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10-(Benzyloxy)-10-oxodecanoic acid
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[ CAS No. 67852-88-4 ] {[proInfo.proName]}

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Chemical Structure| 67852-88-4
Chemical Structure| 67852-88-4
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Quality Control of [ 67852-88-4 ]

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SDS Specification
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Product Details of [ 67852-88-4 ]

CAS No. :67852-88-4 MDL No. :MFCD30589211
Formula : C17H24O4 Boiling Point : -
Linear Structure Formula :- InChI Key :RARFDGQRJGLQCZ-UHFFFAOYSA-N
M.W : 292.37 Pubchem ID :14250265
Synonyms :

Safety of [ 67852-88-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 67852-88-4 ]

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

  • Downstream synthetic route of [ 67852-88-4 ]

[ 67852-88-4 ] Synthesis Path-Downstream   1~52

  • 1
  • [ 111-20-6 ]
  • [ 100-44-7 ]
  • [ 140-24-9 ]
  • [ 67852-88-4 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In toluene for 4.5h; Heating; Yield given;
Reference： [1]Zerda, Jaime de la; Barak, Gabriela; Sasson, Yoel [Tetrahedron, 1989, vol. 45, # 5, p. 1533 - 1536]
  • 2
  • [ 251922-72-2 ]
  • [ 67852-88-4 ]
YieldReaction ConditionsOperation in experiment
With ammonium formate; 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) In dimethyl sulfoxide at 50℃; for 12h;
Reference： [1]Boutros, Andre; Legros, Jean-Yves; Fiaud, Jean-Claude [Tetrahedron Letters, 1999, vol. 40, # 41, p. 7329 - 7332]
  • 3
  • [ 67852-88-4 ]
  • [ 74-88-4 ]
  • methyl phenylmethyldecanedioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In dimethyl sulfoxide at 20℃; for 12h;
Reference： [1]Boutros, Andre; Legros, Jean-Yves; Fiaud, Jean-Claude [Tetrahedron Letters, 1999, vol. 40, # 41, p. 7329 - 7332]
  • 4
  • [ 123-99-9 ]
  • [ 100-51-6 ]
  • [ 18107-18-1 ]
  • [ 67852-88-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: azelaic acid; benzyl alcohol; diazomethyl-trimethyl-silane Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 0.5h;
Reference： [1]Iso, Yasuyoshi; Shindo, Hirohisa; Hamana, Hiroshi [Tetrahedron, 2000, vol. 56, # 30, p. 5353 - 5361]
  • 5
  • [ 67852-88-4 ]
  • [ 67852-87-3 ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 2h;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0℃;
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide 5.2.5. Benzyl (-)-14-methoxy-butorphanol-3-yl decanedioate (13b) Method A: To the solution of sebacic acid monobenzyl ester (1.08 g, 3.53 mmol) in anhydrous CH2Cl2 (15 mL) was added oxalyl chloride (0.62 mL, 7.04 mmol) and two drops of DMF. Gas evolution could be observed and the solution was stirred overnight. Next, CH2Cl2 and excess oxalyl chloride was removed under reduced pressure. The yellow oil was redissolved in anhydrous CH2Cl2. 14-Methoxy-butorphanol (8) (1.00 g, 2.93 mmol) and Et3N (2.0 mL, 14.1 mmol) was added to the solution and the mixture was stirred overnight. The organic layer was washed with NaHCO3 solution and dried over Na2SO4. After solvent was removed under reduced pressure, the crude product was purified on silica gel (EtOAc/hexanes 1:4 and EtOAc/hexanes 1:1) to give a yellow oil (460 mg, 25%).
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; Synthesis of monobenzyl sebacoyl chloride (Supplementary material, Scheme S1) The procedure was adapted from Abell, Morris, and Litten (1990), as follows. Monobenzyl sebacate (0.051mol, 15.00g) was dissolved in dichloromethane (300mL), then DMF (5 drops) was added. The solution was cooled in an ice bath to 0°C. Oxalyl chloride (24.42mL, 5.6equiv.) was added slowly. The ice bath was removed and the reaction proceeded at room temperature. A halt in gas evolution indicated completion, then solvent was removed under reduced pressure. Toluene (50mL) was added and the product concentrated azeotropically under reduced pressure. The product was stored and used in this crude form without further purification.
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; Synthesis of monobenzyl sebacoyl chloride (Supplementarymaterial, Scheme S1 ). General procedure: The procedure was adapted from Abell,Morris, and Litten (1990), as follows. Monobenzyl sebacate(0.051 mol, 15.00 g) was dissolved in dichloromethane (300 mL),then DMF (5 drops) was added. The solution was cooled in anice bath to 0 C. Oxalyl chloride (24.42 mL, 5.6 equiv.) was addedslowly. The ice bath was removed and the reaction proceededat room temperature. A halt in gas evolution indicated completion, then solvent was removed under reduced pressure. Toluene(50 mL) was added and the product concentrated azeotropically under reduced pressure. The product was stored and used in thiscrude form without further purification. Yield: 90.1% (0.046 mol,14.35 g). 1 H NMR (CDCl3): 1.30 (m, 8H), 1.67 (m, 4H), 2.35 (t, 2H),2.86 (t, 2H), 5.11 (s, 2H), 7.35 (m, 5H).

Reference： [1]Peng, Xuemei; Knapp, Brian I.; Bidlack, Jean M.; Neumeyer, John L. [Journal of Medicinal Chemistry, 2006, vol. 49, # 1, p. 256 - 262]
[2]Location in patent: experimental part Qian, Shan; Li, Haijiao; Chen, Yin; Zhang, Weiyu; Yang, Shengyong; Wu, Yong [Journal of Natural Products, 2010, vol. 73, # 11, p. 1743 - 1750]
[3]Location in patent: experimental part Zhang, Bin; Zhang, Tangzhi; Sromek, Anna W.; Scrimale, Thomas; Bidlack, Jean M.; Neumeyer, John L. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 9, p. 2808 - 2816]
[4]Liu, Haoyu; Ilevbare, Grace A.; Cherniawski, Benjamin P.; Ritchie, Earl T.; Taylor, Lynne S.; Edgar, Kevin J. [Carbohydrate Polymers, 2014, vol. 100, p. 116 - 125]
[5]Liu, Haoyu; Ilevbare, Grace A.; Cherniawski, Benjamin P.; Ritchie, Earl T.; Taylor, Lynne S.; Edgar, Kevin J. [Carbohydrate Polymers, 2014, vol. 100, p. 116 - 125]
  • 6
  • [ 67852-88-4 ]
  • [ 874213-31-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: oxalyl chloride; DMF / CH2Cl2 / 2 h / 0 - 20 °C 2: 90.7 percent / Et3N / 0 - 20 °C 3: 85.6 percent / H2 / Pd/C / ethyl acetate / 20 °C 4: oxalyl chloride; DMF / CH2Cl2 / 2 h / 0 - 20 °C
Reference： [1]Peng, Xuemei; Knapp, Brian I.; Bidlack, Jean M.; Neumeyer, John L. [Journal of Medicinal Chemistry, 2006, vol. 49, # 1, p. 256 - 262]
  • 7
  • [ 67852-88-4 ]
  • [ 874213-30-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: oxalyl chloride; DMF / CH2Cl2 / 2 h / 0 - 20 °C 2: 90.7 percent / Et3N / 0 - 20 °C 3: 85.6 percent / H2 / Pd/C / ethyl acetate / 20 °C
Reference： [1]Peng, Xuemei; Knapp, Brian I.; Bidlack, Jean M.; Neumeyer, John L. [Journal of Medicinal Chemistry, 2006, vol. 49, # 1, p. 256 - 262]
  • 8
  • [ 67852-88-4 ]
  • 1-phenyl 10-((-)-N-cyclobutylmethylmorphinan-3-yl)sebacoylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: oxalyl chloride; DMF / CH2Cl2 / 2 h / 0 - 20 °C 2: 90.7 percent / Et3N / 0 - 20 °C 3: 85.6 percent / H2 / Pd/C / ethyl acetate / 20 °C 4: oxalyl chloride; DMF / CH2Cl2 / 2 h / 0 - 20 °C 5: Et3N / 0 - 25 °C
Multi-step reaction with 4 steps 1: oxalyl chloride; DMF / CH2Cl2 / 2 h / 0 - 20 °C 2: 90.7 percent / Et3N / 0 - 20 °C 3: 85.6 percent / H2 / Pd/C / ethyl acetate / 20 °C 4: 72.2 percent / 4-(dimethylamino)pyridine; N,N'-dicyclohexylcarbodiimide / CH2Cl2 / 20 °C
Reference： [1]Peng, Xuemei; Knapp, Brian I.; Bidlack, Jean M.; Neumeyer, John L. [Journal of Medicinal Chemistry, 2006, vol. 49, # 1, p. 256 - 262]
[2]Peng, Xuemei; Knapp, Brian I.; Bidlack, Jean M.; Neumeyer, John L. [Journal of Medicinal Chemistry, 2006, vol. 49, # 1, p. 256 - 262]
  • 9
  • [ 67852-88-4 ]
  • [ 874213-29-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: oxalyl chloride; DMF / CH2Cl2 / 2 h / 0 - 20 °C 2: 90.7 percent / Et3N / 0 - 20 °C
Reference： [1]Peng, Xuemei; Knapp, Brian I.; Bidlack, Jean M.; Neumeyer, John L. [Journal of Medicinal Chemistry, 2006, vol. 49, # 1, p. 256 - 262]
  • 10
  • [ 67852-88-4 ]
  • 1-((-)-N-cyclobutylmethylmorphinan-3-yl) 10-(3,6-diol-7,8-didehydro-4,5-epoxy-17-methyl-(5α,6α)morphinan-3-yl)sebacoylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: oxalyl chloride; DMF / CH2Cl2 / 2 h / 0 - 20 °C 2: 90.7 percent / Et3N / 0 - 20 °C 3: 85.6 percent / H2 / Pd/C / ethyl acetate / 20 °C 4: oxalyl chloride; DMF / CH2Cl2 / 2 h / 0 - 20 °C 5: Et3N / 0 - 25 °C
Multi-step reaction with 4 steps 1: oxalyl chloride; DMF / CH2Cl2 / 2 h / 0 - 20 °C 2: 90.7 percent / Et3N / 0 - 20 °C 3: 85.6 percent / H2 / Pd/C / ethyl acetate / 20 °C 4: 62.2 percent / 4-(dimethylamino)pyridine; N,N'-dicyclohexylcarbodiimide / CH2Cl2 / 20 °C
Reference： [1]Peng, Xuemei; Knapp, Brian I.; Bidlack, Jean M.; Neumeyer, John L. [Journal of Medicinal Chemistry, 2006, vol. 49, # 1, p. 256 - 262]
[2]Peng, Xuemei; Knapp, Brian I.; Bidlack, Jean M.; Neumeyer, John L. [Journal of Medicinal Chemistry, 2006, vol. 49, # 1, p. 256 - 262]
  • 11
  • [ 67852-88-4 ]
  • 1-((-)-N-cyclopropylmethylmorphinan-3-yl) 10-((+)-N-cyclobutylmethylmorphinan-3-yl)sebacoylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: oxalyl chloride; DMF / CH2Cl2 / 2 h / 0 - 20 °C 2: 90.7 percent / Et3N / 0 - 20 °C 3: 85.6 percent / H2 / Pd/C / ethyl acetate / 20 °C 4: oxalyl chloride; DMF / CH2Cl2 / 2 h / 0 - 20 °C 5: Et3N / 0 - 25 °C
Multi-step reaction with 4 steps 1: oxalyl chloride; DMF / CH2Cl2 / 2 h / 0 - 20 °C 2: 90.7 percent / Et3N / 0 - 20 °C 3: 85.6 percent / H2 / Pd/C / ethyl acetate / 20 °C 4: 80.9 percent / 4-(dimethylamino)pyridine; N,N'-dicyclohexylcarbodiimide / CH2Cl2 / 20 °C
Reference： [1]Peng, Xuemei; Knapp, Brian I.; Bidlack, Jean M.; Neumeyer, John L. [Journal of Medicinal Chemistry, 2006, vol. 49, # 1, p. 256 - 262]
[2]Peng, Xuemei; Knapp, Brian I.; Bidlack, Jean M.; Neumeyer, John L. [Journal of Medicinal Chemistry, 2006, vol. 49, # 1, p. 256 - 262]
  • 12
  • [ 67852-88-4 ]
  • 1-((-)-N-cyclobutylmethylmorphinan-3-yl) 10-((+)-N-cyclobutylmethylmorphinan-3-yl)sebacoylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: oxalyl chloride; DMF / CH2Cl2 / 2 h / 0 - 20 °C 2: 90.7 percent / Et3N / 0 - 20 °C 3: 85.6 percent / H2 / Pd/C / ethyl acetate / 20 °C 4: 73.1 percent / 4-(dimethylamino)pyridine; N,N'-dicyclohexylcarbodiimide / CH2Cl2 / 20 °C
Multi-step reaction with 5 steps 1: oxalyl chloride; DMF / CH2Cl2 / 2 h / 0 - 20 °C 2: 90.7 percent / Et3N / 0 - 20 °C 3: 85.6 percent / H2 / Pd/C / ethyl acetate / 20 °C 4: oxalyl chloride; DMF / CH2Cl2 / 2 h / 0 - 20 °C 5: Et3N / 0 - 25 °C
Reference： [1]Peng, Xuemei; Knapp, Brian I.; Bidlack, Jean M.; Neumeyer, John L. [Journal of Medicinal Chemistry, 2006, vol. 49, # 1, p. 256 - 262]
[2]Peng, Xuemei; Knapp, Brian I.; Bidlack, Jean M.; Neumeyer, John L. [Journal of Medicinal Chemistry, 2006, vol. 49, # 1, p. 256 - 262]
  • 13
  • [ 67852-88-4 ]
  • MCL-414 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: oxalyl chloride; DMF / CH2Cl2 / 2 h / 0 - 20 °C 2: 90.7 percent / Et3N / 0 - 20 °C 3: 85.6 percent / H2 / Pd/C / ethyl acetate / 20 °C 4: oxalyl chloride; DMF / CH2Cl2 / 2 h / 0 - 20 °C 5: Et3N / 0 - 25 °C
Multi-step reaction with 4 steps 1: oxalyl chloride; DMF / CH2Cl2 / 2 h / 0 - 20 °C 2: 90.7 percent / Et3N / 0 - 20 °C 3: 85.6 percent / H2 / Pd/C / ethyl acetate / 20 °C 4: 42.7 percent / 4-(dimethylamino)pyridine; N,N'-dicyclohexylcarbodiimide / CH2Cl2 / 20 °C
Reference： [1]Peng, Xuemei; Knapp, Brian I.; Bidlack, Jean M.; Neumeyer, John L. [Journal of Medicinal Chemistry, 2006, vol. 49, # 1, p. 256 - 262]
[2]Peng, Xuemei; Knapp, Brian I.; Bidlack, Jean M.; Neumeyer, John L. [Journal of Medicinal Chemistry, 2006, vol. 49, # 1, p. 256 - 262]
  • 14
  • [ 67852-88-4 ]
  • benzyl Chloromethyl Sebacate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; tetra(n-butyl)ammonium hydrogen sulfate In chlorobromomethane; chloroform; water; ethyl acetate 22 Benzyl Chloromethyl Sebacate EXAMPLE 22 Benzyl Chloromethyl Sebacate To a mixture of 48.67 g (0.155 mole) monobenzyl sebacate, 26.04 g (0.310 mole) sodium bicarbonate, 200 ml water and 52.55 g (0.155 mole) tetrabutylammonium hydrogen sulfate is added 100 ml chloroform. After shaking, the organic layer is separated, the aqueous phase extracted again with chloroform and the combined chloroform layers dried (Na2 SO4). Evaporation of solvent affords a residue which is taken up in 50 ml bromochloromethane and stirred overnight at room temperature. The mixture is evaporated in vacuo, the residue mixed with ethyl acetate, filtered and the filtrate concentrated in vacuo. The residual crude product is purified by column chromatography on silica gel to afford 2 g of purified monoester as an oil. 1 H-NMR (CDCl3) ppm (delta): 1.1-1.9 (m, 12H), 2.2-2.5 (m, 4H), 5.0 (s, 2H), 5.6 (s, 2H), 7.3 (s, 5H).
Reference： [1]Current Patent Assignee: PFIZER INC - US4457924, 1984, A
  • 15
  • [ 67852-88-4 ]
  • 5-fluoro-1-(hydroxymethyl) pyrimidine-2,4-(1H,3H)-dione [ No CAS ]
  • [ 1190935-67-1 ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In acetonitrile at 20℃; for 24h;
Reference： [1]Location in patent: experimental part Qian, Shan; Wu, Jian-Bo; Wu, Xiao-Chun; Li, Jie; Wu, Yong [Archiv der Pharmazie, 2009, vol. 342, # 9, p. 513 - 520]
  • 16
  • [ 1310086-72-6 ]
  • [ 67852-88-4 ]
  • [ 1310086-87-3 ]
YieldReaction ConditionsOperation in experiment
31% With dmap; dicyclohexyl-carbodiimide In dichloromethane 5.2.5. Benzyl (-)-14-methoxy-butorphanol-3-yl decanedioate (13b) Method A: To the solution of sebacic acid monobenzyl ester (1.08 g, 3.53 mmol) in anhydrous CH2Cl2 (15 mL) was added oxalyl chloride (0.62 mL, 7.04 mmol) and two drops of DMF. Gas evolution could be observed and the solution was stirred overnight. Next, CH2Cl2 and excess oxalyl chloride was removed under reduced pressure. The yellow oil was redissolved in anhydrous CH2Cl2. 14-Methoxy-butorphanol (8) (1.00 g, 2.93 mmol) and Et3N (2.0 mL, 14.1 mmol) was added to the solution and the mixture was stirred overnight. The organic layer was washed with NaHCO3 solution and dried over Na2SO4. After solvent was removed under reduced pressure, the crude product was purified on silica gel (EtOAc/hexanes 1:4 and EtOAc/hexanes 1:1) to give a yellow oil (460 mg, 25%).Method B: To the solution of sebacic acid monobenzyl ester (206 mg, 0.676 mmol) and 14-methoxy-butorphanol (192 mg, 0.563 mmol) in anhydrous CH2Cl2 (6 mL) was added DCC (139 mg, 0.676 mmol), and DMAP (7 mg, 0.0563 mmol), and the reaction mixture was stirred overnight. The next day, after solvent was removed under reduced pressure, the residue was redissolved in an equal volume of ethyl acetate and the white solid was filtered off. The organic layer was washed with saturated NaHCO3 solution and brine, and dried over Na2SO4. The crude product was purified on silica gel (EtOAc/hexanes 1:1) to a give yellow oil (110 mg, 31%).1H NMR (300 MHz, CDCl3) δ 7.35 (m, 5H), 7.09 (d, J = 8.3, 1H), 6.92 (s, 1H), 6.85 (dd, J = 2.3, 8.2, 1H), 5.12 (s, 2H), 3.22 (s, 3H), 3.16 (d, J = 18.5, 1H), 3.02 (d, J = 5.4, 1H), 2.60-1.20 (m, 37H), 0.89 (d, J = 11.1, 1H); 13C NMR (75 MHz, CDCl3) δ 173.5, 172.3, 149.3, 143.3, 136.0, 134.2, 128.4, 128.1, 118.5, 118.1, 74.0, 66.0, 61.2, 52.8, 46.9, 45.6, 42.0, 35.6, 34.3, 34.24, 34.19, 29.1, 29.0, 28.9, 28.0, 27.1, 25.4, 25.0, 24.81, 24.78, 21.4, 20.8, 18.7. Mp (HCl salt): 165-168 °C. Anal. Calcd for C39H53NO5·HCl 2.5H2O: C, 67.17; H, 8.53; N, 2.01. Found: C, 67.21; H, 8.35; N, 2.22.
Reference： [1]Location in patent: experimental part Zhang, Bin; Zhang, Tangzhi; Sromek, Anna W.; Scrimale, Thomas; Bidlack, Jean M.; Neumeyer, John L. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 9, p. 2808 - 2816]
  • 17
  • [ 67852-88-4 ]
  • C39H53NO5*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide 2: triethylamine / dichloromethane 3: hydrogenchloride / diethyl ether; ethyl acetate
Multi-step reaction with 2 steps 1: dmap; dicyclohexyl-carbodiimide / dichloromethane 2: hydrogenchloride / diethyl ether; ethyl acetate
Reference： [1]Zhang, Bin; Zhang, Tangzhi; Sromek, Anna W.; Scrimale, Thomas; Bidlack, Jean M.; Neumeyer, John L. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 9, p. 2808 - 2816]
[2]Zhang, Bin; Zhang, Tangzhi; Sromek, Anna W.; Scrimale, Thomas; Bidlack, Jean M.; Neumeyer, John L. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 9, p. 2808 - 2816]
  • 18
  • [ 67852-88-4 ]
  • [ 1310086-91-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide 2: triethylamine / dichloromethane 3: palladium on carbon; hydrogen / methanol / 20 °C
Multi-step reaction with 2 steps 1: dmap; dicyclohexyl-carbodiimide / dichloromethane 2: palladium on carbon; hydrogen / methanol / 20 °C
Reference： [1]Zhang, Bin; Zhang, Tangzhi; Sromek, Anna W.; Scrimale, Thomas; Bidlack, Jean M.; Neumeyer, John L. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 9, p. 2808 - 2816]
[2]Zhang, Bin; Zhang, Tangzhi; Sromek, Anna W.; Scrimale, Thomas; Bidlack, Jean M.; Neumeyer, John L. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 9, p. 2808 - 2816]
  • 19
  • [ 67852-88-4 ]
  • [ 1310087-01-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide 2: triethylamine / dichloromethane 3: palladium on carbon; hydrogen / methanol / 20 °C 4: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 °C
Multi-step reaction with 3 steps 1: dmap; dicyclohexyl-carbodiimide / dichloromethane 2: palladium on carbon; hydrogen / methanol / 20 °C 3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 °C
Reference： [1]Zhang, Bin; Zhang, Tangzhi; Sromek, Anna W.; Scrimale, Thomas; Bidlack, Jean M.; Neumeyer, John L. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 9, p. 2808 - 2816]
[2]Zhang, Bin; Zhang, Tangzhi; Sromek, Anna W.; Scrimale, Thomas; Bidlack, Jean M.; Neumeyer, John L. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 9, p. 2808 - 2816]
  • 20
  • [ 67852-88-4 ]
  • (5α)-17-allyl-14-hydroxy-6-oxo-4,5-epoxymorphinan-3-yl 14-methoxy-N-cyclobutylmethylmorphinan-3-yl decanedioate dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide 2: triethylamine / dichloromethane 3: palladium on carbon; hydrogen / methanol / 20 °C 4: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 °C 5: hydrogenchloride / diethyl ether; ethyl acetate
Multi-step reaction with 4 steps 1: dmap; dicyclohexyl-carbodiimide / dichloromethane 2: palladium on carbon; hydrogen / methanol / 20 °C 3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 °C 4: hydrogenchloride / diethyl ether; ethyl acetate
Reference： [1]Zhang, Bin; Zhang, Tangzhi; Sromek, Anna W.; Scrimale, Thomas; Bidlack, Jean M.; Neumeyer, John L. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 9, p. 2808 - 2816]
[2]Zhang, Bin; Zhang, Tangzhi; Sromek, Anna W.; Scrimale, Thomas; Bidlack, Jean M.; Neumeyer, John L. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 9, p. 2808 - 2816]
  • 21
  • [ 67852-88-4 ]
  • [ 42408-82-2 ]
  • [ 1310086-85-1 ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane 5.2.5. Benzyl (-)-14-methoxy-butorphanol-3-yl decanedioate (13b) General procedure: Method A: To the solution of sebacic acid monobenzyl ester (1.08 g, 3.53 mmol) in anhydrous CH2Cl2 (15 mL) was added oxalyl chloride (0.62 mL, 7.04 mmol) and two drops of DMF. Gas evolution could be observed and the solution was stirred overnight. Next, CH2Cl2 and excess oxalyl chloride was removed under reduced pressure. The yellow oil was redissolved in anhydrous CH2Cl2. 14-Methoxy-butorphanol (8) (1.00 g, 2.93 mmol) and Et3N (2.0 mL, 14.1 mmol) was added to the solution and the mixture was stirred overnight. The organic layer was washed with NaHCO3 solution and dried over Na2SO4. After solvent was removed under reduced pressure, the crude product was purified on silica gel (EtOAc/hexanes 1:4 and EtOAc/hexanes 1:1) to give a yellow oil (460 mg, 25%).Method B: To the solution of sebacic acid monobenzyl ester (206 mg, 0.676 mmol) and 14-methoxy-butorphanol (192 mg, 0.563 mmol) in anhydrous CH2Cl2 (6 mL) was added DCC (139 mg, 0.676 mmol), and DMAP (7 mg, 0.0563 mmol), and the reaction mixture was stirred overnight. The next day, after solvent was removed under reduced pressure, the residue was redissolved in an equal volume of ethyl acetate and the white solid was filtered off. The organic layer was washed with saturated NaHCO3 solution and brine, and dried over Na2SO4. The crude product was purified on silica gel (EtOAc/hexanes 1:1) to a give yellow oil (110 mg, 31%).
Reference： [1]Location in patent: experimental part Zhang, Bin; Zhang, Tangzhi; Sromek, Anna W.; Scrimale, Thomas; Bidlack, Jean M.; Neumeyer, John L. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 9, p. 2808 - 2816]
  • 22
  • [ 111-20-6 ]
  • [ 104-57-4 ]
  • [ 67852-88-4 ]
YieldReaction ConditionsOperation in experiment
With dowex 50W-X2 In octane at 80℃;
Reference： [1]Location in patent: body text Zhang, Xiao-Xiang; Prata, Carla A. H.; Berlin, Jason A.; McIntosh, Thomas J.; Barthelemy, Philippe; Grinstaff, Mark W. [Bioconjugate Chemistry, 2011, vol. 22, # 4, p. 690 - 699]
  • 23
  • [ 623-57-4 ]
  • [ 67852-88-4 ]
  • [ 1292292-56-8 ]
Reference： [1]Bioconjugate Chemistry,2011,vol. 22,p. 690 - 699
  • 24
  • [ 111-20-6 ]
  • [ 100-51-6 ]
  • [ 67852-88-4 ]
YieldReaction ConditionsOperation in experiment
47% With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;
42% Stage #1: 1,10-decanedioic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 1h; Stage #2: benzyl alcohol In dichloromethane at 0 - 25℃; for 16h; Synthesis of G-8 [0291] To a solution of decanedioic acid (100 g, 494.4 mmol, 1.00 equiv.) in dichloromethane (2000 mL), was added 4-dimethylaminopyridine (18.1 g, 148.2 mmol, 0.30 equiv.) at room temperature. To this was added N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (114 g, 594.7 mmol, 1.20 equiv.) at room temperature. The resulting solution was stirred for 1 h at room temperature. To the mixture was added Benzyl alcohol (64.1 g) dropwise with stirring at 0oC. The resulting solution was allowed to react, with stirring, overnight at room temperature. The resulting mixture was washed with saturated aqueous sodium chloride. The mixture was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product (100 g) was purified by Flash-Prep-HPLC with the following conditions (IntelFlash-1): Column, C18 silica gel; mobile phase, water and acetonitrile (60% acetonitrile up to 100% in 12 min and hold 100% for 5 min); Detector, UV 210 nm. This resulted in 60.7 g (42%) of G-8 as a white solid. MS m/z [M+H]+ (ESI): 293.
42% Stage #1: 1,10-decanedioic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 1h; Stage #2: benzyl alcohol In dichloromethane at 0 - 25℃; for 16h; Synthesis of G-8 To a solution of decanedioic acid (100 g, 494.4 mmol, 1.00 equiv.) in dichloromethane (2000 mL), was added 4-dimethylaminopyridine (18.1 g, 148.2 mmol, 0.30 equiv.) at room temperature. To this was added N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (114 g, 594.7 mmol, 1.20 equiv.) at room temperature. The resulting solution was stirred for 1 h at room temperature. To the mixture was added Benzyl alcohol (64.1 g) dropwise with stirring at 0°C. The resulting solution was allowed to react, with stirring, overnight at room temperature. The resulting mixture was washed with saturated aqueous sodium chloride. The mixture was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product (100 g) was purified by Flash-Prep-HPLC. This resulted in 60.7 g (42%) of G-8 as a white solid. MS m/z [M+H]+ (ESI): 293.
29% With toluene-4-sulfonic acid In toluene Dean-Stark; Reflux; Synthesis of monobenzyl sebacate (Supplementary material, Scheme S1) The method of English, Girard, Jasys, Martingano, and Kellogg (1990) was adapted for the synthesis of monobenzyl sebacate. Sebacic acid (0.25mol, 50.56g), toluene (200mL), benzyl alcohol (0.30mol, 1.2equiv., 32.4g, 31.1mL), and p-toluene sulfonic acid (2.5mmol, 0.475g) were combined in a Dean-Stark apparatus and refluxed until the desired volume of H2O (0.30mol, 5.40mL) was collected from the Fischer esterification of the sebacic acid, indicating the end of the reaction. The mixture was allowed to cool to room temperature, then 150mL of DI water was added to the reaction. Using vigorous mixing, this mixture was adjusted to pH 9 with 6M NaOH. The aqueous layer with the di-acid and mono-ester was separated and washed twice with 50mL of diethyl ether; these diethyl ether washes contained primarily the dibenzyl ester by-product, and were discarded. Diethyl ether (200mL) was combined with the aqueous layer which was acidified to pH of 2.0-2.5 with 6M HCl. The ether layer containing the mono-ester was separated. To purify further, the ether layer was washed with 1M NaHCO3. The ether layer then was concentrated under reduced pressure and vacuum-dried for 1.5h to yield the final product as white, needle-like solid. Yield: 29.0% (16.96g, 0.058mol).
29% With toluene-4-sulfonic acid In toluene Dean-Stark; Reflux; Synthesis of monobenzyl sebacate (Supplementary material,Scheme S1 ). General procedure: The method of English, Girard, Jasys, Martingano,and Kellogg (1990) was adapted for the synthesis of monobenzylsebacate. Sebacic acid (0.25 mol, 50.56 g), toluene (200 mL), benzylalcohol (0.30 mol, 1.2 equiv., 32.4 g, 31.1 mL), and p-toluene sulfonicacid (2.5 mmol, 0.475 g) were combined in a Dean-Stark apparatusand refluxed until the desired volume of H2O (0.30 mol, 5.40 mL)was collected from the Fischer esterification of the sebacic acid,indicating the end of the reaction. The mixture was allowed to coolto room temperature, then 150 mL of DI water was added to thereaction. Using vigorous mixing, this mixture was adjusted to pH 9with 6 M NaOH. The aqueous layer with the di-acid and mono-esterwas separated and washed twice with 50 mL ofdiethyl ether; thesediethyl ether washes contained primarily the dibenzyl ester byproduct, and were discarded. Diethyl ether (200 mL) was combinedwith the aqueous layer which was acidified to pH of 2.0-2.5 with6 M HCl. The ether layer containing the mono-ester was separated.To purify further, the ether layer was washed with 1 M NaHCO3.The ether layer then was concentrated under reduced pressure andvacuum-dried for 1.5 h to yield the final product as white, needlelike solid. Yield: 29.0% (16.96 g, 0.058 mol). 1 H NMR (CDCl3): 1.29(m, 8H), 1.62 (m, 4H), 2.33 (m, 4H), 5.11 (s, 2H), 7.35 (m, 5H).

Reference： [1]Location in patent: experimental part Birnkammer, Tobias; Spickenreither, Anja; Brunskole, Irena; Lopuch, Miroslaw; Kagermeier, Nicole; Bernhardt, Günther; Dove, Stefan; Seifert, Roland; Elz, Sigurd; Buschauer, Armin [Journal of Medicinal Chemistry, 2012, vol. 55, # 3, p. 1147 - 1160]
[2]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2018/53185, 2018, A1 Location in patent: Paragraph 0291
[3]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2019/53661, 2019, A2 Location in patent: Paragraph 0107
[4]Liu, Haoyu; Ilevbare, Grace A.; Cherniawski, Benjamin P.; Ritchie, Earl T.; Taylor, Lynne S.; Edgar, Kevin J. [Carbohydrate Polymers, 2014, vol. 100, p. 116 - 125]
[5]Liu, Haoyu; Ilevbare, Grace A.; Cherniawski, Benjamin P.; Ritchie, Earl T.; Taylor, Lynne S.; Edgar, Kevin J. [Carbohydrate Polymers, 2014, vol. 100, p. 116 - 125]
  • 25
  • [ 1151467-61-6 ]
  • [ 67852-88-4 ]
  • C35H53N5O7S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h;
Reference： [1]Location in patent: experimental part Birnkammer, Tobias; Spickenreither, Anja; Brunskole, Irena; Lopuch, Miroslaw; Kagermeier, Nicole; Bernhardt, Günther; Dove, Stefan; Seifert, Roland; Elz, Sigurd; Buschauer, Armin [Journal of Medicinal Chemistry, 2012, vol. 55, # 3, p. 1147 - 1160]
  • 26
  • [ 111-19-3 ]
  • [ 100-51-6 ]
  • [ 67852-88-4 ]
YieldReaction ConditionsOperation in experiment
57% With triethylamine In diethyl ether at -78 - 20℃; Inert atmosphere;
Reference： [1]Location in patent: experimental part Moser, Ralph; Ghorai, Subir; Lipshutz, Bruce H. [Journal of Organic Chemistry, 2012, vol. 77, # 7, p. 3143 - 3148]
  • 27
  • [ 67852-88-4 ]
  • fumagillol [ No CAS ]
  • [ 1399361-15-9 ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: decanedioic acid monobenzyl ester With oxalyl dichloride In dichloromethane at 20℃; for 2h; Stage #2: fumagillol In dichloromethane at 20℃; 9 Example 9 [0135] O.lg (0.34 mmol) of Sebacic acid mono benzyl ester is dissolved in 4 mL of dry CH2CL2. Then 0.06mL (0.71mmol) of oxallyl chloride is added followed by 2 drops of DMF. Gas evolution is observed and the reaction is allowed to go for 2h at room temperature. The solvent and excess oxallyl chloride is removed in vacuo and the resulting yellow oil is dissolved in 4mL of dry CH2CL2. Fumagillol (0.97g, 3.4 mmol) is added followed by DMAP (0.087g, 0.68 mmol) and the reaction is allowed to stir overnight at room temperature. In the morning the reaction is diluted with 50mL of and washed with 2x lOOmL of saturatedNaHCOs, 2x lOOmL of water, and dried over Na2S04. Purification by biotage flashchromatography (Si02, EtOAc/Hexanes gradient) affords 0.145g (76%) of Intermediate D.
Reference： [1]Current Patent Assignee: LARIMAR THERAPEUTICS INC - WO2012/122264, 2012, A1 Location in patent: Page/Page column 53
  • 28
  • [ 67852-88-4 ]
  • fumagillol [ No CAS ]
  • [ 907571-53-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 1.2: 20 °C 2.1: hydrogen / palladium 10% on activated carbon / ethanol / 0.33 h / Inert atmosphere
Reference： [1]Current Patent Assignee: LARIMAR THERAPEUTICS INC - WO2012/122264, 2012, A1
  • 29
  • [ 111-20-6 ]
  • [ 100-39-0 ]
  • [ 67852-88-4 ]
YieldReaction ConditionsOperation in experiment
66% With tetrabutylammonium bromide; potassium hydroxide In methanol Inert atmosphere; Octanedioic Acid Monobenzyl Ester [PhCH2O2C(CH2)6CO2H] General procedure: This compound was prepared as described for PhCH2O2C(CH2)12CO2H.18Octanedioic acid (2.92 g, 16.8 mmol), 10% KOH (1.00 g, 17.8mmol) in MeOH, TBAB (0.56 g, 1.7 mmol), and PhCH2Br (2.86mL, 24.1 mmol) afforded a white solid; yield: 2.88 g (65%). Thespectroscopic properties were identical to those previously published.20
42% With Sodium hydrogenocarbonate In 1,4-dioxane; N,N-dimethyl-formamide at 90℃;
Reference： [1]Curvey, Nichole S.; Luderer, Sarah E.; Walker, John K.; Gokel, George W. [Synthesis, 2014, vol. 46, # 20, p. 2771 - 2779]
[2]Baker, India M.; Bowman, Karen J.; Cowley, Shaun M.; Hodgkinson, James T.; Lin, Li-Ying; Pytel, Wiktoria A.; Schwabe, John W. R.; Smalley, Joshua P. [Journal of Medicinal Chemistry, 2022, vol. 65, # 7, p. 5642 - 5659]
  • 30
  • [ 67852-88-4 ]
  • C32H58N2O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C / Inert atmosphere 1.2: 18 h / 20 °C / Inert atmosphere 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 18 h / 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine 2: palladium 10% on activated carbon
Reference： [1]Curvey, Nichole S.; Luderer, Sarah E.; Walker, John K.; Gokel, George W. [Synthesis, 2014, vol. 46, # 20, p. 2771 - 2779]
[2]Current Patent Assignee: UNIVERSITY OF MISSOURI SYSTEM - WO2016/22991, 2016, A1
  • 31
  • [ 67852-88-4 ]
  • [ 23978-55-4 ]
  • PhCH2OCO(CH2)8CON18NCO(CH2)8CO2CH2Ph [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% General procedure: A mixture of octanedioic acid monobenzyl ester (1.87 g, 7.09mmol), HBTU (2.70 g, 7.12 mmol), and DIPEA (7.31 mL, 42.0mmol) in CH2Cl2 (50 mL) was stirred at r.t. for 10 min. Diaza-18-crown-6 (2; 0.837 g, 3.19 mmol) was added in one portion and the mixture was allowed to stir at r.t. for 18 h. The reaction mixture was washed with H2O (3 × 50 mL) and dried (MgSO4); chromatography (silica gel; MeOH-CHCl3, 0:100 to 10:90) afforded a yellow oil; yield: 2.22 g (92%).
90% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; [0107] PhCH2OCO(CH2)8C0 CO(CH2)8CO2CH2Ph. This compound was prepared similarly to PhCH2OCO(CH2)6C0CO(CH2)6CO2CH2Ph. Decanedioic acid monobenzyl ester (2.23 g, 7.62 mmol), HBTU (2.89 g, 7.62 mmol), Et(i-Pr)2N (7.85 mL, 45.1 mmol), and diaza-18-crown-6 (0.900 g, 3.43 mmol) afforded a colorless oil (2.50 g, 90%). 1H-NMR: 0.99 (16H, bs), 1.31 (8H, bs), 2.03 (8H, m), 3.18-3.36 (24H, m), 6.89-7.07 (1OH, m). 13C-NMR: 24.11, 24.49, 28.22, 28.32, 28.50, 28.53, 32.19, 33.33, 37.73, 46.21, 46.29, 48.03, 48.11, 65.02,68.94, 69.07, 69.32, 69.63, 69.77, 69.91, 70.04, 127.27, 127.69, 135.49, 172.25, 172.27, 172.39.
Reference： [1]Synthesis,2014,vol. 46,p. 2771 - 2779
[2]Patent: WO2016/22991,2016,A1 .Location in patent: Paragraph 0107
  • 32
  • [ 693-23-2 ]
  • [ 100-39-0 ]
  • [ 67852-88-4 ]
YieldReaction ConditionsOperation in experiment
66% With tetrabutylammomium bromide; potassium hydroxide In methanol 7 PhCH2OCO(CH2)8COOH (decanedioic acid monobenzyl ester). [0106] PhCH2OCO(CH2)8COOH (decanedioic acid monobenzyl ester). This compound was prepared similarly to PhCH2OCO(CH2)6COOH. Dodecanedioic acid (2.90 g, 14.3 mmol), 10% KOH (0.85 g, 15.1 mmol) in MeOH, Bu4NBr (0.48 g, 1.49 mmol), and PhCH2Br (2.47 mL, 20.8 mmol) afforded a white solid (2.76 g, 66%).
Reference： [1]Current Patent Assignee: UNIVERSITY OF MISSOURI SYSTEM - WO2016/22991, 2016, A1 Location in patent: Paragraph 0106
  • 33
  • C79H128N10O36 [ No CAS ]
  • [ 67852-88-4 ]
  • C96H150N10O39 [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% Stage #1: 10-(benzyloxy)-10-oxodecanoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 25℃; for 1h; Stage #2: C79H128N10O36 In acetonitrile at 25℃; for 16h; Synthesis of G-10 [0292] To a solution of G-8 (4.48 g, 15.32 mmol, 1.50 equiv.) in acetonitrile (320 mL) was added O-Benzotriazole-N,N,N-etramethyl-uronium-hexafluorophosphate (5.84 g, 15.40 mmol, 1.50 equiv.), N,N-Diisopropylethylamine (3.96 g, 30.64 mmol, 3.00 equiv.). The resulting solution was stirred for 1 h at 25oC. This was followed by the addition of G-9 (18.4 g, 10.26 mmol, 1.00 equiv.). The resulting solution was stirred for 16 h at 25 oC, and then concentrated under vacuum. The crude product was purified by Flash with the following conditions: Column, C18 silica gel; mobile phase, acetonitrile in water = 10% increasing to 70% within 15 min; Detector, UV 210 nm. This resulted in 12 g (57%) of G-10 as a white solid. H-NMR (DMSO, 400MHz, ppm): 7.74-7.83 (m, 9H), 7.31-7.37 (m, 5H), 6.97 (s, 1H), 5.21 (d, J = 3.3 Hz, 3H), 5.07 (s, 2H), 4.98 (dd, J = 11.2 Hz, 3.4 Hz, 3H), 4.49 (d, J = 8.4 Hz, 3H), 4.04 (s, 9H), 3.83-3.99 (m, 3H), 3.67-3.72 (m, 3H), 3.52-3.55 (m, 12H), 3.37-3.43 (m, 3H), 2.99-3.05 (m, 12H), 2.25- 2.35 (m, 8H), 2.12 (s, 9H), 1.99-2.11 (m, 17H), 1.92 (s, 9H), 1.77 (s, 9H), 1.40-1.53 (m, 22H), 1.19-1.25 (m, 8H).
57% Stage #1: 10-(benzyloxy)-10-oxodecanoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 25℃; for 1h; Stage #2: C79H128N10O36 In acetonitrile at 25℃; for 16h; Synthesis of G-10 To a solution of G-8 (4.48 g, 15.32 mmol, 1.50 equiv.) in acetonitrile (320 mL) was added 0-Benzotriazole-N,N,N-etramethyl-uronium-hexafluorophosphate (5.84 g, 15.40 mmol, 1.50 equiv.), N,N-Diisopropylethylamine (3.96 g, 30.64 mmol, 3.00 equiv.). The resulting solution was stirred for 1 h at 25°C. This was followed by the addition of G-9 (18.4 g, 10.26 mmol, 1.00 equiv.). The resulting solution was stirred for 16 h at 25 °C, and then concentrated under vacuum. The crude product was purified by Flash. This resulted in 12 g (57%) of G-10 as a white solid. H-NMR (DMSO, 400MHz, ppm): 7.74-7.83 (m, 9H), 7.31-7.37 (m, 5H), 6.97 (s, 1H), 5.21 (d, J= 3.3 Hz, 3H), 5.07 (s, 2H), 4.98 (dd, J= 11.2 Hz, 3.4 Hz, 3H), 4.49 (d, J= 8.4 Hz, 3H), 4.04 (s, 9H), 3.83-3.99 (m, 3H), 3.67-3.72 (m, 3H), 3.52-3.55 (m, 12H), 3.37-3.43 (m, 3H), 2.99-3.05 (m, 12H), 2.25-2.35 (m, 8H), 2.12 (s, 9H), 1.99-2.11 (m, 17H), 1.92 (s, 9H), 1.77 (s, 9H), 1.40-1.53 (m, 22H), 1.19-1.25 (m, 8H).
Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2018/53185, 2018, A1 Location in patent: Paragraph 0292
[2]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2019/53661, 2019, A2 Location in patent: Paragraph 0108
  • 34
  • 20-hydroxyecdysone 2,3;20,22-di(cyclohexylacetal) [ No CAS ]
  • [ 67852-88-4 ]
  • C56H82O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 96h;
Reference： [1]Fumagalli, Gaia; Giorgi, Giulia; Vágvölgyi, Máté; Colombo, Eleonora; Christodoulou, Michael S.; Collico, Veronica; Prosperi, Davide; Dosio, Franco; Hunyadi, Attila; Montopoli, Monica; Hyeraci, Mariafrancesca; Silvani, Alessandra; Lesma, Giordano; Via, Lisa Dalla; Passarella, Daniele [ACS Medicinal Chemistry Letters, 2018, vol. 9, # 5, p. 468 - 471]
  • 35
  • [ 67852-88-4 ]
  • 20-hydroxyecdysone 2,3:20,22-diacetonide [ No CAS ]
  • C50H74O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 30h;
Reference： [1]Fumagalli, Gaia; Giorgi, Giulia; Vágvölgyi, Máté; Colombo, Eleonora; Christodoulou, Michael S.; Collico, Veronica; Prosperi, Davide; Dosio, Franco; Hunyadi, Attila; Montopoli, Monica; Hyeraci, Mariafrancesca; Silvani, Alessandra; Lesma, Giordano; Via, Lisa Dalla; Passarella, Daniele [ACS Medicinal Chemistry Letters, 2018, vol. 9, # 5, p. 468 - 471]
  • 36
  • [ 67852-88-4 ]
  • C43H68O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 30 h / 0 - 20 °C 2: hydrogen; 10 wt% Pd(OH)2 on carbon / ethyl acetate / 2 h / 20 °C
Reference： [1]Fumagalli, Gaia; Giorgi, Giulia; Vágvölgyi, Máté; Colombo, Eleonora; Christodoulou, Michael S.; Collico, Veronica; Prosperi, Davide; Dosio, Franco; Hunyadi, Attila; Montopoli, Monica; Hyeraci, Mariafrancesca; Silvani, Alessandra; Lesma, Giordano; Via, Lisa Dalla; Passarella, Daniele [ACS Medicinal Chemistry Letters, 2018, vol. 9, # 5, p. 468 - 471]
  • 37
  • [ 2561-88-8 ]
  • [ 100-51-6 ]
  • [ 67852-88-4 ]
YieldReaction ConditionsOperation in experiment
57% With pyridine In dichloromethane at 20℃; for 72h; 1 Alternate procedure (larger scale) A mixture of sebacic acid (100 g, 495 mmol) and acetyl chloride (250 mL, 3.53 mol) was heated under reflux for 16 h, then cooled and concentrated to dryness. It was added into a solution of pyridine (270 g, 3.4 mol) and benzyl alcohol (100 g, 926 mmol) in dichloromethane (1500 mL) at room temperature and the mixture was stirred for 72 h. The reaction was concentrated and the residue was purified by column chromatography, eluting with from 0 to 50% ethyl acetate in petroleum ether to afford mt-li (82 g, 281 mmol, 57% yield) as a yellowish oil. LC-MS: MS m/z = 293 (M+ H+), RT = 1.45 mm.
57% With pyridine In dichloromethane at 20℃; for 72h; 1 Alternate procedure (larger scale): A mixture of sebacic acid (100 g, 495 mmol) and acetyl chloride (250 mL, 3.53 mol) was heated under reflux for 16 h, then cooled and concentrated to dryness. It was added into a solution of pyridine (270 g, 3.4 mol) and benzyl alcohol (100 g, 926 mmol) in dichloromethane (1500 mL) at room temperature and the mixture was stirred for 72 h. The reaction was concentrated and the residue was purified by column chromatography, eluting with from 0 to 50% ethyl acetate in petroleum ether to afford Int-11 (82 g, 281 mmol, 57% yield) as a yellowish oil. LC-MS: MS m/z = 293 (M+ H+), RT = 1.45 min.
82 g With pyridine In dichloromethane at 20℃; for 72h; 1 A mixture of sebacic acid (100 g, 495 mmol) and acetyl chloride (250 mL, 3.53 mol) was heated under reflux for 16 h, then cooled and concentrated to dryness. It was added into a solution of pyridine (270 g, 3.4 mol) and benzyl alcohol (100 g, 926 mmol) in dichloromethane (1500 mL) at room temperature and the mixture was stirred for 72 h. The reaction was concentrated and the residue was purified by column chromatography, eluting with from 0 to 50% ethyl acetate in petroleum ether to afford Int-11 (82 g, 281 mmol, 57% yield) as a yellowish oil. LC-MS: MS m/z = 293 (M+ H+), RT = 1.45 min.
82 g With pyridine In dichloromethane at 20℃; for 72h; 1 A mixture of sebacic acid (100 g, 495 mmol) and acetyl chloride (250 mL, 3.53 mol) was heated under reflux for 16 h, then cooled and concentrated to dryness. It was added into a solution of pyridine (270 g, 3.4 mol) and benzyl alcohol (100 g, 926 mmol) in dichloromethane (1500 mL) at room temperature and the mixture was stirred for 72 h. The reaction was concentrated and the residue was purified by column chromatography, eluting with from 0 to 50% ethyl acetate in petroleum ether to afford lnt-11 (82 g, 281 mmol, 57% yield) as a yellowish oil. LC-MS: MS m/z = 293 (M+ H+), RT = 1.45 min.
82 g With pyridine In dichloromethane at 20℃; for 72h; [00408] A mixture of sebacic acid (100 g, 495 mmol) and acetyl chloride (250 mL, 3.53 mol) was heated under reflux for 16 h, then cooled and concentrated to dryness. It was added into a solution of pyridine (270 g, 3.4 mol) and benzyl alcohol (100 g, 926 mmol) in dichloromethane (1500 mL) at room temperature and the mixture was stirred for 72 h. The reaction was concentrated and the residue was purified by column chromatography, eluting with from 0 to 50% ethyl acetate in petroleum ether to afford lnt-11 (82 g, 281 mmol, 57% yield) as a yellowish oil. LC-MS: MS m/z = 293 (M+ H+), RT = 1.45 min.
With dmap; triethylamine In dichloromethane at 20℃; for 8h;
82 g With pyridine In dichloromethane at 20℃; for 72h; 1 [00341] Alternate procedure (larger scale): [00342] A mixture of sebacic acid (100 g, 495 mmol) and acetyl chloride (250 mL, 3.53 mol) was heated under reflux for 16 h, then cooled and concentrated to dryness. It was added into a solution of pyridine (270 g, 3.4 mol) and benzyl alcohol (100 g, 926 mmol) in dichloromethane (1500 mL) at room temperature and the mixture was stirred for 72 h. The reaction was concentrated and the residue was purified by column chromatography, eluting with from 0 to 50% ethyl acetate in petroleum ether to afford Int-11 (82 g, 281 mmol, 57% yield) as a yellowish oil. LC-MS: MS m/z = 293 (M+ H+), RT = 1.45 min.
82 g With pyridine In dichloromethane at 20℃; for 72h; 1 [00341] Alternate procedure (larger scale): [00342] A mixture of sebacic acid (100 g, 495 mmol) and acetyl chloride (250 mL, 3.53 mol) was heated under reflux for 16 h, then cooled and concentrated to dryness. It was added into a solution of pyridine (270 g, 3.4 mol) and benzyl alcohol (100 g, 926 mmol) in dichloromethane (1500 mL) at room temperature and the mixture was stirred for 72 h. The reaction was concentrated and the residue was purified by column chromatography, eluting with from 0 to 50% ethyl acetate in petroleum ether to afford Int-11 (82 g, 281 mmol, 57% yield) as a yellowish oil. LC-MS: MS m/z = 293 (M+ H+), RT = 1.45 min.

Reference： [1]Current Patent Assignee: PURETECH HEALTH PLC; MONASH UNIVERSITY - WO2019/46491, 2019, A1 Location in patent: Paragraph 00430; 004311
[2]Current Patent Assignee: PURETECH HEALTH PLC - WO2020/176859, 2020, A1 Location in patent: Paragraph 00414-00415
[3]Current Patent Assignee: PURETECH HEALTH PLC - WO2020/28787, 2020, A1 Location in patent: Paragraph 00295; 00296
[4]Current Patent Assignee: PURETECH HEALTH PLC; MONASH UNIVERSITY - WO2020/176868, 2020, A1 Location in patent: Paragraph 00405; 00423; 00424
[5]Current Patent Assignee: MONASH UNIVERSITY; PURETECH HEALTH PLC - WO2020/176856, 2020, A1 Location in patent: Paragraph 00407; 00408
[6]Li, Jia; Lu, Wei; Lu, Yingxin; Shao, Yingying; Su, Mingbo; Sun, Danwen; Xiao, Donghuai; Zhou, Yubo; Zhu, Shulei [Molecules, 2021, vol. 26, # 23]
[7]Current Patent Assignee: MONASH UNIVERSITY; PURETECH HEALTH PLC - WO2021/159021, 2021, A1 Location in patent: Paragraph 00341-00342
[8]Current Patent Assignee: MONASH UNIVERSITY; PURETECH HEALTH PLC - WO2021/159021, 2021, A1 Location in patent: Paragraph 00341-00342
  • 38
  • [ 111-20-6 ]
  • [ 67852-88-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetyl chloride / 16 h / Reflux 2: pyridine / dichloromethane / 72 h / 20 °C
Multi-step reaction with 2 steps 1: acetyl chloride / 16 h / Reflux 2: pyridine / dichloromethane / 72 h / 20 °C
Multi-step reaction with 2 steps 1: acetic anhydride / 12 h / Reflux 2: triethylamine; dmap / dichloromethane / 8 h / 20 °C
Reference： [1]Current Patent Assignee: PURETECH HEALTH PLC; MONASH UNIVERSITY - WO2019/46491, 2019, A1 Current Patent Assignee: MONASH UNIVERSITY; PURETECH HEALTH PLC - WO2020/176856, 2020, A1
[2]Current Patent Assignee: PURETECH HEALTH PLC - WO2020/28787, 2020, A1 Current Patent Assignee: PURETECH HEALTH PLC - WO2020/176859, 2020, A1 Current Patent Assignee: PURETECH HEALTH PLC; MONASH UNIVERSITY - WO2020/176868, 2020, A1 Current Patent Assignee: MONASH UNIVERSITY; PURETECH HEALTH PLC - WO2021/159021, 2021, A1
[3]Li, Jia; Lu, Wei; Lu, Yingxin; Shao, Yingying; Su, Mingbo; Sun, Danwen; Xiao, Donghuai; Zhou, Yubo; Zhu, Shulei [Molecules, 2021, vol. 26, # 23]
  • 39
  • [ 67852-88-4 ]
  • C45H84O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; triethylamine / dichloromethane / 72 h / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / tetrahydrofuran / 16 h / 30 °C
Multi-step reaction with 2 steps 1: triethylamine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 72 h / 0 - 20 °C 2: hydrogen; palladium on activated charcoal / tetrahydrofuran / 16 h / 30 °C
Reference： [1]Current Patent Assignee: PURETECH HEALTH PLC; MONASH UNIVERSITY - WO2019/46491, 2019, A1 Current Patent Assignee: PURETECH HEALTH PLC - WO2020/28787, 2020, A1 Current Patent Assignee: MONASH UNIVERSITY; PURETECH HEALTH PLC - WO2020/176856, 2020, A1 Current Patent Assignee: PURETECH HEALTH PLC - WO2020/176859, 2020, A1 Current Patent Assignee: PURETECH HEALTH PLC; MONASH UNIVERSITY - WO2020/176868, 2020, A1
[2]Current Patent Assignee: MONASH UNIVERSITY; PURETECH HEALTH PLC - WO2021/159021, 2021, A1
  • 40
  • [ 502-52-3 ]
  • [ 67852-88-4 ]
  • C52H90O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; for 72h; 1 To a mixture of mt-li (82 g, 281 mmol) and Int-2 (1,3-DG) (80 g, 140 mmol) in dichloromethane (1500 mL) was added EDCI (115 g, 600 mmol) and DMAP (3.66 g, 30 mmol). Then triethylamine (100 mL, 719 mmol) was added dropwise at 0 °C. The mixture was stirred at room temperature for 72 h. The reaction was concentrated to dryness and the residue was purified by column chromatography, eluting with ethyl acetate in petroleum ether from 0 to 50% to afford Int-12 (65 g, 77 mmol, 27% yield) as a white solid. ‘H NMR (400 MHz, chloroform-d) 7.3 8- 7.29 (m, 5H), 5.27-5.25 (m, 1H), 5.11 (s, 2H), 4.3 1-4.27 (m, 2H), 4.17-4.12 (m, 2H), 2.37-2.29 (m, 8H), 1.65-1.57 (m, 8H), 1.35-1.20 (m, 56H), 0.88 (t, J= 6.6 Hz, 6H).
27% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; for 72h; 1 To a mixture of Int-11 (82 g, 281 mmol) and Int-2 (1,3-DG) (80 g, 140 mmol) in dichloromethane (1500 mL) was added EDCI (115 g, 600 mmol) and DMAP (3.66 g, 30 mmol). Then triethylamine (100 mL 719 mmol) was added dropwise at 0 C The mixture was stirred at room temperature for 72 h. The reaction was concentrated to dryness and the residue was purified by column chromatography, eluting with ethyl acetate in petroleum ether from 0 to 50% to afford Int-12 (65 g, 77 mmol, 27% yield) as a white solid. 1H NMR (400 MHz, chloroform-d) d 7.38-7.29 (m, 5H), 5.27-5.25 (m, 1H), 5.11 (s, 2H), 4.31-4.27 (m, 2H), 4.17-4.12 (m, 2H), 2.37-2.29 (m, 8H), 1.65-1.57 (m, 8H), 1.35-1.20 (m, 56H), 0.88 (t, J = 6.6 Hz, 6H).
27% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; for 72h; 1 To a mixture of Int-11 (82 g, 281 mmol) and Int-2 (1,3-DG) (80 g, 140 mmol) in dichloromethane (1500 mL) was added EDCI (115 g, 600 mmol) and DMAP (3.66 g, 30 mmol). Then triethylamine (100 mL, 719 mmol) was added dropwise at 0 C. The mixture was stirred at room temperature for 72 h. The reaction was concentrated to dryness and the residue was purified by column chromatography, eluting with ethyl acetate in petroleum ether from 0 to 50% to afford Int-12 (65 g, 77 mmol, 27% yield) as a white solid. 1H NMR (400 MHz, chloroform-d) d 7.38- 7.29 (m, 5H), 5.27-5.25 (m, 1H), 5.11 (s, 2H), 4.31-4.27 (m, 2H), 4.17-4.12 (m, 2H), 2.37-2.29 (m, 8H), 1.65-1.57 (m, 8H), 1.35-1.20 (m, 56H), 0.88 (t, J = 6.6 Hz, 6H).
27% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; for 72h; 1 To a mixture of lnt-11 (82 g, 281 mmol) and Int-2 (1,3-DG) (80 g, 140 mmol) in dichloromethane (1500 mL) was added EDCI (115 g, 600 mmol) and DMAP (3.66 g, 30 mmol). Then triethylamine (100 mL, 719 mmol) was added dropwise at 0 °C. The mixture was stirred at room temperature for 72 h. The reaction was concentrated to dryness and the residue was purified by column chromatography, eluting with ethyl acetate in petroleum ether from 0 to 50% to afford Int-12 (65 g, 77 mmol, 27% yield) as a white solid. NMR (400 MHz, chloroform-d) d 7.38- 7.29 (m, 5H), 5.27-5.25 (m, 1H), 5.11 (s, 2H), 4.31-4.27 (m, 2H), 4.17-4.12 (m, 2H), 2.37-2.29 (m, 8H), 1.65-1.57 (m, 8H), 1.35-1.20 (m, 56H), 0.88 (t, J= 6.6 Hz, 6H).
27% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; for 72h; [00409] To a mixture of lnt-11 (82 g, 281 mmol) and Int-2 (1,3-DG) (80 g, 140 mmol) in dichloromethane (1500 mL) was added EDCI (115 g, 600 mmol) and DMAP (3.66 g, 30 mmol). Then triethylamine (100 mL, 719 mmol) was added dropwise at 0 °C. The mixture was stirred at room temperature for 72 h. The reaction was concentrated to dryness and the residue was purified by column chromatography, eluting with ethyl acetate in petroleum ether from 0 to 50% to afford Int-12 (65 g, 77 mmol, 27% yield) as a white solid. NMR (400 MHz, chloroform-d) d 7.38- 7.29 (m, 5H), 5.27-5.25 (m, 1H), 5.11 (s, 2H), 4.31-4.27 (m, 2H), 4.17-4.12 (m, 2H), 2.37-2.29 (m, 8H), 1.65-1.57 (m, 8H), 1.35-1.20 (m, 56H), 0.88 (t, J= 6.6 Hz, 6H).
27% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; for 72h; 1 [00343] To a mixture of Int-11 (82 g, 281 mmol) and Int-2 (1,3-DG) (80 g, 140 mmol) in dichloromethane (1500 mL) was added EDCI (115 g, 600 mmol) and DMAP (3.66 g, 30 mmol). Then triethylamine (100 mL, 719 mmol) was added dropwise at 0°C. The mixture was stirred at room temperature for 72 h. The reaction was concentrated to dryness and the residue was purified by column chromatography, eluting with ethyl acetate in petroleum ether from 0 to 50% to afford Int-12 (65 g, 77 mmol, 27% yield) as a white solid. 1H NMR (400 MHz, chloroform-d) δ 7.38-7.29 (m, 5H), 5.27-5.25 (m, 1H), 5.11 (s, 2H), 4.31-4.27 (m, 2H), 4.17-4.12 (m, 2H), 2.37-2.29 (m, 8H), 1.65-1.57 (m, 8H), 1.35-1.20 (m, 56H), 0.88 (t, J = 6.6 Hz, 6H).
27% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; for 72h; 1 [00343] To a mixture of Int-11 (82 g, 281 mmol) and Int-2 (1,3-DG) (80 g, 140 mmol) in dichloromethane (1500 mL) was added EDCI (115 g, 600 mmol) and DMAP (3.66 g, 30 mmol). Then triethylamine (100 mL, 719 mmol) was added dropwise at 0°C. The mixture was stirred at room temperature for 72 h. The reaction was concentrated to dryness and the residue was purified by column chromatography, eluting with ethyl acetate in petroleum ether from 0 to 50% to afford Int-12 (65 g, 77 mmol, 27% yield) as a white solid. 1H NMR (400 MHz, chloroform-d) δ 7.38-7.29 (m, 5H), 5.27-5.25 (m, 1H), 5.11 (s, 2H), 4.31-4.27 (m, 2H), 4.17-4.12 (m, 2H), 2.37-2.29 (m, 8H), 1.65-1.57 (m, 8H), 1.35-1.20 (m, 56H), 0.88 (t, J = 6.6 Hz, 6H).

Reference： [1]Current Patent Assignee: PURETECH HEALTH PLC; MONASH UNIVERSITY - WO2019/46491, 2019, A1 Location in patent: Paragraph 00430; 00432
[2]Current Patent Assignee: PURETECH HEALTH PLC - WO2020/28787, 2020, A1 Location in patent: Paragraph 00295; 00297
[3]Current Patent Assignee: PURETECH HEALTH PLC - WO2020/176859, 2020, A1 Location in patent: Paragraph 00414; 00416
[4]Current Patent Assignee: PURETECH HEALTH PLC; MONASH UNIVERSITY - WO2020/176868, 2020, A1 Location in patent: Paragraph 00405; 00423; 00425
[5]Current Patent Assignee: MONASH UNIVERSITY; PURETECH HEALTH PLC - WO2020/176856, 2020, A1 Location in patent: Paragraph 00407; 00409
[6]Current Patent Assignee: MONASH UNIVERSITY; PURETECH HEALTH PLC - WO2021/159021, 2021, A1 Location in patent: Paragraph 00341; 00343
[7]Current Patent Assignee: MONASH UNIVERSITY; PURETECH HEALTH PLC - WO2021/159021, 2021, A1 Location in patent: Paragraph 00341; 00343
  • 41
  • [ 67852-88-4 ]
  • C47H87ClO8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; triethylamine / dichloromethane / 72 h / 0 - 20 °C 2.1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 16 h / 30 °C 3.1: thionyl chloride; N,N-dimethyl-formamide / 1.25 h / Reflux 4.1: zirconium(IV) chloride / dichloromethane / 0.17 h / 0 °C 4.2: 1.5 h / 0 - 20 °C
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; triethylamine / dichloromethane / 72 h / 0 - 20 °C 2.1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 16 h / 30 °C 3.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 1.25 h / Reflux 4.1: zirconium(IV) chloride / dichloromethane / 0.17 h / 0 °C 4.2: 1.5 h / 0 - 20 °C
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; triethylamine / dichloromethane / 72 h / 0 - 20 °C 2.1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 16 h / 30 °C 3.1: N,N-dimethyl-formamide; thionyl chloride / 1.25 h / Reflux 4.1: zirconium(IV) chloride / dichloromethane / 0.17 h / 0 °C 4.2: 1.5 h / 0 - 20 °C
Reference： [1]Current Patent Assignee: PURETECH HEALTH PLC - WO2020/28787, 2020, A1 Current Patent Assignee: PURETECH HEALTH PLC; MONASH UNIVERSITY - WO2020/176868, 2020, A1
[2]Current Patent Assignee: PURETECH HEALTH PLC - WO2020/176859, 2020, A1
[3]Current Patent Assignee: MONASH UNIVERSITY; PURETECH HEALTH PLC - WO2020/176856, 2020, A1
  • 42
  • [ 67852-88-4 ]
  • C58H100O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; triethylamine / dichloromethane / 72 h / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / tetrahydrofuran / 16 h / 30 °C 3: potassium carbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 18 h / 100 °C
Multi-step reaction with 3 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; triethylamine / dichloromethane / 72 h / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / tetrahydrofuran / 16 h / 30 °C 3: potassium carbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 18 h / 20 - 100 °C
Multi-step reaction with 3 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; triethylamine / dichloromethane / 72 h / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / tetrahydrofuran / 16 h / 30 °C 3: tetra-(n-butyl)ammonium iodide; potassium carbonate / N,N-dimethyl-formamide / 18 h / 20 - 100 °C
Multi-step reaction with 3 steps 1: triethylamine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 72 h / 0 - 20 °C 2: hydrogen; palladium on activated charcoal / tetrahydrofuran / 16 h / 30 °C 3: potassium carbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 18 h / 100 °C

Reference： [1]Current Patent Assignee: PURETECH HEALTH PLC - WO2020/28787, 2020, A1 Current Patent Assignee: PURETECH HEALTH PLC; MONASH UNIVERSITY - WO2020/176868, 2020, A1
[2]Current Patent Assignee: PURETECH HEALTH PLC - WO2020/176859, 2020, A1
[3]Current Patent Assignee: MONASH UNIVERSITY; PURETECH HEALTH PLC - WO2020/176856, 2020, A1
[4]Current Patent Assignee: MONASH UNIVERSITY; PURETECH HEALTH PLC - WO2021/159021, 2021, A1
  • 43
  • [ 67852-88-4 ]
  • C50H92O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; triethylamine / dichloromethane / 72 h / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / tetrahydrofuran / 16 h / 30 °C 3: potassium carbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 18 h / 100 °C 4: hydrogen; palladium 10% on activated carbon / ethyl acetate / 16 h / 20 °C / 5171.62 Torr / Autoclave
Multi-step reaction with 4 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; triethylamine / dichloromethane / 72 h / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / tetrahydrofuran / 16 h / 30 °C 3: potassium carbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 18 h / 20 - 100 °C 4: palladium 10% on activated carbon; hydrogen / ethyl acetate / 16 h / 20 °C / 5171.62 Torr / Autoclave
Multi-step reaction with 4 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; triethylamine / dichloromethane / 72 h / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / tetrahydrofuran / 16 h / 30 °C 3: tetra-(n-butyl)ammonium iodide; potassium carbonate / N,N-dimethyl-formamide / 18 h / 20 - 100 °C 4: hydrogen; palladium 10% on activated carbon / ethyl acetate / 16 h / 20 °C / 5171.62 Torr / Autoclave
Multi-step reaction with 4 steps 1: triethylamine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 72 h / 0 - 20 °C 2: hydrogen; palladium on activated charcoal / tetrahydrofuran / 16 h / 30 °C 3: potassium carbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 18 h / 100 °C 4: hydrogen; palladium 10% on activated carbon / ethyl acetate / 16 h / 20 °C / 5171.62 Torr / Autoclave

Reference： [1]Current Patent Assignee: PURETECH HEALTH PLC - WO2020/28787, 2020, A1 Current Patent Assignee: PURETECH HEALTH PLC; MONASH UNIVERSITY - WO2020/176868, 2020, A1
[2]Current Patent Assignee: PURETECH HEALTH PLC - WO2020/176859, 2020, A1
[3]Current Patent Assignee: MONASH UNIVERSITY; PURETECH HEALTH PLC - WO2020/176856, 2020, A1
[4]Current Patent Assignee: MONASH UNIVERSITY; PURETECH HEALTH PLC - WO2021/159021, 2021, A1
  • 44
  • [ 67852-88-4 ]
  • C45H83ClO7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; triethylamine / dichloromethane / 72 h / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / tetrahydrofuran / 16 h / 30 °C 3: thionyl chloride; N,N-dimethyl-formamide / 1.25 h / Reflux
Multi-step reaction with 3 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; triethylamine / dichloromethane / 72 h / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / tetrahydrofuran / 16 h / 30 °C 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 1.25 h / Reflux
Multi-step reaction with 3 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; triethylamine / dichloromethane / 72 h / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / tetrahydrofuran / 16 h / 30 °C 3: N,N-dimethyl-formamide; thionyl chloride / 1.25 h / Reflux
Reference： [1]Current Patent Assignee: PURETECH HEALTH PLC - WO2020/28787, 2020, A1 Current Patent Assignee: PURETECH HEALTH PLC; MONASH UNIVERSITY - WO2020/176868, 2020, A1
[2]Current Patent Assignee: PURETECH HEALTH PLC - WO2020/176859, 2020, A1
[3]Current Patent Assignee: MONASH UNIVERSITY; PURETECH HEALTH PLC - WO2020/176856, 2020, A1
  • 45
  • [ 1159408-65-7 ]
  • [ 67852-88-4 ]
  • [ 2304374-11-4 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In di-isopropyl ether; N,N-dimethyl-formamide
Reference： [1]Bhingardeve, Pramod; Madhanagopal, Bharath Raj; Naick, Hemanth; Jain, Prashant; Manoharan, Muthiah; Ganesh, Krishna [Journal of Organic Chemistry, 2020, vol. 85, # 14, p. 8812 - 8824]
  • 46
  • [ 67852-88-4 ]
  • [ 518-28-5 ]
  • [ 1043908-30-0 ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: decanedioic acid monobenzyl ester; podofilox With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 4h; Stage #2: With palladium 10% on activated carbon; hydrogen In dichloromethane at 20℃; for 3h; 2.2. Synthesis of PPT-C10-Hinoki Monobenzyl sebacate (Bn-C10-OH) were synthesized according to the literature [16]. Toa solution of monobenzyl sebacate (340.6 mg, 1.165 mmol) in CH2Cl2 (12 mL, 0.1 M)was added PPT (484.6 mg, 1.169 mmol), EDCHCl (283.3 mg, 1.478 mmol), and DMAP(28.9 mg, 0.236 mmol) at room temperature. After stirring for 4 h, the reaction mixturewas concentrated under reduced pressure to give crude Bn-C10-PPT. The crude Bn-C10-PPT was dissolved in CH2Cl2 (10 mL), and then 10% Pd/C (66.3 mg) was added atroom temperature. After stirring for 3 h under hydrogen atmosphere, the reaction mixturewas filtered and concentrated under reduced pressure to give PPT-C10-OH(547.9 mg, 0.915 mmol, 78%, two steps). To a solution of PPT-C10-OH (266.9 mg,0.446 mmol) in CH2Cl2 (6 mL, 0.075 M) was added hinokitiol (79.4 mg, 0.484 mmol),EDCHCl (180.1 mg, 0.939 mmol), and DMAP (9.6 mg, 0.0786 mmol). After stirring for 4 h at room temperature, the reaction mixture was concentrated under reduced pressure.
Reference： [1]Kasai, Hitoshi; Koseki, Yoshitaka; Shimizu, Kazue; Tanita, Keita; Umezawa, Hirohito [Molecular Crystals and Liquid Crystals, 2020, vol. 706, # 1, p. 79 - 85]
  • 47
  • [ 67852-88-4 ]
  • [ 518-28-5 ]
  • C39H44O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; 2 Method for Producing Compound B of the Present Invention 10- (Benzyloxy) -10-oxodecanoic acid (64 mg, 0.219 mmol), podophylrotoxin (105 mg, 0.254 mmol), 1-ethyl- in a eggplant flask equipped with a stirrer bar. 3- (3-Dimethylaminopropyl) carbodiimide hydrochloride (94 mg, 0.492 mmol) and 4-dimethylaminopyridine (9 mg, 0.0696 mmol) were added and dissolved in 4.4 mL of dichloromethane. After stirring overnight at room temperature, the residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (chloroform) to obtain an ester (156 mg, 94%) as a transparent liquid. The obtained ester (144 mg, 0.209 mmol) and palladium carbon (14 mg) were placed in an eggplant flask equipped with a stirrer bar, and 2.1 mL of dichloromethane was added. After stirring at room temperature for 3 hours under a hydrogen atmosphere, carboxylic acid (104 mg, 83%) was obtained as a transparent liquid by filtration through Celite and distillation of the solvent under reduced pressure. Carboxylic acid (30 mg, 0.501 mmol), SN-38 (25 mg, 0.0627 mmol), 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (24 mg) obtained in a eggplant flask equipped with a stirrer bar. , 0.126 mmol), 4-dimethylaminopyridine (2.2 mg, 0.0180 mmol) was added and dissolved in 1 mL of dichloromethane. After stirring overnight at room temperature, the mixture was diluted with chloroform and washed with saturated aqueous ammonium chloride solution and saturated aqueous sodium chloride solution. The organic layer is dried over anhydrous magnesium sulfate, filtered, and the residue obtained by distilling off the solvent under reduced pressure is purified by silica gel column chromatography (chloroform → chloroform / methanol = 100: 1) to purify compound B (39 mg, 80%). Was obtained as a pale yellow solid.
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 4h; 2.2. Synthesis of PPT-C10-Hinoki Monobenzyl sebacate (Bn-C10-OH) were synthesized according to the literature [16]. Toa solution of monobenzyl sebacate (340.6 mg, 1.165 mmol) in CH2Cl2 (12 mL, 0.1 M)was added PPT (484.6 mg, 1.169 mmol), EDCHCl (283.3 mg, 1.478 mmol), and DMAP(28.9 mg, 0.236 mmol) at room temperature. After stirring for 4 h, the reaction mixturewas concentrated under reduced pressure to give crude Bn-C10-PPT. The crude Bn-C10-PPT was dissolved in CH2Cl2 (10 mL), and then 10% Pd/C (66.3 mg) was added atroom temperature. After stirring for 3 h under hydrogen atmosphere, the reaction mixturewas filtered and concentrated under reduced pressure to give PPT-C10-OH(547.9 mg, 0.915 mmol, 78%, two steps). To a solution of PPT-C10-OH (266.9 mg,0.446 mmol) in CH2Cl2 (6 mL, 0.075 M) was added hinokitiol (79.4 mg, 0.484 mmol),EDCHCl (180.1 mg, 0.939 mmol), and DMAP (9.6 mg, 0.0786 mmol). After stirring for 4 h at room temperature, the reaction mixture was concentrated under reduced pressure.
Reference： [1]Current Patent Assignee: TOHOKU UNIVERSITY - JP2021/147340, 2021, A Location in patent: Paragraph 0056
[2]Kasai, Hitoshi; Koseki, Yoshitaka; Shimizu, Kazue; Tanita, Keita; Umezawa, Hirohito [Molecular Crystals and Liquid Crystals, 2020, vol. 706, # 1, p. 79 - 85]
  • 48
  • [ 67852-88-4 ]
  • [ 191732-72-6 ]
  • benzyl 10-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)amino)-10-oxoheptanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 10-(benzyloxy)-10-oxodecanoic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 0.5h; Cooling with ice; Stage #2: Lenalidomide In N,N-dimethyl-formamide at 20℃; for 12h; General procedures for the preparation of compounds 6a-6e. General procedure: To a solution of 4a-4d (1.0 eq)in anhydrous DMF, HATU (2.0 eq) and DIEA (3.0 eq) were added. After stirring in an icebath for 0.5 h, 5a or 5b (1.0 eq) was added. The mixture was stirred at room temperatureovernight. After the reaction completed, the residue was diluted with H2O and extractedwith EtOAc. The combined organic layers were then washed with HCl (0.1 M), saturatedbrine, dried over anhydrous Na2SO4, and concentrated in vacuo to afford the crude product,which was purified by column chromatography with DCM/ MeOH (30:1-20:1) to produce6a-6e.
Reference： [1]Li, Jia; Lu, Wei; Lu, Yingxin; Shao, Yingying; Su, Mingbo; Sun, Danwen; Xiao, Donghuai; Zhou, Yubo; Zhu, Shulei [Molecules, 2021, vol. 26, # 23]
  • 49
  • tert-butyl (2-(4-aminobenzamido)phenyl)carbamate [ No CAS ]
  • [ 67852-88-4 ]
  • benzyl 10-((4-((2-((tert-butoxycarbonyl)amino)phenyl)carbamoyl)phenyl)amino)-10-oxodecanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃;
Reference： [1]Baker, India M.; Bowman, Karen J.; Cowley, Shaun M.; Hodgkinson, James T.; Lin, Li-Ying; Pytel, Wiktoria A.; Schwabe, John W. R.; Smalley, Joshua P. [Journal of Medicinal Chemistry, 2022, vol. 65, # 7, p. 5642 - 5659]
  • 50
  • [ 67852-88-4 ]
  • tert-butyl (2-(4-(10-(((S)-1-((2S,4R)-4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)amino)-10-oxodecanamido)benzamido)phenyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0 - 20 °C 2: hydrogen; palladium 10% on activated carbon / tetrahydrofuran 3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 16 h / 0 - 20 °C
Reference： [1]Baker, India M.; Bowman, Karen J.; Cowley, Shaun M.; Hodgkinson, James T.; Lin, Li-Ying; Pytel, Wiktoria A.; Schwabe, John W. R.; Smalley, Joshua P. [Journal of Medicinal Chemistry, 2022, vol. 65, # 7, p. 5642 - 5659]
  • 51
  • [ 67852-88-4 ]
  • N1-(4-((2-aminophenyl)carbamoyl)phenyl)-N10-((S)-1-((2S,4R)-4-hydroxy-2-((4-(4-methylthiazol5-yl)benzyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)decanediamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0 - 20 °C 2.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran 3.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 16 h / 0 - 20 °C 4.1: trifluoroacetic acid / dichloromethane / 20 °C 4.2: MP-carbonate resin / 20 °C
Reference： [1]Baker, India M.; Bowman, Karen J.; Cowley, Shaun M.; Hodgkinson, James T.; Lin, Li-Ying; Pytel, Wiktoria A.; Schwabe, John W. R.; Smalley, Joshua P. [Journal of Medicinal Chemistry, 2022, vol. 65, # 7, p. 5642 - 5659]
  • 52
  • [ 67852-88-4 ]
  • 10-((4-((2-((tert-butoxycarbonyl)amino)phenyl)carbamoyl)phenyl)amino)-10-oxodecanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0 - 20 °C 2: hydrogen; palladium 10% on activated carbon / tetrahydrofuran
Reference： [1]Baker, India M.; Bowman, Karen J.; Cowley, Shaun M.; Hodgkinson, James T.; Lin, Li-Ying; Pytel, Wiktoria A.; Schwabe, John W. R.; Smalley, Joshua P. [Journal of Medicinal Chemistry, 2022, vol. 65, # 7, p. 5642 - 5659]
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