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[ CAS No. 53906-36-8 ]

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Chemical Structure| 53906-36-8
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CAS No. :53906-36-8 MDL No. :MFCD30532025
Formula : C10H18N2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :[H][C@]12CS[C@@H](CCCCCO)[C@@]1([H])NC(=O)N2
M.W :230.33 g/mol Pubchem ID :-
Synonyms :

Safety of [ 53906-36-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 53906-36-8 ]

  • Downstream synthetic route of [ 53906-36-8 ]

[ 53906-36-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 53906-36-8 ]
  • [ 304439-23-4 ]
YieldReaction ConditionsOperation in experiment
74% With bromine; triphenylphosphine In dichloromethane for 4h; Inert atmosphere; 3 (3) Synthesis of Compound S3: (3aS,4S,6afl)-4-(5-Bromo-pentyl)-tetrahvdro- thieno[3,4-c/limidazol-2-one Triphenylphosphine (0.390 g, 1 .50 mmol) was dissolved in anhydrous DCM (1 -2 mL) under nitrogen and transferred with a syringe to a solution of bromine (77 μΙ, 1 .50 mmol) in anhydrous DCM (3 mL) at 0°C. This solution was stirred for 10 min. The resulting yellow slurry was transferred with a syringe to a suspension of alcohol S2 (0.230 g, 1 .00 mmol) in anhydrous DCM (2 ml_). After complete dissolution of all reactants the reaction was monitored by TLC. After 4 h a white precipitate formed and the reaction was quenched by the addition of Na2S203solution (10 ml_, 0.1 M, aq) resulting in a colour change from yellow to colourless. Water (10 mL) was added and the organic layer was separated from the aqueous layer. The aqueous layer was extracted with DCM (3χ20 mL), and the combined organics were washed with water (3 x 10 mL), dried with Na2S04and the solvent removed in vacuo. The crude product was purified using column chromatography (DCM:MeOH, 90:10) to yield the bromide S3 as a colourless solid (0.220 g, 74%). R, (DCM:MeOH, 90:10) = 0.4; mp 166 °C; IR 3200 (NH), 1702 (C=0);1H NMR δ (400 MHz, CD3OD) 4.47 (1 H, dd, J = 7.8, 5.0, NHCHCH), 4.30 (1 H, dd, J = 7.9, 4.5, NHCHCH2), 3.44 (2H, t, J = 6.7, CH2Br), 3.23- 3.18 (1 H, m, SCH), 2.91 (1 H, dd, J = 12.7, 5.0, CHBS), 2.72 (1 H, d, J = 12.7, CHAHBS), 1 .86 (2H, qn, J = 7.0, CH2), 1 .80-1 .55 (2H, m, CH2), 1 .54-1 .40 (4H, m, CH2) ;13C NMR δ (126 MHz, CD3OD) 164.8 (CO), 62.0 (CH), 60.2 (CH), 55.7 (CH), 39.6 (CH2), 32.9 (CH2), 32.4 (CH2), 28.3 (CH2), 28.1 (CH2), 27.8 (CH2); m/z (ESI+, MeOH) 317 ([81BrM+Na]+, 25%), 315 ([79BrM+Na]+, 27), 213 (100).
74% With bromine; triphenylphosphine In dichloromethane at 0 - 20℃; for 2.33333h; Inert atmosphere;
Multi-step reaction with 2 steps 1: 94 percent / pyridine 2: 89 percent / LiBr / butan-2-one / 2 h / Heating
Multi-step reaction with 2 steps 1: pyridine 2: lithium bromide / butanone

  • 2
  • [ 608-16-2 ]
  • [ 53906-36-8 ]
YieldReaction ConditionsOperation in experiment
100% With diisobutylaluminium hydride In dichloromethane at -78 - 20℃; for 2.33333h; Inert atmosphere; 2 (2) Synthesis of Compound S2: (3aS,4S,6aff)-4-(5-Hvdroxy-pentyl)-tetrahvdro- thieno[3,4-c/limidazol-2-one Anhydrous DCM (40 mL) was added to biotin methyl ester S1 (0.529 g, 2.05 mmol) under nitrogen resulting in a colourless suspension. The solution was cooled to -78°C and DIBAL (6.23 mL, 7.12 mmol, 1 .0 M in DCM) was added dropwise. After stirring at -78 °C for 20 min the solution was allowed to warm to room temperature and was stirred for 2 h. The mixture was again cooled to -78°C and the reaction was quenched by the addition of MeOH (4.5 mL), followed by MeOH:H20 (15 mL, 2:1 ). The solvent was removed in vacuo and the residue was purified by column chromatography (DCM:MeOH, 90:10) to give alcohol S2 as a colourless solid (0.570 g, quantitative). Rf(DCM:MeOH, 90:10) = 0.2; mp 161
100% With diisobutylaluminium hydride In dichloromethane at -78 - 20℃; for 2.33333h;
73% With diisobutylaluminium hydride In dichloromethane at -78 - 20℃; Inert atmosphere;
71% With diisobutylaluminium hydride In dichloromethane at 0 - 20℃; for 3h; 2 Procedure 2: (3a5,45,6aR)-4-(5-hydroxypentyl)tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)- one (E-3) To a stirring solution of compound E-2 (800 mg, 3.10 mmol) in CH2CI2(20 mL) at 0 °C was added diisobutylaluminum hydride (1.0 M in CH2CI2; 10.8 mL, 10.8 mmol) dropwise. The resulting reaction mixture was stirred at this temperature for 2 h. After warming to rt, stirring was continued for a further 1 h. Methanol/water (10 ml; 1:1) was added and the mixture was stirred vigorously for 10 min. After concentrating to dryness in vacuo, the residue was taken up in ethanol (10 mL) and then sonicated. The ethanolic mixture was filtered through Celite, and the filtrate was concentrated in vacuo to afford compound E-3 (503 mg, 71%) as a white solid.1H NMR (300 MHz, Methanol-d4) p δpm: 4.51 (ddd, J= 7.9, 5.0, 1.0 Hz, 1H), 4.32 (dd, J= 7.9, 4.4 Hz, 1H), 3.57 (t, J = 6.4 Hz, 2H), 3.23 (ddd, J = 8.9, 5.7, 4.4 Hz, 1H), 2.95 (dd, J = 12.8, 5.0 Hz, 1H), 2.72 (d, J = 12.7 Hz, 1H), 1.83 - 1.34 (m, 8H).
52% With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 6h; Inert atmosphere; Cooling with ice;
22% With lithium aluminium tetrahydride In tetrahydrofuran at 80℃; for 20h;
With lithium aluminium tetrahydride In tetrahydrofuran
With lithium aluminium tetrahydride In tetrahydrofuran
With lithium aluminium tetrahydride In tetrahydrofuran
2.91 g With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere;

Reference: [1]Current Patent Assignee: THE UNIVERSITY OF EDINBURGH - WO2013/144604, 2013, A1 Location in patent: Page/Page column 40
[2]Germeroth, Anne I.; Hanna, Jill R.; Karim, Rehana; Kundel, Franziska; Lowther, Jonathan; Neate, Peter G. N.; Blackburn, Elizabeth A.; Wear, Martin A.; Campopiano, Dominic J.; Hulme, Alison N. [Organic and Biomolecular Chemistry, 2013, vol. 11, # 44, p. 7700 - 7704]
[3]Location in patent: experimental part Iglesias-Sanchez, Jose Carlos; Maria, Dolores Santa; Claramunt, Rosa M.; Elguero, Jose [Molecules, 2010, vol. 15, # 3, p. 1213 - 1222]
[4]Current Patent Assignee: PHARMAXIS LTD - WO2021/155439, 2021, A1 Location in patent: Paragraph 00186
[5]Fontaine, Devon F. A.; Ivancic, Valerie A.; Reardon, Michael B.; Lazo, Noel D.; Jakobsche, Charles E. [Organic and Biomolecular Chemistry, 2017, vol. 15, # 38, p. 8023 - 8027]
[6]Current Patent Assignee: GHENT UNIVERSITY - WO2019/166475, 2019, A1 Location in patent: Page/Page column 35
[7]Umeda, Nobuhiro; Ueno, Tasuku; Pohlmeyer, Christopher; Nagano, Tetsuo; Inoue, Takanari [Journal of the American Chemical Society, 2011, vol. 133, # 1, p. 12 - 14]
[8]Location in patent: scheme or table Soares Da Costa, Tatiana P.; Tieu, William; Yap, Min Y.; Zvarec, Ondrej; Bell, Jan M.; Turnidge, John D.; Wallace, John C.; Booker, Grant W.; Wilce, Matthew C. J.; Abell, Andrew D.; Polyak, Steven W. [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 6, p. 509 - 514]
[9]Tieu, William; Polyak, Steven W.; Paparella, Ashleigh S.; Yap, Min Y.; Soares Da Costa, Tatiana P.; Ng, Belinda; Wang, Geqing; Lumb, Richard; Bell, Jan M.; Turnidge, John D.; Wilce, Matthew C. J.; Booker, Grant W.; Abell, Andrew D. [ACS Medicinal Chemistry Letters, 2015, vol. 6, # 2, p. 216 - 220]
[10]Siebertz, Kristina D.; Hackenberger, Christian P. R. [Chemical Communications, 2018, vol. 54, # 7, p. 763 - 766]
[11]Anderl, Felix; Balkenhohl, Moritz; Carreira, Erick M.; Fink, Moritz; Pfaff, Patrick [Journal of the American Chemical Society, 2021, vol. 143, # 36, p. 14495 - 14501]
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  • [ 1231709-98-0 ]
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  • [ 120550-35-8 ]
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YieldReaction ConditionsOperation in experiment
94% With sodium tetrahydroborate; In N,N-dimethyl-formamide; at 0℃; for 0.25h; D-Biotin (1.00 g, 4.09 mmol) was dissolved in 20 mL DMF at 70 C and allowed to cool to rt. TEA (0.83g, 1.14 mL, 8.19 mmol) was added, followed by pentafluorophenyl trifluoroacetate (1.60 g, 0.98 mL, 5.73 mmol). The reaction was allowed to stir for 1 h at 0 C and became pink. Solvent was reduced to 1 mL in vacuo and the crude material was triturated with cold diethyl ether. The pFp ester product was recovered as a white solid (1.54 g, 96%). Biotin-pFp ester (1.00 g, 2.44 mmol) was dissolved in 10 mL DMF and cooled to 0 C. A flask containing a suspension of NaBH4 (3.4 mmol) in dry DMF (5 mL) was also cooled to 0 C. The pFp-ester was transferred dropwise via a cannula over 15 min and the mixture was stirred at 0 C. The reaction was followed by TLC and upon completion the cold mixture was acidified with 1 N HC1 and reduced to 1 mL in vacuo. The residue was triturated with cold diethyl ether and the product alcohol was recovered as a white solid (0.528 g, 94%). The alcohol (0.528 g, 2.29 mmol) and TEA (0.39 ml, 1.2 eq) were dissolved in DMF (10 mL) and added dropwise to a stirred solution of 4-nitrophenyl chloroformate (4-NCF, 1.38 g, 6.87 mmol, 3.0 eq) in DMF (10 mL) over a period of 1 h at -10C. The reaction mixture was allowed to warm to rt, stirred overnight, and subsequently and reduced to 1 mL in vacuo. The residue was triturated with cold diethyl ether. The nitrophenol carbonate product was recovered as a white solid (0.96 g, 95%). Fmoc-L-Lys-OH (1.03 g, 2.83 mmol, 1.3 eq.) was suspended under argon in anhydrous DMF (10 ml) containing DiPEA (0.50 ml, 1.3 eq.). To this white suspension, a clear solution of the nitrophenol-carbonate (2.18 mmol, 1.0 eq.) in anhydrous DMF (10 mL) was added drop wise under argon at rt over a period of 2 h. The reaction mixture was stirred for additional 4 h at rt, before the solution as acidified to pH 2 with 1 N HC1. All volatiles were evaporated under reduced pressure and the residue was triturated with cold diethyl ether. The crude product was purified by column chromatography (DCM : MeOH 95 : 5 v/v) to give the Fmoc-protected ncAA as a white solid. The Fmoc- protected ncAA was dissolved in 20% piperidine in DMF (5 ml) and stirred for 1 h at r.t.. All volatiles were removed under reduced pressure and the residue was triturated with cold diethyl ether. Drying of the residue in vaccuum yield the pure ncAA as a white powder (0.622 g, 71 %). 1H-NMR (D6-DMSO, 400 MHz): delta = 1.30-1.45 (m, 6H), 1.50-1.65 (m, 4H), 1.85 (m, 2H), 2.65 (d, J = 12.2 Hz, 1H), 2.84 (dd, J= 5.0 Hz, J= 12.2 Hz, 1H), 2.95 (m, 2H), 3.13 (m, 1H), 3.42 (m, 1H), 3.66 (m, 1H), 3.85 (dd, J= 13.8 Hz, J = 1.0 Hz 1H), 3.93 (t, J= 7.5 Hz, 2H), 4.17 (dd, J= 8.2 Hz, J= 7.3 Hz, 1H), 4.35 (dd, J= 8.1 Hz, J= 7.2 Hz, 1H), 7.11 (t, J= 5.4 Hz, 1H), 8.50 (br, 3H), 8.53 (br, 1H), 8.68 (br, 1H).13C-NMR (D6-DMSO, 100 MHz): 13C-NMR (CDCI3, 100 MHz): delta = 171.44, 163.29, 156.82, 64.00, 61.61, 60.35, 59.79, 55.95, 52.28, 39.10, 30.05, 29.35, 29.02, 28.78, 28,73, 25.91, 22.05. HR-MS (C17H31N4O5S): calculated: 403.20097, found: 403.20159.
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