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[ CAS No. 103321-52-4 ] {[proInfo.proName]}

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Chemical Structure| 103321-52-4
Chemical Structure| 103321-52-4
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Product Details of [ 103321-52-4 ]

CAS No. :103321-52-4 MDL No. :
Formula : C20H18ClNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 355.82 Pubchem ID :-
Synonyms :

Safety of [ 103321-52-4 ]

Signal Word: Class:
Precautionary Statements: UN#:
Hazard Statements: Packing Group:

Application In Synthesis of [ 103321-52-4 ]

* 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 [ 103321-52-4 ]

[ 103321-52-4 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 71989-31-6 ]
  • [ 103321-52-4 ]
YieldReaction ConditionsOperation in experiment
78.6% With thionyl chloride; N,N-dimethyl-formamide In dichloromethane for 1h; Ambient temperature;
76% With thionyl chloride In dichloromethane for 1.5h; Heating;
With thionyl chloride In dichloromethane for 0.5h; Heating; Yield given;
With pyridine; thionyl chloride In dichloromethane Heating;
With thionyl chloride In dichloromethane
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h;
With thionyl chloride In dichloromethane at 20℃; for 24h;
With oxalyl dichloride In N,N-dimethyl-formamide at 0 - 20℃; for 2h;
With thionyl chloride In toluene for 2h; Heating;
With thionyl chloride
With thionyl chloride In dichloromethane for 1h; Heating;
With thionyl chloride In dichloromethane for 0.5h; Sonication;
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane for 2h; Reflux;
With thionyl chloride In dichloromethane at 20℃; for 0.5h; 4.2.3. Synthesis of compound 2 Compound 3 (1.687 g, 5 mmol) was dissolved in CH2Cl2 (20 mL) and mixed with dripping SOCl2 (1 mL, 3 equiv). The mixture was stirred at room temperature for 30 min and decompressed at 40 °C to remove HCl formed during the reaction, as well as the solvent and superfluous SOCl2, generating a yellow oil product. Into the yellow oil were added NH4SCN (0.570 g, 7.5 mmol), polyethylene glycol (PEG)-400 (0.053 mL, 0.15 mmol) and CH2Cl2 (25 mL) at room temperature within 1 h to give isothiocyanate. A certain amount of resin 4 was then added to the mixture with isothiocyanate and stirred at room temperature. After being stirred for 24 h, water was added to dissolve the salt formed during the reaction, and ethanol was used to precipitate the product. Compound 2, either a yellow or light yellow solid, was obtained after filtering, and then washing with water, CH2Cl2 and acetone, and drying in a vacuum.
With 2,4,6-trimethyl-pyridine; bis(trichloromethyl) carbonate In tetrahydrofuran
With thionyl chloride for 5h; Reflux;
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3h;
With thionyl chloride In dichloromethane at 20℃; Sonication; Inert atmosphere;
With thionyl chloride In dichloromethane
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;
With thionyl chloride In dichloromethane at 37℃; for 1.75h; Synthesis of functionalized monomer 3 Fmoc-L-Pro (1.49g, 4.42mmol) was dissolved with CH2Cl2 (3mL) in a flask. To the resultant solution was slowly added 1mL of SOCl2 at 37°C with 15min of stirring. The mixture was stirred at 37°C for 1.5h to afford acyl chloride 2. Next, p-aminostyrene was dissolved in pyridine and added to acyl chloride 2 in 30min while the temperature was kept under 25°C for 6h. The resultant N-Fmoc was deprotected prior to polymerization with diethylamine with stirring overnight to give the functionalized monomer 3
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h; Inert atmosphere;
With thionyl chloride In dichloromethane at 20℃; Inert atmosphere; Sonication;
With 2,4,6-trimethyl-pyridine; bis(trichloromethyl) carbonate In tetrahydrofuran for 0.166667h; Inert atmosphere;
With thionyl chloride In dichloromethane for 3h; Reflux; 10 Synthesis of Fmoc-L-Proline Acid Chloride Fmoc-L-proline (250 mg, 0.74 mmol) was dissolved in CH2Cl2 (4 mL). Thionyl chloride (800 μL, 10.36 mmol) was added and the solution was stirred at reflux for 3 h with monitoring by quenching with methanol as a diluent and following the formation of the methanol adduct by TLC (CH2Cl2:MeOH; 9:1). Subsequently the reaction was dried in vacuo to give 250 mg of crude, which was then used in the subsequent reaction without any further purification.
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h;
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 2h; 9.1 Functionalization of Aza-peptide with native amino acid: [00303] 1. Preparation of the Fmoc-Pro(Cl): To a solution of Fmoc-Proline (1.0 g, 3.0 mmol) in DCM (lOmL) was added 0.1 mL of DMF. At 0°C, the reaction mixture was treated with thionyl chloride (2.0 mL). The reaction mixture was brought gradually to room temperature and left stirring for an additional 2h. The volatiles was removed under vacuum, and the residue was triturated with a solution of ether: hexane (1 : 1, v/v) (10 mL). The residue was dried under high vacuum for 30 min and used in the next step without further treatment.
With thionyl chloride In dichloromethane Sonication; 2.1. Brief Procedure for the Preparation of AminoacylChloride General procedure: In a 50 mL round bottomed flask, N-Fmoc-protectedamino acid (1mmol), dichloromethane (CH2Cl2) 6 mL andfreshly distilled thionyl chloride (1.2 mmol) was added andthe mixture was sonicated till the reaction completion, thereaction was monitored by TLC. After reaction, the excessof thionyl chloride and DCM were removed under vacuum,followed by addition of hexane separates solid product, itwas filtered and dried under vacuum taken directly for thereaction for the reaction [49].

Reference: [1]Carpino, Louis A.; Cohen, Beri J.; Stephens, Kenton E.; Sadat-Aalaee, S. Yahya; Tien, Jien-Heh; Langridge, Denton C. [Journal of Organic Chemistry, 1986, vol. 51, # 19, p. 3732 - 3734]
[2]Cianci, Julia; Baell, Jonathan B.; Harvey, Andrew J. [Tetrahedron Letters, 2007, vol. 48, # 34, p. 5973 - 5975]
[3]Beyermann, Michael; Bienert, Michael; Niedrich, Hartmut; Carpino, Louis A.; Sadat-Aalaee, Dean [Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 721 - 728]
[4]Jacobsen, Mogens Havsteen; Buchardt, Ole; Engdahl, Tom; Holm, Arne [Tetrahedron Letters, 1991, vol. 32, # 43, p. 6199 - 6202]
[5]Yen, Ya-Hew; Chu, Yen-Ho [Tetrahedron Letters, 2004, vol. 45, # 44, p. 8137 - 8140]
[6]Evindar, Ghotas; Batey, Robert A. [Journal of Organic Chemistry, 2006, vol. 71, # 5, p. 1802 - 1808]
[7]Babu, Vommina V. Suresh; Ananda, Kuppanna; Vasanthakumar, Ganga-Ramu [Journal of the Chemical Society. Perkin transactions I, 2000, # 24, p. 4328 - 4331]
[8]Brady, Stephen F.; Pawluczyk, Joseph M.; Lumma, Patricia K.; Feng, Dong-Mei; Wai, Jenny M.; Jones, Raymond; DeFeo-Jones, Deborah; Wong, Bradley K.; Miller-Stein, Cynthia; Lin, Jiunn H.; Oliff, Allen; Freidinger, Roger M.; Garsky, Victor M. [Journal of Medicinal Chemistry, 2002, vol. 45, # 21, p. 4706 - 4715]
[9]Caputo, Christine A.; Carneiro, Florentino D S.; Jennings, Michael C.; Jones, Nathan D. [Canadian Journal of Chemistry, 2007, vol. 85, # 2, p. 85 - 95]
[10]Jain, Hiteshkumar D.; Zhang, Chunchun; Zhou, Shuo; Zhou, Hao; Ma, Jun; Liu, Xiaoxiang; Liao, Xuebin; Deveau, Amy M.; Dieckhaus, Christine M.; Johnson, Michael A.; Smith, Kirsten S.; Macdonald, Timothy L.; Kakeya, Hideaki; Osada, Hiroyuki; Cook, James M. [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 8, p. 4626 - 4651]
[11]Guillena, Gabriela; Hita, Maria Del Carmen; Najera, Carmen; Viozquez, Santiago F. [Journal of Organic Chemistry, 2008, vol. 73, # 15, p. 5933 - 5943]
[12]Location in patent: experimental part Sureshbabu, Vommina V.; Chennakrishnareddy, Gundala [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 7, p. 981 - 988]
[13]Location in patent: scheme or table Lee, Jaekwang; Bae, Suyeal; Lee, Seo-Hee; Choi, Hojin; Kim, Young Hoon; Kim, Soo Jin; Park, Gyu Tae; Moon, Seung Kee; Kim, Dal-Hyun; Lee, Sungsook; Ahn, Soon Kil; Choi, Nam Song; Lee, Kyung Joo [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 21, p. 6327 - 6330]
[14]Location in patent: experimental part Li, Jia; Yang, Gengxu; Qin, Yanyan; Yang, Xinran; Cui, Yuanchen [Tetrahedron Asymmetry, 2011, vol. 22, # 6, p. 613 - 618]
[15]Location in patent: experimental part Sleebs, Marianne M.; Scanlon, Denis; Karas, John; Maharani, Rani; Hughes, Andrew B. [Journal of Organic Chemistry, 2011, vol. 76, # 16, p. 6686 - 6693]
[16]Location in patent: experimental part Liu, Jiawang; Wang, Yuji; Yang, Yifan; Jiang, Xueyun; Zhao, Ming; Wang, Wenjing; Wu, Guofeng; Wu, Jianhui; Zheng, Meiqing; Peng, Shiqi [ChemMedChem, 2011, vol. 6, # 12, p. 2312 - 2322]
[17]Location in patent: experimental part Sakamoto, Ken; Sato, Kohei; Shigenaga, Akira; Tsuji, Kohei; Tsuda, Shugo; Hibino, Hajime; Nishiuchi, Yuji; Otaka, Akira [Journal of Organic Chemistry, 2012, vol. 77, # 16, p. 6948 - 6958]
[18]Chaume, Gregory; Simon, Julien; Caupene, Caroline; Lensen, Nathalie; Miclet, Emeric; Brigaud, Thierry [Journal of Organic Chemistry, 2013, vol. 78, # 20, p. 10144 - 10153]
[19]Qu, Chengke; Zhao, Wenshan; Zhang, Lei; Cui, Yuanchen [Chirality, 2014, vol. 26, # 4, p. 209 - 213]
[20]Yoshida, Masahito; Sekioka, Naoki; Izumikawa, Miho; Kozone, Ikuko; Takagi, Motoki; Shin-ya, Kazuo; Doi, Takayuki [Chemistry - A European Journal, 2015, vol. 21, # 7, p. 3031 - 3041]
[21]Feng, Yu; Holte, Dane; Zoller, Jochen; Umemiya, Shigenobu; Simke, Leah R.; Baran, Phil S. [Journal of the American Chemical Society, 2015, vol. 137, # 32, p. 10160 - 10163]
[22]Guo, Guozhang; Wu, Yufeng; Zhao, Xiaowei; Wang, Jing; Zhang, Lei; Cui, Yuanchen [Tetrahedron Asymmetry, 2016, vol. 27, # 16, p. 740 - 746]
[23]Stephens, Thomas C.; Lodi, Mahendar; Steer, Andrew M.; Lin, Yun; Gill, Matthew T.; Unsworth, William P. [Chemistry - A European Journal, 2017, vol. 23, # 54, p. 13314 - 13318] Stephens, Thomas C.; Lawer, Aggie; French, Thomas; Unsworth, William P. [Chemistry - A European Journal, 2018, vol. 24, # 52, p. 13947 - 13953]
[24]Chaume, Grégory; Simon, Julien; Lensen, Nathalie; Pytkowicz, Julien; Brigaud, Thierry; Miclet, Emeric [Journal of Organic Chemistry, 2017, vol. 82, # 24, p. 13602 - 13608]
[25]Trân, Kien; Murza, Alexandre; Sainsily, Xavier; Coquerel, David; Côté, Jérôme; Belleville, Karine; Haroune, Lounès; Longpré, Jean-Michel; Dumaine, Robert; Salvail, Dany; Lesur, Olivier; Auger-Messier, Mannix; Sarret, Philippe; Marsault, Éric [Journal of Medicinal Chemistry, 2018, vol. 61, # 6, p. 2266 - 2277]
[26]Current Patent Assignee: CENTURION BIOPHARMA CORPORATION - US2019/2484, 2019, A1 Location in patent: Paragraph 0419; 0420
[27]Lawer, Aggie; Epton, Ryan G.; Stephens, Thomas C.; Palate, Kleopas Y.; Lodi, Mahendar; Marotte, Emilie; Lamb, Katie J.; Sangha, Jade K.; Lynam, Jason M.; Unsworth, William P. [Chemistry - A European Journal, 2020, vol. 26, # 55, p. 12674 - 12683]
[28]Current Patent Assignee: NORTHWELL HEALTH INC - WO2020/227592, 2020, A1 Location in patent: Paragraph 00303
[29]Kantharaju, Kamanna; Khatavi, Santosh Y. [Protein and Peptide Letters, 2021, vol. 28, # 6, p. 699 - 707]
  • 3
  • [ 112253-70-0 ]
  • [ 103321-52-4 ]
  • (9H-fluoren-9-yl)methyl 2-(5-bromo-2-carbamoylphenylcarbamoyl)pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; at 20℃; Example 5.25c. Synthesis of (9H-fluoren-9-yl)methyl 2-(5-bromo-2- carbamoylphenylcarbamovDpyrrolidine- 1 -carboxylateA solution of (9H-fluoren-9-yl)methyl 2-(chlorocarbonyl)pyrrolidine- l-carboxylate (600 mg, 1.8 mmol), <strong>[112253-70-0]2-amino-4-bromobenzamide</strong> (400 mg, 1.8 mmol), and Et3N (2 mL) in THF was stirred at room temperature . The reaction was monitored by TLC. After diluting with H20 (50 mL), the mixture was extracted with ethyl acetate (3 x 100 mL). The organic layers were dried over Na2S04 and concentrated to give yellow residue, which was purified by column chromatography. MS (ESI): 534, 536(MH+)
  • 4
  • C96H121N16O19PolS2 [ No CAS ]
  • [ 103321-52-4 ]
  • [ 53100-44-0 ]
  • Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
  • C70H105N21O16 [ No CAS ]
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