 2.90-3.45 (m, 6H), 5.32-5.40 (m, 8H), 6.32 (m, 4H)

Reference： [1]Patent: US2017/320814,2017,A1 .Location in patent: Paragraph 0074-0079

44
[ 525-76-8 ]
[ 112-90-3 ]
(Z)-2-methyl-3-(octadec-9-en-1-yl)quinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85.65%		General procedure: 2-Methyl-4H-3,1-benzoxazin-4-one, 7 (3.00g, 18.60 mmol) was dissolved in 10 ml of ethanol ina 250 ml round bottom ask and the reaction mixturewas allowed to stir for 5 mins. at room temperature forcomplete dissolution, followed by the addition of thecorresponding amino containing compounds (18.60mmol). The mixture was then heated under reux forthe required number of periods as determined by the TLC monitoring. The reaction mixture was allowedto cool, fltered by suction and air-dried to affordmoderate to excellent yields of various 2-methyl-3-substituted quinazolin-4(3H)-one derivatives, 8a-q.

Reference： [1]Oriental Journal of Chemistry,2017,vol. 33,p. 562 - 574

45
[ 571-60-8 ]
[ 112-90-3 ]
(Z)-2-(octadec-9-en-1-ylamino)naphthalene-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With cerium(III) chloride heptahydrate; triethylamine; In ethanol; at 20℃; for 4h;	General procedure: The following procedure is the generalized synthetic procedure used for the synthesis of 2-amino-substituted-1,4-naphthoquinone derivatives. To the mixture of 1,4-dihydroxy naphthalene (100 mg, 0.62 mmol), amine (0.75 mmol), and CeCl3*7H2O (20 mg, 0.062 mmol) in 10 mL ethanol, TEA (1.25 mmol) was added at room temperature. The reaction mixture was stirred for 4 h at room temperature. After the reaction was confirmed as completed by TLC (DCM: MeOH = 19: 1), 10 mL cold water was added to the reaction solution. The resulting precipitate was filtered and washed with 20 mL EtOH. The desired 1,4-naphthoquinone derivatives were obtained as a solid compound.
30%	With cerium(III) chloride heptahydrate; triethylamine; In ethanol; at 20℃; for 6h;	1,4-Dihydroxy naphthalene (100mg, 0.624mmol )was dissolved in 10mL CeCl EtOH37H2O (20mg, 0.062mmol), Oleylamine (200mg, 0.7488mmol) and TEA (130mg, 1.25mmol) in turn, to slowly It was added dropwise and reacted at room temperature.After 6 hours check the reaction completion (EA: HEX = 1: 4 check with TLC) and then, after water quenched and extracted with DCM, and anhydrous MgSO4was dried and concentrated under reduced pressure and filtered.The obtained residue was purified by silica column chromatography (developing solvent HEX -> EA: HEX = 1 :up to 6) to give the desired compound 5 was obtained (yield: 30%).

Reference： [1]Bulletin of the Korean Chemical Society,2017,vol. 38,p. 1411 - 1414
[2]Patent: KR2018/11949,2018,A .Location in patent: Paragraph 0159-0162

46
[ 112-90-3 ]
N^α-Z-N^ε-Boc-D-Lys-OSu [ No CAS ]
5-benzyl 1-tert-butyl (6-(octadec-9-en-1-ylamino)-6-oxohexane-1,5-diyl)(R,Z)-dicarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With sodium hydrogencarbonate; In 1,4-dioxane; water; at 20℃;Sealed tube;	General procedure: In a 30 mL sealed cap glass vial, 2,3-bis(tetradecyloxy)propan-l-amine hydrochloride (260 mg, 0.5 mmol) was suspended in 1:2 satd. aq. sodium bicarbonate/dioxane (21 mL) and treated with Boc-L-Tyr(0-Bn)-OSu (234 mg, 0.5 mmol), and the resulting mixture was stirred at rt overnight. The mixture was diluted with water and brine, and extracted with ethyl acetate (2 x 25 mL). The combined organic layers were dried over sodium sulfate, and evaporated. The residue was purified by silica gel column (hexane-ethyl acetate (0-100%)) to give the title compound as a white solid (205 mg, 49% yield).

Reference： [1]Patent: WO2018/26866,2018,A1 .Location in patent: Paragraph 0159; 0231

47
[ 112-90-3 ]
C₁₄H₁₆Cl₂O₇ [ No CAS ]
C₃₁H₄₉Cl₂NO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%		To a 1L four-necked flask equipped with a mechanical stirrer and a thermometer was added 2,4-(3,4-dichlorobenzylidene)-methyl-D-gluconate (II-1) 47.1 g at 20-25C. (128.27 mmol), 300 mL of ethanol, 0.06 g (0.0492 mmol) of catalyst 4-dimethylaminopyridine (DMAP), and after stirring for 30 min, 102.9 g (384.82 mmol) of oleylamine (III) was added and stirred overnight at room temperature. After the reaction was completed, 100 mL of water was added to the system, and the mixture was stirred and filtered for 2 hours. The filter cake was washed with water, washed with methanol and sucked dry to give a crude product. The crude product was recrystallized from methanol and dried to give 50.2 g of product with a yield of 65%

Reference： [1]Patent: CN107573319,2018,A .Location in patent: Paragraph 0046; 0047; 0048; 0049

48
[ 112-90-3 ]
cinnamoyl-L-threonine [ No CAS ]
(2S,3R)-2-cinnamamido-3-hydroxy-N-(oleyl)butanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 12h;	General procedure: Fatty acid or Aromatic acid (3a-3s, 10.25 mmol) was dissolved in ice-cold anhydrous dichloromethane (40 mL) and to this oleyl amine (12.3 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC.HCl, 12.3 mmol) and hydroxy benzotriazole (HOBt, 15.38 mmol) were added successively at 0 C and the mixture was stirred for 12 h at room temperature. The reaction was monitored using micro TLC (hexane: ethyl acetate, 35:65, v/v). At the end of the reaction, the mixture was dissolved in 75 mL of CHCl3, which was then washed by 5% NaHCO3 solution, saturated NaCl solution successively. The chloroform layer was dried with anhydrous Na2SO4 and the filtrate was dried under reduced pressure. The crude mixture was purified by silica gel chromatography, the title compounds were obtained with 75-80% yield.