[ CAS No. 170572-38-0 ] {[proInfo.proName]}

Name: 170572-38-0|2,5,8,11,14,17,20-Heptaoxadocosan-22-amine|98%
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 170572-38-0 ]

CAS No. :	170572-38-0	MDL No. :	MFCD13184965
Formula :	C₁₅H₃₃NO₇	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IQQSLHPGFFGOJW-UHFFFAOYSA-N
M.W :	339.43	Pubchem ID :	18764651
Synonyms :		Chemical Name :	2,5,8,11,14,17,20-Heptaoxadocosan-22-amine

Safety of [ 170572-38-0 ]

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

Application In Synthesis of [ 170572-38-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 170572-38-0 ]

[ 170572-38-0 ] Synthesis Path-Downstream 1~40

1
[ 23911-26-4 ]
[ 170572-38-0 ]
6,9-bis(carboxymethyl)-3-(2-oxo-6,9,12,15,18,21,24-heptaoxa-3-azapentacosyl)-11-oxo-15,18,21,24,27,30,33-heptaoxa-3,6,9,12-tetraazatetratriacontanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	In DMF (N,N-dimethyl-formamide) at 20℃; for 2h;

Reference： [1]Current Patent Assignee: BRACCO SPA - US6342598, 2002, B1 Location in patent: Page column 30

2
[ 170572-38-0 ]
[ 10436-25-6 ]
11-[[(1,1-dimethylethoxy)carbonyl]amino]-N-(3,6,9,12,15,18,21-heptaoxadocosyl)undecanamide [ No CAS ]

Reference： [1]Patent: US6342598,2002,B1 .Location in patent: Page column 34

3
[ 170572-38-0 ]
[ 4759-48-2 ]
[ 854601-59-5 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; dicyclohexyl-carbodiimide In benzene at 20℃;	2 SYNTHESIS OF CH3-(OCH2CH2)7-NH-13-CIS-RETINAMIDE (PEG7-13-cis-RA) 0.2257 grams of CH3(OCH2CH2)7-NH2 (0.6656 mmoles), 0.044 grams of 1-hydroxybenzyltriazole (0.3328 mmoles), and 0.200 grams of 13-cis-retinoic acid (0.6656 mmoles) were dissolved in 10 mL of benzene. To this solution was added 0.192 g 1,3-dicyclohexylcarbodiimide (0.9318 mmoles) and the resulting reaction mixture was stirred overnight at room temperature. The reaction mixture was filtered, the solvent removed using rotary evaporation, and the product dried under vacuum. The product was dissolved in 20 mL dichloromethane and the solution was washed twice with 15 mL deionized water. The organic phase was dried over Na2SO4, filtered, and the solvent removed using rotary evaporation. To the recovered product was added 2 drops of dichloromethane containing 50 ppm butylated hydroxytoluene, and the product was dried under vacuum. Yield 0.426 g. 1H NMR (DMSO): δ 1.01 (s, 2 CH3), 1.68 (s, CH3), 3.5 (br m, PEG), 6.20 (m, 3H).

Reference： [1]Current Patent Assignee: NEKTAR THERAPEUTICS - US2005/136031, 2005, A1 Location in patent: Page/Page column 19

Yield	Reaction Conditions	Operation in experiment
56%		3.B B B 3,6,9,12,15,18,21-heptaoxadocosylamine 9.2 g of compound A), 4-nitrobenzenesulfonic acid 3,6,9,12,15,18,21-heptaoxadocos-1ester (0.0175 mol), are diluted in NH40H at 60° C. in 10 minutes. After 2.5 h at 60° C., the solution is cooled and the NH4 OH excess is evaporated, the crude is diluted in 70 mL of H2 O and percolated on a cation exchange resin DuoliteR C20MB. The elude is concentrated under reduced pressure and the crude is purified by means of flash chromatography. 3,3 g of 3,6,9,12,15,18,21-heptaoxadocosylamine (0.0098 mol) are obtained. Yield: 56%

5
[ 170572-38-0 ]
[ 70972-98-4 ]
C₃₁H₅₅NO₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In [D₃]acetonitrile at 24.84℃;
317 mg	With magnesium sulfate In dichloromethane at 20℃; for 24h; Inert atmosphere; Schlenk technique;	Synthesis of imines 3a, 3b MgSO4 (106 mg, 0.88 mmol, 1.50 eq.) was added to a flame-dried round-bottom flask containing a stirrer bar and the vessel was placed under argon. DCM (2 mL) was added to the flask, followed by aldehyde 1 in DCM (137 mg, 0.59 mmol, 1.00 eq., in 1 mL DCM) and amine 2a (200 mg, 0.59 mmol, 1.00 eq. in 1 mL DCM). The reaction was left to stir at room temperature for 24 hours before the reaction mixture was filtered through a sinter funnel and washed with anhydrous DCM. The solution was concentrated in vacuo to afford imine 3a (317 mg, 97% yield).

Reference： [1]Nguyen, Remi; Allouche, Lionel; Buhler, Eric; Giuseppone, Nicolas [Angewandte Chemie - International Edition, 2009, vol. 48, # 6, p. 1093 - 1096]
[2]Morrow, Sarah M.; Bissette, Andrew J.; Fletcher, Stephen P. [Tetrahedron, 2017, vol. 73, # 33, p. 5005 - 5010]

6
[ 4437-01-8 ]
[ 170572-38-0 ]

Reference： [1]Chemistry - An Asian Journal,2010,vol. 5,p. 1163 - 1170
[2]Tetrahedron,2017,vol. 73,p. 5005 - 5010
[3]European Journal of Organic Chemistry,2017,vol. 2017,p. 4461 - 4468

7
[ 79622-11-0 ]
[ 170572-38-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: 2,5,8,11,14,17,20-heptaoxadocosan-22-yl 4-methylbenzenesulfonate With Caswell No_. 744A In N,N-dimethyl-formamide at 110℃; for 3h; Stage #2: With triphenylphosphine In tetrahydrofuran at 20℃; for 18h; Inert atmosphere;
	Multi-step reaction with 2 steps 1.1: Caswell No_. 744A / N,N-dimethyl-formamide / 5 h / 80 °C 2.1: triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C 2.2: 20 °C
	Multi-step reaction with 2 steps 1: Caswell No_. 744A / ethanol / 78 °C 2: lithium aluminium hydride / diethyl ether; tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

Reference： [1]Matsumoto, Sayaka; Iwamoto, Hiroya; Mizutani, Tadashi [Chemistry - An Asian Journal, 2010, vol. 5, # 5, p. 1163 - 1170]
[2]Liu, Xin; Yuan, Yaping; Bo, Shaowei; Li, Yu; Yang, Zhigang; Zhou, Xin; Chen, Shizhen; Jiang, Zhong-Xing [European Journal of Organic Chemistry, 2017, vol. 2017, # 30, p. 4461 - 4468]
[3]Li, Han; Wenger, Oliver S. [Angewandte Chemie - International Edition, 2022, vol. 61, # 5][Angew. Chem., 2022, vol. 134, # 5]

8
[ 170572-38-0 ]
[ 561316-60-7 ]
[ 1417621-93-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	In ethyl acetate for 12h; Reflux;	9 EXAMPLE 9 To a suspension of 4.38 g of 2-(1-imidazolylcarbo- nylamino)-6-methyl-4[1 H]-pyrimidinone l (0.02 mol) in 200 ml ofethyl acetatewere added7.4 gof2,5,8,11,14,17,20 heptaoxadocosan-22-amine (0.02 18 mol). The reaction mixture was refluxed for 12 hours. The mixture was then allowed to return to room temperature, and was evaporated under reduced pressure. The residue was taken up in acetone (50 ml) and then filtered to remove the imidazole. The filtrate was evaporated under reduced pressure and then taken up again in 50 ml of acetone and filtered. The filtrate was evaporated under reduced pressure. 5.9 g of the expected product were thus obtained in the form of a pasty oil, in a yield of 60%. 1 H and 13C NMR spectra compliant.

Reference： [1]Current Patent Assignee: L'OREAL SA - US2014/155352, 2014, A1 Location in patent: Paragraph 0947; 0948

9
[ 170572-38-0 ]
[ 1384595-05-4 ]
tert-butyl (4-((2-((3-(2,5,8,11,14,17,20-heptaoxadocosan-22-ylcarbamoyl)-5-methoxyphenyl)amino)pyrimidin-4-yl)oxy)naphthalen-1-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.01 g	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane; ethyl acetate at 20℃;	40.i tert-Butyl (4-((2-((3-(2,5,8,11,14,17,20-heptaoxadocosan-22-ylcarbamoyl)-5-methoxyphenyl)amino)pyrimidin-4-yl)oxy)naphthalen-1-yl)carbamate A stirred mixture of 3-((4-((4-((tert-butoxycarbonyl)amino)naphthalen-1-yl)oxy)pyrimidin-2-yl)amino)-5-methoxybenzoic acid (see Example 6(i) above; 800 mg, 1.592 mmol), 2,5,8,11,14,17,20-heptaoxadocosan-22-amine (513 mg, 1.512 mmol) and triethylamine (666 μL, 4.78 mmol) in DCM (60 mL) was cooled in an ice-bath. 50 wt % T3P in EtOAc (1422 μL, 2.388 mmol) was added, the ice-bath was removed and the reaction mixture allowed to warm to rt and stirred at this temperature for overnight. The reaction mixture was partitioned between sat. aq. NaHCO3 (100 mL) and DCM (100 mL). The aqueous phase was back extracted with fresh DCM (50 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo onto silica gel. The crude product was purified by chromatography on the Companion (80 g column, 2-5% MeOH in DCM) to afford the sub-title compound (1.01 g) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ: 9.60 (s, 1H), 9.33 (s, 1H), 8.42 (d, 1H), 8.32 (t, 1H), 8.11 (d, 1H), 7.82 (d, 1H), 7.54-7.63 (m, 4H), 7.39-7.42 (m, 2H), 6.91 (s, 1H), 6.55 (d, 1H), 3.58 (s, 3H), 3.48-3.52 (m, 24H), 3.37-3.43 (m, 4H), 3.23 (s, 3H), 1.52 (s, 9H). LCMS m/z 385 (M-tBu+2H)2+ (ES+)
1.01 g	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane at 20℃;	40.i (i) tert-Butyl (4-((2-((3-(2, 5,8,11 14,1 7,20-heptaoxadocosan-22-ylcarbamoyl)-5-methoxyphenyl)am ino)pyrimidin-4-yl)oxy)naphthalen- 1 -yl)carbamate A stirred mixture of 3-((4-((4-((tert-butoxycarbonyl)amino)naphthalen- 1 -yl)oxy)pyrimidin-2- yl)amino)-5-methoxybenzoic acid (see Example 6(i) above; 800 mg, 1.592 mmol), 2,5,8,11 ,14,17,20-heptaoxadocosan-22-amine (513 mg, 1.512 mmol) and triethylamine (666 pL, 4.78 mmol) in DCM (60 mL) was cooled in an ice-bath. 50 wt% T3P in EtOAc (1422 pL,2.388 mmol) was added, the ice-bath was removed and the reaction mixture allowed to warm to rt and stirred at this temperature for overnight. The reaction mixture was partitioned between sat. aq. NaHCO3 (100 mL) and DCM (100 mL). The aqueous phase was back extracted with fresh DCM (50 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo onto silica gel. Thecrude product was purified by chromatography on the Companion (80 g column, 2-5% MeOH in DCM) to afford the sub-title compound (1.01 g) as a white solid.1H NMR (400 MHz, DMSO-d6) O: 9.60 (5, 1H), 9.33 (5, 1H), 8.42 (d, 1H), 8.32 (t, 1H), 8.11 (d, 1H), 7.82 (d, 1H), 7.54-7.63 (m, 4H), 7.39-7.42 (m, 2H), 6.91 (5, 1H), 6.55 (d, 1H), 3.58 (5, 3H), 3.48-3.52 (m, 24H), 3.37-3.43 (m, 4H), 3.23 (5, 3H), 1.52 (5, 9H).LCMS mlz 385 (M-tBu+2H)2+ (ES)

Reference： [1]Current Patent Assignee: OXULAR LTD - US2014/296208, 2014, A1 Location in patent: Paragraph 0969 - 0971
[2]Current Patent Assignee: OXULAR LTD - WO2014/162126, 2014, A1 Location in patent: Page/Page column 102; 103

10
[ 170572-38-0 ]
2,5,8,11,14,17,20-heptaoxadocosan-22-ylsulfamoyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With sulfuryl dichloride; triethylamine In dichloromethane at -78 - 20℃; for 2h;	54.1 Step 1 : Preparation of 2,5,8,1 1 , 14, 17,20-heptaoxadocosan-22-ylsulfamoyl To a solution of mPEG7-NH2 (2.5 g, 7.36 mmol) in dichloromethane (25 mL) was added triethyl amine (2.1 μ, 15.5 mmol). The mixture was cooled to -78 °C. A solution of sulfuryl chloride (1.2 mL, 14.72 mmol) in dichloromethane (12 mL) was slowly added to the above reaction mixture, making sure temperature of reaction mixture did not increase above -50 °C. After the addition, the reaction mixture was slowly warmed to ambient temperature and thereafter stirred for additional two hours. The reaction mixture was then quenched into ice-cold water and stirred for 15 minutes. The organic layer was separated, dried over anhydrous sodium sulfate, and concentrated under vacuum to give 2,5,8, 1 1 , 14,17,20-heptaoxadocosan-22-ylsulfamoyl chloride (2.5 g, 77% yield) which was used directly for the next step.

Reference： [1]Current Patent Assignee: TPG SPECIALTY LENDING, INC.; NEKTAR THERAPEUTICS - WO2014/210436, 2014, A2 Location in patent: Paragraph 00542; 00543

11
[ 170572-38-0 ]
(S)-N-(1-(3-((N-(2,5,8,11,14,17,20-heptaoxadocosan-22-yl)sulfamoyl)amino)phenyl)-2-(pyrrolidin-1-yl)ethyl)-2-(3,4-dichlorophenyl)-N-methylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sulfuryl dichloride; triethylamine / dichloromethane / 2 h / -78 - 20 °C 2: triethylamine / dichloromethane / 18 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: TPG SPECIALTY LENDING, INC.; NEKTAR THERAPEUTICS - WO2014/210436, 2014, A2

12
[ 170572-38-0 ]
[ 1122596-42-2 ]
(2S,6R,11R)-3-(cyclopropylmethyl)-8-(2,5,8,11,14,17,20-heptaoxadocosan-22-ylamino)-6,11-dimethyl-3,4,5,6-tetrahydro-2,6-methano-3-benzazocin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	In 1-methyl-pyrrolidin-2-one at 200℃; for 2h; Microwave irradiation;	3 Example 3 Preparation of (2S,6R,llR)-3-(Cyclopropylmethyl)-8-(2,5,8,l 1,14,17,20- heptaoxadocosan-22-ylamino)-6,ll-dimethyl-3,4,5,6-tetrahydro-2,6-methano-3- benzazocin-l(2H)-one (3) [00220] (2S,6R,117?)-3-(Cyclopropylmethyl)-6,l l-dimethyl-l-oxo-l,2,3,4,5,6- hexahydro-2,6-methano-3-benzazocin-8-yl trifluoromethanesulfonate (0.10 g, 0.24 mmol) (from Example 1 , step 1), 2,5,8,1 1,14,17,20-heptaoxadocosan-22-amine (0.18 g, 0.73 mmol) and l-methyl-2-pyrrolidinone (3 mL) were added to a 2-5 mL microwave vial, and then heated under microwave irradiation for 2 hours at 200 °C. The reaction mixture was cooled to room temperature, poured into 12 mL water and extracted with methyl tert-butyl ether (3 x 5 mL). The combined organic portions were washed with water (20 mL) and saturated sodium chloride (20 mL) and then dried over anhydrous sodium sulfate. The residue was purified by silica gel chromatography using methanol/dichloromethane (1 :9) as eluent to give 0.08 g (55%) of (2S, 6R,l li?)-3-(cyclopropylmethyl)-8-(2,5,8,l l,14,17,20-heptaoxadocosan- 22-ylamino)-6,1 l-dimethyl-3,4,5,6-tetrahydro-2,6-methano-3-benzazocin-l(2H)-one as a yellow oil. NMR (500 MHz, CDC13): 7.85 (m, 1 H), 6.49 (m, l H), 6.38 (m, l H), 3.73 (m, 2H), 3.72 (m, 24H), 3.71 (m, 2H), 3.54 (m, 5H), 2.97 (m, IH), 2.75 (m, 1H), 2.15 (m, 1H), 2.01 (m, 3H), 1.49 (m, 1H), 1.38 (s, 3H), 0.89 (m, 3H), 0.48 (m, 2H), 0.46 (m, 2H), 0.25 (m, I H); MS (EI) for C33H54 208: 607 (MH+).

Reference： [1]Current Patent Assignee: NEKTAR THERAPEUTICS - WO2015/79459, 2015, A1 Location in patent: Paragraph 00220

13
[ 170572-38-0 ]
[ 120362-25-6 ]
mPEGn-ribamidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
431 mg	In methanol at 45℃; for 15.5h;	1D Synthesis of mPEG-ribamidine 11 (n=7) Synthesis of mPEG-ribamidine 11 (n=7) mPEG7-NH2 (565 mg, 1.66 mmol) was added to a stirred solution of crude methyl amidate 10(346mg, 1.34 mmol))in methanol (6.0 mE) at room temperature. The resulting mixture was heated at 45° C. for 15.5 hours. The mixture was concentrated under reduced pressure. The residue was triturated with EtOAc, diluted with ethyl ether, centrifuged. The precipitate was triturated again with DCM, diluted with ethylether and centriffiged. The precipitate was collected and dried under high vacuum to afford 431 mg of product. ‘H-NMR (MeOD) for compound 11: 8.61 (s, 1 H, C5H, triazole proton), 5.71 (d, J=3.3 Hz, 1H), 4.29 (m, 1H), 4.14 (m, 1H), 3.91 (m, 1H), 3.75-3.33 (m, 35H), 3.15 (s, 3H, CH3). LC-MS: 566.3(MHj.

Reference： [1]Current Patent Assignee: NEKTAR THERAPEUTICS - US9149538, 2015, B2 Location in patent: Page/Page column 36; 38

14
[ 170572-38-0 ]
C₃₄H₆₆N₄O₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: sodium tris(acetoxy)borohydride; acetic acid 2: tetrahydrofuran / 48 h / 70 °C / Inert atmosphere 3: acetonitrile / 24 h / 20 °C / Inert atmosphere 4: triethylamine / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

Reference： [1]Sauvée, Claire; Casano, Gilles; Abel, Sébastien; Rockenbauer, Antal; Akhmetzyanov, Dimitry; Karoui, Hakim; Siri, Didier; Aussenac, Fabien; Maas, Werner; Weber, Ralph T.; Prisner, Thomas; Rosay, Mélanie; Tordo, Paul; Ouari, Olivier [Chemistry - A European Journal, 2016, vol. 22, # 16, p. 5598 - 5606]

15
[ 170572-38-0 ]
C₂₈H₅₁N₄O₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride; acetic acid 2: tetrahydrofuran / 48 h / 70 °C / Inert atmosphere

16
[ 170572-38-0 ]
C₂₉H₅₄N₄O₉⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium tris(acetoxy)borohydride; acetic acid 2: tetrahydrofuran / 48 h / 70 °C / Inert atmosphere 3: acetonitrile / 24 h / 20 °C / Inert atmosphere

17
[ 170572-38-0 ]
[ 2896-70-0 ]
C₂₄H₄₉N₂O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid

18
C₂₃H₃₅NO₉ [ No CAS ]
[ 170572-38-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine In tetrahydrofuran; water at 20℃; for 1.7h;	To a round-bottom flask containing a stirrer bar was added phthalmide G (220 mg, 0.47 mmol, 1.00 eq.). The substrate was dissolved in THF (6.5 mL) and aqueous hydrazine was added (1.17 mL 40-50% b/w N2H4 in H2O, ~ 40.0 eq.). The reaction was stirred at room temperature for 1.7 hours before the solvent was removed in vacuo. H2O was added (15 mL) before extraction with CHCl3 (3 * 15 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to afford, without further purification, amine 2a (128 mg, 80% yield).

Reference： [1]Morrow, Sarah M.; Bissette, Andrew J.; Fletcher, Stephen P. [Tetrahedron, 2017, vol. 73, # 33, p. 5005 - 5010]

19
[ 170572-38-0 ]
C₁₅H₃₁⁽²⁾H₂NO₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: magnesium sulfate / dichloromethane / 24 h / 20 °C / Inert atmosphere; Schlenk technique 2: water-d2 / 15 h

Reference： [1]Morrow, Sarah M.; Bissette, Andrew J.; Fletcher, Stephen P. [Tetrahedron, 2017, vol. 73, # 33, p. 5005 - 5010]

20
[ 208987-04-6 ]
[ 170572-38-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: azidoheptaethylene glycol methyl ether With triphenylphosphine In tetrahydrofuran at 20℃; for 0.5h; Stage #2: With water monomer In tetrahydrofuran at 20℃;
90%	With lithium aluminium hydride In tetrahydrofuran; diethyl ether at 20℃; for 2h; Inert atmosphere;

Reference： [1]Liu, Xin; Yuan, Yaping; Bo, Shaowei; Li, Yu; Yang, Zhigang; Zhou, Xin; Chen, Shizhen; Jiang, Zhong-Xing [European Journal of Organic Chemistry, 2017, vol. 2017, # 30, p. 4461 - 4468]
[2]Li, Han; Wenger, Oliver S. [Angewandte Chemie - International Edition, 2022, vol. 61, # 5][Angew. Chem., 2022, vol. 134, # 5]

21
[ 170572-38-0 ]
C₄₁H₇₅N₃O₁₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: triethylamine; dmap / dichloromethane / 0.17 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: potassium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 45 °C / Inert atmosphere

22
[ 170572-38-0 ]
C₃₄H₆₉N₃O₁₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triethylamine; dmap / dichloromethane / 0.17 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: potassium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 45 °C / Inert atmosphere 3.1: palladium on activated charcoal; hydrogen / methanol / 20 °C

23
[ 170572-38-0 ]
C₃₆H₇₀BrN₃O₁₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triethylamine; dmap / dichloromethane / 0.17 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: potassium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 45 °C / Inert atmosphere 3.1: palladium on activated charcoal; hydrogen / methanol / 20 °C 4.1: triethylamine; dmap / dichloromethane / 0.17 h / 0 °C / Inert atmosphere 4.2: 0 - 20 °C / Inert atmosphere

24
[ 170572-38-0 ]
[ 598-21-0 ]
C₁₇H₃₄BrNO₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: 2,5,8,11,14,17,20-heptaoxadocosan-22-amine With dmap; triethylamine In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 2-Bromoacetyl bromide In dichloromethane at 0 - 20℃; Inert atmosphere;

25
[ 112-35-6 ]
[ 170572-38-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / Inert atmosphere 1.2: 20 °C / pH 3 / Inert atmosphere 2.1: sodium hydroxide / tetrahydrofuran; water / 0.17 h 2.2: 0 - 20 °C 3.1: sodium azide / N,N-dimethyl-formamide / 5 h / 80 °C 4.1: triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C 4.2: 20 °C

26
1,3,6,9,12-pentaoxa-2-thiacyclotetradecane 2,2-dioxide [ No CAS ]
[ 170572-38-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / Inert atmosphere 1.2: 20 °C / pH 3 / Inert atmosphere 2.1: sodium hydroxide / tetrahydrofuran; water / 0.17 h 2.2: 0 - 20 °C 3.1: sodium azide / N,N-dimethyl-formamide / 5 h / 80 °C 4.1: triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C 4.2: 20 °C

27
[ 170572-38-0 ]
[ 1663-39-4 ]
C₂₂H₄₅NO₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
324 mg	In ethanol at 20℃; for 72h;	11.1 Synthesis of compound 28. To a solution of H2-PEG(7u)-OMe (300 mg) in ethanol (2.5 mL) was added tert-butyl acrylate (194 μ.) and the reaction mixture was stirred at room temperature for 72 h. The solution was concentrated in vacuo and purified by normal phase chromatography eluting with dichloromethane: methanol (100:0 v/v to 70:30 v/v). The solvent was removed in vacuo to give compound 28 as a pale yellow oil (324 mg). m/z [M+H]+ (468, 100%).

Reference： [1]Current Patent Assignee: WELSH, CARSON, ANDERSON & STOWE - WO2017/178828, 2017, A1 Location in patent: Page/Page column 66

28
[ 170572-38-0 ]
C₄₇H₆₇NO₁₅S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: ethanol / 72 h / 20 °C 2.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-methyl-morpholine / N,N-dimethyl-formamide / 1 h / 0 - 20 °C 2.2: 5 h

Reference： [1]Current Patent Assignee: WELSH, CARSON, ANDERSON & STOWE - WO2017/178828, 2017, A1

29
[ 170572-38-0 ]
C₄₃H₅₉NO₁₅S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: ethanol / 72 h / 20 °C 2.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-methyl-morpholine / N,N-dimethyl-formamide / 1 h / 0 - 20 °C 2.2: 5 h 3.1: trifluoroacetic acid / dichloromethane / 17 h / 0 - 4 °C

Reference： [1]Current Patent Assignee: WELSH, CARSON, ANDERSON & STOWE - WO2017/178828, 2017, A1

30
[ 170572-38-0 ]
[ 128-69-8 ]
C₅₄H₇₀N₂O₁₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With 1H-imidazole; Zinc acetate at 160℃; for 18h; Inert atmosphere;
68%	With pyridine; Zinc acetate for 20h; Reflux;	2.2.2. Synthesis of N′,N′-Di-[10-(3,6,9,12,15,18,21-tetraoxa-docosyl)]-perylene-3,4,9,10-bis(dicarboximide) (PEG7)2PDI (2) The compound was prepared following the literature [29]. PTCDA(238 mg, 0.61 mmol), zinc acetate (145 mg, 0.80 mmol) and MeOPEG(7)-amine (450 mg, 1.33 mmol) were dissolved in pyridine (5mL) and the mixture was heated to reflux for 20 h. Then, pyridine wasremoved by rotary evaporation and the resulting solid was dissolvedin CH2Cl2 (3 mL) and precipitated using hexane. The collected purpleprecipitate was re-dissolved in CH2Cl2 (3 mL) and added dropwise toexcess of diethyl ether. After 12 h in the fridge the precipitate was collectedby filtration, washed with diethyl ether and dried under vacuumto give 2 (435mg, 68%) as dark red solid. 1H NMR (400MHz, CDCl3) δ=8.68 (d, J = 8.0 Hz, 4H, ArH), 8.62 (d, J = 8.0 Hz, 4H, ArH), 4.46(t, J=6.0 Hz, 4H, NCH2), 3.86 (t, J=6.0 Hz, 4H, NCH2CH2), 3.63 (m, 24H,OCH2CH2O),3.37(s,6H,OMe).FTIR(cm-1):2867s,1690s,1656s,1592s,1578m,1508w,1437w,1404w,1336m,1301w,1244m,1179w,1098s,1063m, 1022 m, 946w, 856w, 810m, 791w, 746w.

Reference： [1]Li, Han; Wenger, Oliver S. [Angewandte Chemie - International Edition, 2022, vol. 61, # 5][Angew. Chem., 2022, vol. 134, # 5]
[2]Pérez-Calm; Esquena; Salonen; Rodríguez-Abreu [Journal of Molecular Liquids, 2021, vol. 325]

31
[ 170572-38-0 ]
[ 3338-32-7 ]
tert-butyl (25S)-25-[(benzyloxy)carbonyl]amino}-24-oxo-2,5,8,11,14,17,20-heptaoxa-23-azaheptacosan-27-oate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine In dichloromethane at 20℃; for 1h;	34.1; 38B.1 Step 1: tert-Butyl {2-[(2R)-2-({9-[(2R,5R,7R,8R,10R,12aR,14R,15aS,16R)-16-hydroxy-2,10- dioxido-14-(pyrimidin-4-yloxy)-2,10-disulfanyldecahydro-5,8- methanocyclopenta[l][1,3,6,9,11,2,10]pentaoxadiphosphacyclotetradecin-7-yl]-6-oxo-6,9- dihydro-1H-purin-2-yl}carbamoyl)pyrrolidin-1-yl]-2-oxoethyl}carbamate General procedure: To a mixture of Intermediate 15 (60 mg, 0.05 mmol) and 2,5-dioxopyrrolidin-1-yl (tert-butoxycarbonyl)glycinate (19 mg, 0.07 mmol) in DMF (1.6 mL) was added triethylamine (50 uL, 0.355 mmol), and the reaction mixture was stirred at rt for 1 h. The reaction mixture was quenched with water, Celite was added and the reaction mixture was concentrated to dryness. The crude residue absorbed onto Celite was purified by reverse phase column chromatography (0-100% ACN/aqueous ammonium bicarbonate (5 mM)). Triethylamine (14 uL, 0.1 mmol) was added to an aqueous solution of the product. Lyophilization overnight provided tert-butyl {2- [(2R)-2-({9-[(2R,5R,7R,8R,10R,12aR,14R,15aS,16R)-16-hydroxy-2,10-dioxido-14-(pyrimidin-4- yloxy)-2,10-disulfanyldecahydro-5,8- methanocyclopenta[l][1,3,6,9,11,2,10]pentaoxadiphosphacyclotetradecin-7-yl]-6-oxo-6,9- dihydro-1H-purin-2-yl}carbamoyl)pyrrolidin-1-yl]-2-oxoethyl}carbamate as the N,N- diethylethanamine salt (49 mg, 87%). LCMS (AA): m/z = 904.4 (M+H).

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2020/229982, 2020, A1 Location in patent: Paragraph 0670; 0685; 0702

32
[ 170572-38-0 ]
tert-butyl (25S)-25-[4-(11,12-didehydrodibenzo[b,f]azocin-5(6H)-yl)-4-oxobutanoyl]amino}-24-oxo-2,5,8,11,14,17,20-heptaoxa-23-azaheptacosan-27-oate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 1 h / 20 °C 2: hydrogen; palladium 10% on activated carbon / ethanol / 3 h / 775.74 Torr 3: triethylamine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2020/229982, 2020, A1

33
[ 170572-38-0 ]
(25S)-25-[4-(11,12-didehydrodibenzo[b,f]azocin-5(6H)-yl)-4-oxobutanoyl]amino}-24-oxo-2,5,8,11,14,17,20-heptaoxa-23-azaheptacosan-27-oic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 1 h / 20 °C 2: hydrogen; palladium 10% on activated carbon / ethanol / 3 h / 775.74 Torr 3: triethylamine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 0 - 20 °C 4: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2020/229982, 2020, A1

34
[ 170572-38-0 ]
(25S)-25-([(1R,8S,9s)-bicyclo[6.1.0]non-4-yn-9-ylmethoxy]carbonyl}amino)-24-oxo- 2,5,8,11,14,17,20-heptaoxa-23-azaheptacosan-27-oic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 1 h / 20 °C 2.1: hydrogen; palladium 10% on activated carbon / ethanol / 3 h / 775.74 Torr 3.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3.2: 2 h / 20 °C

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2020/229982, 2020, A1

35
[ 170572-38-0 ]
tert-butyl (25S)-25-amino-24-oxo-2,5,8,11,14,17,20-heptaoxa-23-azaheptacosan-27-oate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 1 h / 20 °C 2: hydrogen; palladium 10% on activated carbon / ethanol / 3 h / 775.74 Torr

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2020/229982, 2020, A1

36
[ 170572-38-0 ]
4-[4-[[5-(3,4-dimethoxy-N-methylanilino)-1-(4-fluoro-3-methoxyphenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]benzoic acid [ No CAS ]
4-[4-[[5-(3,4-dimethoxy-N-methylanilino)-1-(4-fluoro-3-methoxyphenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]-N-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With benzotriazol-1-ol; triethylamine; diisopropyl-carbodiimide In dichloromethane at 20℃;

Reference： [1]Hoguet, Vanessa; Lasalle, Manuel; Maingot, Mathieu; Dequirez, Geoffroy; Boulahjar, Rajaa; Leroux, Florence; Piveteau, Catherine; Herledan, Adrien; Biela, Alexandre; Dumont, Julie; Chávez-Talavera, Oscar; Belloy, Loïc; Duplan, Isabelle; Hennuyer, Nathalie; Butruille, Laura; Lestavel, Sophie; Sevin, Emmanuel; Culot, Maxime; Gosselet, Fabien; Staels, Bart; Deprez, Benoit; Tailleux, Anne; Charton, Julie [Journal of Medicinal Chemistry, 2021, vol. 64, # 3, p. 1593 - 1610]

37
[ 170572-38-0 ]
[ 1244-58-2 ]
C₃₇H₆₁NO₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With toluene-4-sulfonic acid; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;	To a stirred solution of cannabidiolic acid (CBDA, 31.9 mg, 0.089 mmols) dissolved in 3.1 mL of anhydrous dichloromethane (DCM) in flame-dried glass vial equipped with a magnetic stir bar, m-PEG7-amine (60.4 mg, 0.178 mmols, 2 molar equivalents over CBDA), N,N′-dicyclohexylcarbodiimide, (DCC, 22 mg, 0.106 mmols) was added, then p-toluene sulfonic acid (pTSA, 3.2 mg, 0.016 mmols) was added in a sequential fashion. The reaction was stirred overnight at room temperature under an atmosphere of nitrogen to keep the reaction dry. The solvent was evaporated to dryness on a roto-evaporator. The residue was resuspended in toluene, and the solution was cooled at -20° C. overnight. The precipitated side-product N,N-dicyclohexylurea was filtered through a short pad of Celite filtering material. The filtrate was evaporated to dryness and purified by column chromatography on silica gel eluting with a gradient of 7:3 to 1:1 hexanes/acetone to give desired product in 72% yield. The mass spec and NMR data showed the correct product with a mass of 679 Da.

Reference： [1]Current Patent Assignee: AXIM BIOTECHNOLOGIES INC - US2021/332004, 2021, A1 Location in patent: Paragraph 0122-0125

38
[ 170572-38-0 ]
C₅₄H₇₀N₂O₁₈^(2-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1H-imidazole; Zinc acetate / 18 h / 160 °C / Inert atmosphere 2: sodium dihydrosulfite / water monomer / 20 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: 1H-imidazole; Zinc acetate / 18 h / 160 °C / Inert atmosphere 2: sodium dihydrosulfite / water monomer / 20 °C

Reference： [1]Li, Han; Wenger, Oliver S. [Angewandte Chemie - International Edition, 2022, vol. 61, # 5][Angew. Chem., 2022, vol. 134, # 5]
[2]Li, Han; Wenger, Oliver S. [Angewandte Chemie - International Edition, 2022, vol. 61, # 5][Angew. Chem., 2022, vol. 134, # 5]

39
[ 170572-38-0 ]
[ 118129-60-5 ]
C₅₄H₆₈Br₂N₂O₁₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%	With propionic acid at 120℃; Inert atmosphere;

Reference： [1]Li, Han; Wenger, Oliver S. [Angewandte Chemie - International Edition, 2022, vol. 61, # 5][Angew. Chem., 2022, vol. 134, # 5]

40
[ 170572-38-0 ]
[ 118129-60-5 ]
C₅₄H₆₈Br₂N₂O₁₈^(2-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: propionic acid / 120 °C / Inert atmosphere 2: sodium dihydrosulfite / water monomer / 20 °C / Inert atmosphere

Reference： [1]Li, Han; Wenger, Oliver S. [Angewandte Chemie - International Edition, 2022, vol. 61, # 5][Angew. Chem., 2022, vol. 134, # 5]

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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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Health hazards
Code	Phrase
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H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
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H319	Causes serious eye irritation
H320	Causes eye irritation
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ 170572-38-0 ] Synthesis Path-Downstream 1~40

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