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Chemical Structure| 83948-53-2 Chemical Structure| 83948-53-2
Chemical Structure| 83948-53-2

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CAS No.: 83948-53-2

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3-(Boc-amino)propyl bromide is a bromide derivative of a Boc-protected amine, typically used in the synthesis of peptides and other bioactive molecules.

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Product Citations      Show More

Julianna M. Mouat ; Jonas K. Widness ; Daniel G. Enny ; Mahilet T. Meidenbauer ; Farwa Awan ; Todd D. Krauss , et al.

Abstract: Semiconductor quantum dots (QDs) offer many advantages as photocatalysts for synthetic photoredox catalysis, but no reports have explored the use of QDs with nickel catalysts for C–C bond formation. We show here that 5.7 nm CdS QDs are robust photocatalysts for photoredox-promoted cross-electrophile coupling (turnover number (TON) up to 40,000). These conditions can be utilized on a small scale (96-well plate) or adapted to flow. NMR studies show that triethanolamine (TEOA)-capped QDs are the active catalyst and that TEOA can displace native phosphonate and carboxylate ligands, demonstrating the importance of the QD surface chemistry.

Keywords: quantum dot ; nanoplatelet ; nickel ; cross-electrophile coupling ; C?C bond formation ; photochemistry

Purchased from AmBeed: ; ; ; ;

Zhou, Jujun ; Deng, Youchao ; Iyamu, Iredia D. ; Horton, John R. ; Yu, Dan ; Hajian, Taraneh , et al.

Abstract: S-Adenosyl-L-methionine (SAM) analogs are adaptable tools for studying and therapeutically inhibiting SAM-dependent methyltransferases (MTases). Some MTases play significant roles in host-pathogen interactions, one of which is Clostridioides difficile-specific DNA adenine MTase (CamA). CamA is needed for efficient sporulation and alters persistence in the colon. To discover potent and selective CamA inhibitors, we explored modifications of the solvent-exposed edge of the SAM adenosine moiety. Starting from the two parental compounds (6e and 7), we designed an adenosine analog (11a) carrying a 3-phenylpropyl moiety at the adenine N6-amino group, and a 3-(cyclohexylmethyl guanidine)-Et moiety at the sulfur atom off the ribose ring. Compound 11a (IC50 = 0.15 μM) is 10x and 5x more potent against CamA than 6e and 7, resp. The structure of the CamA-DNA-inhibitor complex revealed that 11a adopts a U-shaped conformation, with the two branches folded toward each other, and the aliphatic and aromatic rings at the two ends interacting with one another. 11a occupies the entire hydrophobic surface (apparently unique to CamA) next to the adenosine binding site. Our work presents a hybrid knowledge-based and fragment-based approach to generating CamA inhibitors that would be chem. agents to examine the mechanism(s) of action and therapeutic potentials of CamA in C. difficile infection.

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Product Details of 3-(Boc-amino)propyl bromide

CAS No. :83948-53-2
Formula : C8H16BrNO2
M.W : 238.12
SMILES Code : O=C(NCCCBr)OC(C)(C)C
MDL No. :MFCD02683429
InChI Key :IOKGWQZQCNXXLD-UHFFFAOYSA-N
Pubchem ID :4460490

Safety of 3-(Boc-amino)propyl bromide

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501

Application In Synthesis of 3-(Boc-amino)propyl bromide

* 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 [ 83948-53-2 ]

[ 83948-53-2 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 34074-22-1 ]
  • [ 83948-53-2 ]
  • [ 913172-12-0 ]
  • 2
  • [ 83948-53-2 ]
  • [ 173963-91-2 ]
  • 3
  • [ 68631-52-7 ]
  • [ 83948-53-2 ]
  • [ 945489-94-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 15h; The diethyl ester of chelidamic acid (Scrimin, P.; Tecilla, P.; Tonellato, U.; Vendrame, T. J. Org. Chem. 1989, 54, 5988) (150mg) was dissolved in dry dimethylformamide (2 mL). 3-(tert-Butoxy-amino)-propyl bromide (164 mg) and potassium carbonate (130 mg) were added. The resulting mixture was stirred for 15h at 70C. The reaction was quenched with a saturated ammonium chloride aqueous solution and then washed into separatory funnel using ethyl acetate. The layers were separated, and the aqueous layer was extracted 3 times with ethyl acetate. The combined organic solutions were dried over magnesium sulfate, and concentrated in vacuo to a residue. The residue was purified by silica gel chromatography (Merck SuperVarioFlash 30g column, Si60 15-40mum), using gradient elution with a mixture of heptane (A) and ethyl acetate (B) (gradient : 60% A : 40% B up to 50% A : 50% B) to give 4-(3-tert-butoxycarbonylamino-propoxy)-pyridine-2,6-dicarboxylic acid diethyl ester (150 mg) : Cl (Method D) :m/z=397 MH+ 1H N.M.R. (400 MHz, DMSO-d6, delta in ppm) : 1,34 (t, J = 7,0 Hz, 6H) ; 1,36 (s, 9H) ; 1,86 (m, 2H) ; 3,10 (q, J = 6,5 Hz, 2H) ; 4,21 (t, J = 6,5 Hz, 2H) ; 4,37 (q, J = 7,0 Hz, 4H) ; 6,89 (m broad, 1 H) ; 7,71 (s, 2H)
  • 4
  • [ 24424-99-5 ]
  • [ 656-35-9 ]
  • [ 821-48-7 ]
  • [ 83948-53-2 ]
  • 1-(3-aminopropyl)-4-(2,4-difluorophenyl)-piperidine-4-carbonitrile dihydrochloride [ No CAS ]
  • 5
  • [ 6374-91-0 ]
  • [ 83948-53-2 ]
  • [ 1354973-83-3 ]
YieldReaction ConditionsOperation in experiment
62% General procedure: 5,7-dibromoisatin 2 (1 g, 3.28 mmol) was taken up in anhydrous DMF (30 mL) and cooled on ice with stirring. Solid K2CO3 (544 mg, 3.94 mmol) was added in one portion, and the dark colored suspension was brought to room temperature and stirred for a further 1 h. 1-Bromo-3-chloropropane (620 mg, 3.94 mmol, 0.387 mL) was added slowly with constant stirring and the reaction mixture was stirred at 80 C for 4-8 h, until the 5,7-dibromoisatin starting material had been consumed (TLC). The reaction mixture was poured into HCl (0.5 M, 50 mL) and extracted with ethyl acetate (3 × 50 mL). The ethyl acetate layer was washed with brine and dried over MgSO4. The solvent was removed, and the crude product was purified by silica gel column chromatography (CH2Cl2 as eluent) to give pure 3 (0.93 g, 74%) as orange red crystals.
  • 6
  • [ 1080-12-2 ]
  • [ 83948-53-2 ]
  • tert-butyl (3-(2-methoxy-4-(3-oxobut-1-en-1-yl)phenoxy)propyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
9% With potassium carbonate; In acetone; at 65℃; for 3h;Microwave irradiation; A mixture of 4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one (2) (101.6 mg, 0.311 mmol), 3-(boc-amino) propyl bromide (137 mg, 0.575 mmol), K2CO3 (105.2 mg, 0.76 mmol), and acetone (30 mL), was placed in an opened microwave reactor. The mixture under stirring was irradiated at 200 W for 3 h, at a final temperature of 65 C. The solid was removed by filtration with a sintered glass Buchner funnel under reduced pressure. The yellow solution was purified by semi-flash chromatography (SiO2; n-hexane:diethyl ether: several proportions). The fractions that eluted with n-hexane: diethyl ether 7.5:2.5 were gathered and after solvent evaporation a recrystallization from diethyl ether: petroleum ether(4:1) was performed providing a yellow solid of tert-butyl (3-(2-methoxy-4-(3-oxobut-1-en-1-yl)phenoxy)propyl)carbamate(8, 16.6 mg, 9%). mp 108-110 C (diethyl ether: petroleum ether). Purity 96%. IR(KBr)mmaxcm-1 3377, 1686, 1669, 1644, 1621, 1595, 1518, 1273,1260, 1225, 1167, 1138, 1033, 975. 1H NMR (CDCl3, 300 MHz) d: 7.46 (1H,d, J= 16.2 Hz, H-3), 7.11 (1H,d, J= 8.2 Hz, H-60), 7.07(1H,s, H-20), 6.86 (1H, d, J= 8.2 Hz, H-50), 6.61 (1H, d, J= 16.2 Hz,H-2), 5.50 (1H,brs, H-100) 4.14 (2H, t, J= 5 Hz, H-70), 3.92 (3H, s, 30-OCH3), 3.38 (2H, d, J= 5 Hz, H-90), 2.38 (3H, s, H-100), 2.04 (2H,t, J= 5 Hz, H-80), 1.46 (9H,s, H-110); 13C NMR (75.47 MHz, CDCl3) d: 198.4 (C-1), 156.1 (C-100), 150.5 (C-40), 149.5 (C-30), 143.5(C-3), 127.6 (C-10), 125.3 (C-2), 122.9 (C-60), 112.2 (C-50), 109.7(C-20), 79.0 (C-110), 68.2 (C-70), 55.8 (30-OCH3), 38.9 (C-90), 30.9(C-80), 28.5 (C-120), 27.4 (C-100). EI-MS (70e V) m/z (rel. intensity,%): 349 (M+, 96), 308 (32), 261 (38), 253 (52). HRMS- ESI (+) m/z: Anal. Calc. for C19H27NO5[MH]+ 350.19675, found 350.19620
  • 7
  • [ 1025718-84-6 ]
  • [ 83948-53-2 ]
  • tert-butyl 3-(3-bromo-5-(trifluoromethyl)phenoxy)propylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 120℃; for 6.0h; [00347] Synthesis of tert-butyl 3-(3-bromo-5-(trifluoromethyl)phenoxy)propylcarbamate (10): 3-Bromo-5-(trifluoromethyl)phenol (2 g, 8.4 mmol) was dissolved in 35 mL of DMF. tert-Butyl 3-bromopropylcarbamate (2.03 g, 8.4 mmol), K2CO3 (3.49 g, 25.2 mmol) and KI (2.7 g, 16.8 mmol) were added. The reaction was stirred at 120 C for 6 h. After cooling to room temperature, the mixture was poured into 35 mL of H20 and extracted with EtO Ac (50 mL X 3). The combined organic solvents were dried over anhydrous Na2S04, concentrated and purified by silica gel chromatography (40-80% EtO Ac/petroleum ether) to give 1.5 g of tert-butyl 3-(3-bromo-5-(trifluoromethyl)phenoxy)propylcarbamate (10). Yield: 45%. LCMS: m/z 344.1 [M-55]+; tR = 2.35 min.
  • 8
  • [ 1025718-84-6 ]
  • [ 83948-53-2 ]
  • tert-butyl 3-(4'-(4,4-difluoropiperidine-1-carbonyl)-5-(trifluoromethyl)biphenyl-3-yloxy)propylcarbamate [ No CAS ]
 

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