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Chemistry
Organic Building Blocks
Amines
5-((tert-Butoxycarbonyl)amino)pentyl methanesulfonate
Chemistry
Organic Building Blocks
Amines
Amides Sulfonates Aliphatic Chain Hydrocarbons

[ CAS No. 142342-55-0 ] {[proInfo.proName]}

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Chemical Structure| 142342-55-0
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CAS No. :142342-55-0 MDL No. :MFCD08448236
Formula : C11H23NO5S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 281.37 Pubchem ID :-
Synonyms :

Safety of [ 142342-55-0 ]

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Application In Synthesis of [ 142342-55-0 ]

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

  • Downstream synthetic route of [ 142342-55-0 ]

[ 142342-55-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 75178-90-4 ]
  • [ 124-63-0 ]
  • [ 142342-55-0 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine; In dichloromethane; at 20℃; terf-Butyl 5-hydroxypentylcarbamate (2g, 9.8 mmol) was dissolved in anhydrous dichloromethane (20 mL) and cooled to O0C. Triethylamine (2.46 ml_, 17.7 mmol) was added dropwise followed by slow addition of methanesulfonyl chloride (1.13 mL, 14.7 mmol). The mixture was stirred at room temperature overnight and quenched with saturated sodium bicarbonate solution. The reaction mixture was extracted with dichloromethane and the combined organic layers washed with water and brine. The organic extract was dried(MgSO4) filtered, and concentrated to afford 211 as a yellow solid in quantitative yield. LRMS(ESI): (calc) 281.1 ; (found), 304.1 (M+Na)+
97% With triethylamine; In dichloromethane; at -10℃; for 3h; To a stirred mixture of tert-butyl 5-hydroxypentylcarbamate (2)(9.8 g, 48.2 mmol) and triethyl amine (13.44 mL, 96.0 mmol) in DCM (85 mL) at-10 oC was added methanesulfonyl chloride (4.5 mL, 57.9 mmol) in adropwise fashion and the resulting solution was stirred at the same temperaturefor 3h. The reaction was quenched with the addition of water (5 mL). Theorganic phase was washed with water, brine, dried over MgSO4,filtered and evaporated under reduced pressure to afford the title compound asyellow oil (13.16g, 97%). The product was directly taken to next step withoutany further purification. 1H NMR(CDCl3) d 4.22 (t, 2H, J = 6.42 Hz), 3.09 (m, 2H), 1.82 (m, 4H), 1.56-1.40(m, 11H). 13C NMR (75 MHz, CDCl3) d 155.8, 79.3, 70.0,41.8, 37.9, 29.8, 28.3, 22.5. IR: 2981, 1707, 1516, 1354, 1171 cm-1. MS m/z (ESI) 304.26 (M +Na+).
86.9% With triethylamine; In dichloromethane; for 1.33333h;Cooling with ice; To a solution of 42 (10 g, 49.2 mmol) in DCM (100 mL) and Et3N (9.9 g, 98.5 mmol) was added methanesulfonyl chloride (6.7 g, 59.1 mmol) in portions over 20 minutes under an ice bath. The reaction was stirred for 1 hour. The mixture was extracted with DCM. The combined organic layers were washed with saturated NaCl, dried over a2S04, and filtered. The filtrate was concentrated to give 43 (12 g, yield: 86.9 %). XH NMR (300 MHz, CDC13) delta: 4.0 (m, 2H), 3.1-3.0 (m, 3H), 3.2-3.1 (m, 2H),1.6-1.5 (m, 4H), 1.4-1.3 (m, 11H).
81% With triethylamine; In diethyl ether; benzene; at 8 - 20℃; for 7h; MsCl (2.07 g, 18.1 mmol) in 7 mL ofdry C6H6 was added during 20 min under stirring to thecooled (8C) solution of 5NBocaminopentanol1(3.86 g, 19 mmol) and Et3N (2.53 g, 25 mmol) in40 mL of C6H6/Et2O (2 : 1). The mixture was stirredfor 1 h at 8C and 6 h at 20C. The precipitate was filtered, and filtrates were washed successively with 1 NaHCO3 (3 × 10 mL), H2O (10 mL), 10% citric acid(2 × 10 mL), H2O (5 mL), and 5 NaCl (15 mL) anddried over MgSO4/NaHCO3. The solvent was evaporated in vacuum, the residue was triturated with hexane, the precipitate was filtered and dried in air,recrystallized from an Et2Ohexane mixture. Compound (X) was obtained in a yield of 4.32 g (81%).
80% With triethylamine; In dichloromethane; at -10℃; for 5h; General procedure: To a stirred solution of tert-butyl 5-hydroxypentyl-carbamate(500 mg, 2.46 mmol) and TEA (498 mg, 4.92 mmol) in 5mL DCMat -10 C was added MsCl (338 mg, 2.95 mmol) dropwise and thesolution was stirred at the same temperature for 5 h. The reactionwas then quenched with water. The organic layer was washed withwater, brine, dried over MgSO4, filtered and evaporated underreduced pressure to give the desired product as yellow oil (552 mg,80%, Rf 0.5 (EtOAc)) The mesylatewas used in the next step withoutany further purification. Under N2 atmosphere 5-(tert-butoxycarbonylamino)pentyl methanesulfonate (350 mg, 1.2 mmol) wasdissolved in 5mL THF followed by the addition of LiBr (313 mg,3.6 mmol) to the solution. The reaction mixture was stirred for 16 hunder reflux, then THF was removed under vacuum. The mixturewas diluted with 10 mL water and it was extracted with DCM(3 x 10 mL). The combined organic phase was washed with water(3 x 10 mL) and brine (3 x 10 mL), dried over MgSO4 and evaporatedin vacuo. The product was purified by column chromatographyon silica gel 60 (n-hexane-EtOAc 9:1) to give whitecrystalline product (230 mg, 72%).
With triethylamine; In dichloromethane; at 0 - 20℃; for 5.5h; General procedure: To a solution of N-Boc protected alcohol (60 mmol) and TEA (60 mmol) in dry DCM (100 mL) kept in an ice bath (0 C) was slowly added methane sulfonyl chloride (60 mmol)) and reaction mixture was stirred for 30 min at 0 C. The ice bath was removed and reaction mixture was further allowed to stir at room temperature for 5 h (Completion of the reaction was monitored by TLC). Then water (50 mL) was added with stirring, the resulting solution was transferred to a reparatory funnel, organic layer was separated and aqueous layer was extracted with DCM (2 × 75 mL). The combined organic layers were washed with brine (50 mL) dried over anhydrous sodium sulfate and concentrated on rotary evaporator. See individual experiments for more details.

Reference： [1]Patent: WO2006/102760,2006,A1 .Location in patent: Page/Page column 133
[2]Tetrahedron Letters,1992,vol. 33,p. 2833 - 2836
[3]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2808 - 2811
[4]Bioconjugate Chemistry,2018,vol. 29,p. 3571 - 3585
[5]Patent: WO2013/116682,2013,A1 .Location in patent: Paragraph 00224
[6]Journal of Medicinal Chemistry,2015,vol. 58,p. 5287 - 5307
[7]Russian Journal of Bioorganic Chemistry,2016,vol. 42,p. 415 - 422
[8]European Journal of Medicinal Chemistry,2019,vol. 178,p. 571 - 588
[9]MedChemComm,2019,vol. 10,p. 1037 - 1041
[10]Synthesis,1990,p. 366 - 368
[11]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4828 - 4832
[12]Tetrahedron Letters,2004,vol. 45,p. 7081 - 7085
[13]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4892 - 4895
[14]Journal of Medicinal Chemistry,2014,vol. 57,p. 4924 - 4939
[15]European Journal of Medicinal Chemistry,2016,vol. 119,p. 300 - 318
[16]Patent: CN109824547,2019,A .Location in patent: Paragraph 0014
[17]Journal of Medicinal Chemistry,2019,vol. 62,p. 4755 - 4771
  • 2
  • [ 142342-55-0 ]
  • [ 74-89-5 ]
  • [ 1311458-36-2 ]
YieldReaction ConditionsOperation in experiment
56.5% In 1,4-dioxane; water at 60℃; for 1h; 8 To a solution of 43 (12 g, 42 mmol) in 1,4-dioxane (100 mL) was added CH3NH2 aqueous slowly (30 %, 100 ml) at 60°C. The mixture was stirred at 60 °C for lh. The reaction was concentrated and purified by a silica gel column (eluting with 3%Et3N/THF) to give 44 (5.2g, yield 56.5 %). 'H NMR (300 MHz, CDC13) δ: 3.2-3.1 (s, 2H) 2.9-2.9 (m, 3H), 2.6- 2.5(m, 2H), 1.6-1.5 (s, 2H), 1.4-1.3(s, 1 1H).
Reference： [1]Current Patent Assignee: ENSEMBLE THERAPEUTICS CORPORATION - WO2013/116682, 2013, A1 Location in patent: Paragraph 00225
  • 3
  • [ 10576-12-2 ]
  • [ 142342-55-0 ]
  • 1-(ethoxyethylideneaminooxy)-5-(N-tert-butyloxycarbonyl)aminopentane [ No CAS ]
YieldReaction ConditionsOperation in experiment
In isopropyl alcohol; at 20℃; for 42h; Compound (X) (4 g, 14.3 mmol) was added insmall portions at 20C under stirring to 1 M solutionof Na salt of oxyimino ether (V) (14.7 mL) in dryiPrOH. The reaction mixture was stirred for 42 h at20C. The precipitate was filtered; filtrate was evaporated in vacuum to dryness; the residue was dissolvedin CHCl3 (40 mL) and washed successively with H2O(5 mL), 1 M NaHCO3 (2 × 5 mL), H2O (5 mL). The chloroform solution was evaporated in vacuum to dryness to obtain crude 1(ethoxyethylideneaminooxy)5Ntertbutyloxycarbonyl]aminopentane (XII). Rf,0.60 (A). HCl conc. (25 mL) was added to the solutionof (XII) in EtOH (30 mL). After 3 h at 20, the reaction mixture was evaporated to dryness; the residuewas coevaporated with H2O (3 × 20 mL). Compound(XIII) was isolated by ionexchanged chromatographyon Dowex 508 (100-200 mesh; H+ form; Vcol,20 mL) using successive elution with H2O, 0.5 M HCl,and 1 M HCl. Fractions containing compound (XIII)were evaporated in vacuum to dryness; the residue wascoevaporated with H2O (4 × 10 mL), dried in vacuumover P2O5/KOH, and recrystallized from dry EtOH.Compound (XIII) was obtained in a yield of 1.0 g(43% relative to (X).
Reference： [1]Russian Journal of Bioorganic Chemistry,2016,vol. 42,p. 415 - 422
  • 4
  • [ 142342-55-0 ]
  • [ 83948-54-3 ]
YieldReaction ConditionsOperation in experiment
72% With lithium bromide; In tetrahydrofuran; for 16h;Inert atmosphere; Reflux; To a stirred solution of tert-butyl 5-hydroxypentyl-carbamate(500 mg, 2.46 mmol) and TEA (498 mg, 4.92 mmol) in 5mL DCMat -10 C was added MsCl (338 mg, 2.95 mmol) dropwise and thesolution was stirred at the same temperature for 5 h. The reactionwas then quenched with water. The organic layer was washed withwater, brine, dried over MgSO4, filtered and evaporated underreduced pressure to give the desired product as yellow oil (552 mg,80%, Rf 0.5 (EtOAc)) The mesylatewas used in the next step withoutany further purification. Under N2 atmosphere 5-(tert-butoxycarbonylamino)pentyl methanesulfonate (350 mg, 1.2 mmol) wasdissolved in 5mL THF followed by the addition of LiBr (313 mg,3.6 mmol) to the solution. The reaction mixture was stirred for 16 hunder reflux, then THF was removed under vacuum. The mixturewas diluted with 10 mL water and it was extracted with DCM(3 x 10 mL). The combined organic phase was washed with water(3 x 10 mL) and brine (3 x 10 mL), dried over MgSO4 and evaporatedin vacuo. The product was purified by column chromatographyon silica gel 60 (n-hexane-EtOAc 9:1) to give whitecrystalline product (230 mg, 72%). Rf 0.6 (n-hexane-EtOAc 4:1); 1HNMR (300 MHz, CDCl3) delta 4.59 (brs, 1H, NH), 3.37 (t, 2H, J = 8.4 Hz, 5-H), 3.09 (q, 2H, J = 7.8 Hz, 1-H), 1.84 (quin, 2H, J = 7.3 Hz, 4-H),1.49-1.36 (m, 4H, 2-H, 3-H), 1.40 (s, 9H, CH3); 13C NMR (300 MHz,CDCl3) delta 155.9 (CONH), 79.0 (C(CH3)3), 40.2 (C-1), 33.6 (C-5), 32.2(C-4), 29.2 (CH3), 28.3 (C-2), 25.3 (C-3); ESI-MS calcd forC10H20BrNO2 265.07, found 266.12 [M+H]+.
Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 178,p. 571 - 588

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