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[ CAS No. 153086-78-3 ]

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CAS No. :153086-78-3 MDL No. :MFCD03788155
Formula : C11H24N2O4 Boiling Point : 365.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :248.32 g/mol Pubchem ID :9881394
Synonyms :

Safety of [ 153086-78-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
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[ 153086-78-3 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 929-59-9 ]
  • [ 24424-99-5 ]
  • [ 153086-78-3 ]
YieldReaction ConditionsOperation in experiment
100% at 0 - 20℃; for 23 h; Inert atmosphere General procedure: The diamine 10 (1 equiv) in DCM solution (10 mL / mmol) was treated with Boc2O in default (0.15 equiv) for 5 h at 0 °C and 18 h at room temperature. The organic phase was washed with water, until all the unreacted 10 was extracted. The Boc-protected compound 11 was quantitatively recovered after drying (MgSO4) and concentration under vacuum. 11a: 1H NMR (300 MHz, CDCl3): d 1.45 (s, 9H), 1.80 (br m, 2H, NH2), 3.25 (m, 2H), 3.38 (m, 2H), 3.50-3.70 (m, 8H), 5.10 (br s, 1H, NHCO2). 11b: 1H NMR (300 MHz, CDCl3): d 1.42 (s, 9H), 1.75 (br m, 2H, NH2), 2.84 (t, 2H, J = 5.3 Hz), 3.29 (m, 2H), 3.51 (m, 4H), 3.58 (sharp m, 8H), 5.30 (br s, 1H, NHCO2).
99% at 20℃; Based on literature39 ethylenedioxy-bis-ethylamine (8.90mL, 61.00mmol, 6.0 eq.) was dissolved in DCM p.a. (60mL) and di-tert-butyldicarbonate (2.20g, 10.10mmol, 1.0 eq.) dissolved in DCM p.a. (20mL) was added dropwise over the timespan of 2h. After stirring the solution overnight at rt, the solvent was removed and the residue dissolved in water (20mL). The aq. phase was extracted with DCM p.a. (4×25mL). Afterwards the combined organic layer were dried over MgSO4 and the solvent was removed to yield the product as a colorless oil. Yield: 2.51g, 10.00mmol, 99percent. 1H NMR (300MHz, CDCl3): δ/ppm=3.60 (s, 4H), 3.56–3.48 (m, 4H), 3.30 (q, J=5.2Hz, 2H), 2.87 (t, J=5.2Hz, 2H), 1.56 (s, 2H), 1.43 (s, 9H). 13C NMR (75MHz, CDCl3): δ/ppm=155.9, 77.4, 77.0, 76.6, 73.4, 70.1, 41.7, 40.3, 28.4. MS-ESI+ (MeOH): calculated: m/z=249.1809 [M+H]+; measured: m/z=249.1823 [M+H]+
98% at 20℃; for 18 h; General procedure: Boc-protected linkers were prepared by the dropwise addition of a diluted solution of di-tert-butyl dicarbonate in anhydrous DCM to the corresponding diamine precursor dissolved in DCM in an ice chilled round bottom flask. The reaction mixture was stirred at room temperature for 18 h after which the volatiles were evaporated. The as-formed residue was extracted dissolved in aqueous NaHCO3 and extracted with DCM. The organic aliquot was collected, dried over anhydrous MgSO4, and concentrated in vaccuo.
97% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1 h; To a solution of 1,2-bis(2-aminoethoxy)ethane (0.815 g, 5.5 mmol) and DIPEA (0.31 mL, 1.8 mmol) in anhydrous CH2Cl2 (10 mL) at room temperature was dropwise added to solution of Boc2O (0.400 g, 1.8 mmol) in anhydrous CH2Cl2 (5 mL). After stirring for 1 h, the mixture was concentrated and purified by column chromatography (silica, DCM/MeOH=4:1). The collected fraction was concentrated, dissolved in CHCl3 and filtered. The filtrate was concentrated again to afford 4 as a colorless oil (0.440 g, 97 percent).
93% at 0 - 20℃; 3. Synthesis of puromycin-jeffamine intermediate (Scheme III) . A solution of BOC anhydride (Sigma, 361941) in chloroform (138 mL) was added to a solution of the jeffammine in chloroform (229 mL) maintaining at 0-5 °C. The addition was completed in 30 min. The reaction was slowly warmed and stirred at 18-20°C o/n. The day after the reaction was dissolved in DCM (400 mL) and washed with brine, dried (MgS04) and evaporated at 40°C to a clear oil (~ 93 percent final efficiency)
86% at 20℃; for 5 h; Boc anhydride (1.000 g, 1.053 mL, 4.582 mmol) in DCM (5.00 mL) was added portion wise over 2 h at room temperature to 2,2(ethylenedioxy)bis(ethylamine) (4.074 g, 4.01 mL, 27.489 mmol) in DCM (10.00 mL).
This was further stirred at room temperature for 5 h and solvent was removed.
Water (30.00 mL) was added to the residue and extracted with DCM (6*20.00 mL), the combined organic extracts were dried (MgSO4) and concentrated in vacuo to yield the linker Tert-butyl (2-(2-(2-aminoethoxy)ethoxy)ethyl)carbamate (6) as pale yellow oil (0.982 g, 3.957 mmol, 86percent).
85% at 20℃; for 12.5 h; Reaction Step 1:; Preparation of 8-N-Boc-3,6-dioxaoctaneamine To a solution of 163 g (1100 mmol) of 3,6-dioxa-1,8-octanediamine in 700 mL CHCl3 was added 8.00 g (36.65 mmol) of di-tert-butyl dicarbonate in 100 mL CHCl3 with stirring at ambient temperature over 30 minutes. The mixture was stirred for 12 hours, washed with (8.x.100 mL) water, dried over anhydrous Na2SO4, and concentrated under reduced pressure to yield 8.62 g (85percent) of the desired product as a colorless oil. 1H NMR (CDCl3, δ) 5.40 (s, 1H, CONH), 3.63 (m, 4H, OCH2), 3.54 (m, 4H, OCH2), 3.32 (m, 2H, CH2NHCO), 2.87 (t, 2H, CH2NH2), 1.46 (s, 9H), 1.40 (s, 1H, NH2).; Synthesis of Compound 66 This compound was prepared as previously described for the preparation of N-Boc-4,7,10-trioxatridecane-13-diamine (page 29, line 10).
84% at 0 - 20℃; 1,8-Diamino-3,6-dioxaoctane (69.65 g, 0.47 mol) and tetrahydrofuran were added to a 10 L three-necked flask,After cooling the reaction system to 0 ° C,A solution of Boc anhydride (20.51 g, 0.094 mol) in tetrahydrofuran was added dropwise thereto,After dropping at room temperature,TLC monitoring reaction is completed.The solvent was removed by rotary evaporation tetrahydrofuran,Then add dichloromethane and water,After liquid separation,The organic phase was collected and washed once more with water,The organic phase is then dried over anhydrous sodium sulphate,concentrate,After distillation under reduced pressure, 19.6 g of tert-butyl 2- (2- (2-aminoethoxy) ethoxy) ethylcarbamate was obtained,Yield 84percent.
83% at 0℃; for 3.5 h; To a mixture of 2, 2'-(ethylenedioxy)bis(ethylamine) (153 g, 1.032 mol, 4.5 equiv) in DCM (250 mL) at 0 °C was added a solution of di-tert-butyl dicarbonate (50 g, 0.229 mol, 1 equiv) in DCM (100 mL) over 3.5 h. The mixture was slowly warmed to rt, stirred at rt overnight and washed with 25percent aqueous NaCl solution (3 x 100 mL) and water (100 mL). The organic layer was extracted with 20percent aqueous citric acid (250 mL). The aqueous layer was washed with DCM (150 mL), basified to pH 13-14 by aqueous NaOH solution (2 M), extracted with DCM (3x). The combined organic layers were dried and concentrated to give 47 g (83percent)) of intermediate H.l as clear oil.
75.6% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 8 h; The compound DAB-2 was prepared according to literature method (Bioorganic and a solution of di-tert-butyl dicarbonate ((Boc)2O) (0.7 g, 3.21 mmol) in CH2Cl2 (10 mL) was added dropwise to a mixture of tris(ethylene glycol)-1,8-diamine (5.0 g, 278 mmol) and diisopropylethylamine (10 mL, 57 mmol) at room temperature over a period of 2 hours.
The reaction mixture was stirred for 6 hours, after which it was concentrated in vacuo.
Purification by flash silica gel column chromatography (CH2Cl2/CH3OH, 10/1, v/v) afforded N-Boc-3,6-dioxaoctane-1,8-diamine (0.6 g, 75.6percent).
1H NMR (500 MHz, CDCl3): δ 3.61 (s, 4H), 3.55-3.53 (t, 2H), 3.52-3.49 (t, 2H), 3.31-3.30 (t, 2H), 2.88-2.85 (t, 2H), 1.43 (s, 9H).
74% With hydrogenchloride In methanol at 0 - 20℃; for 0.25 h; A round bottom flask was charged with methanol (MeOH)20 ml was added and weighed.Hydrogen chloride (HCl) gas was bubbled at 0 ° C for 15 minutes.This was stirred at room temperature for 15 minutes.After stirring, weigh out the difference before and after bubbling.A 500 mL round bottom flask was charged with hydrochloric acid (HCl, 0.2 g, 6.74 mmol) dissolved in methanol (MeOH). After that,1,8-Diamino-3,6-dioxaoctane (1 g, 6.74 mmol) was added slowly at 0 ° C.After reacting at room temperature for 15 minutes,The distilled water was slowly added until the ammonium salt completely disappeared. After that,After reaction at room temperature for 15 minutes,(Boc) 2O (1.47 g, 6.74 mmol) was added at room temperature.After that,After 15 minutes of reaction at room temperature,The reaction was terminated,The solvent was removed under reduced pressure and then ether and distilled water were added.After that,After separating only the water layer, 50 ml of 1N sodium hydroxide (NaOH) was added to the water layer.The water layer was washed three or four times with methylene chlorideExtracted with methylene chloride, dried over anhydrous manganese sulfate (MsSO4), filtered, and then decompressed to remove the solventNH- [1,8-Diamino-3,6-dioxaoctane] -Boc (see Fig. 14). The yield was 74percent. NH- [1,8-Diamino-3,6-dioxaoctane] -Boc
72%
Stage #1: With ethyl trifluoroacetate, In methanol at -78℃; for 1 h; Inert atmosphere
Stage #2: at 0 - 20℃; for 3 h;
Stage #3: With ammonia In methanol; water at 50℃; for 8.5 h;
Under argon, ethyl trifluoroacetate (1.7 mL, 14.3 mmol) was added to asolution of 1,2-bis(2-aminoethoxy)ethane (2.00 g, 13.6 mmol) in absolutemethanol (200 mL) at -78°C, and the reaction mixture was stirred for 1 h at thesame temperature. Di-tert-butyl dicarbonate (6.0 mL, 26.1 mmol) was added to the mixture at 0°C, and the reaction mixture wasstirred for 3 h at room temperature. 28percent aqueous NH3 solution (60 mL) was added to the mixture atroom temperature, and then the reaction mixture was stirred at 50°C. After 8.5h, the reaction mixture was evaporated under reduced pressure. Then H2O was added to the mixture, and the solution wasextracted with dichloromethane. The organic layer was evaporated under reducedpressure, and the residue was purified by column chromatography (kanto60N,dichloromethane / methanol / 28percent aqueous NH3 solution, 200 / 5 / 1 to 100 /5 / 1) to afford N-Boc-1,2-bis(2-aminoethoxy)ethane (2.42 g, 72percent) as a paleyellow oil
71% at 0 - 20℃; for 3 h; Toa solution of amine S6 (15 mL,102.7 mmol) in CH2Cl2 (100 mL) was added a solution ofBoc2O (2.184 g, 10.01 mmol) in CH2Cl2 (55 mL +5 mL rinse) dropwise via addition funnel at 0 °C. After the addition wascomplete, the reaction mixture was allowed to warm to RT and after 3 h, itwas quenched with H2O (100 mL). The two layers were separated andthe organic phase was washed with H2O (3 x 50 mL) and brine (50 mL),dried (MgSO4), filtered, and concentrated in vacuo to give 1.775 g (71percent) of S7 as a colorless liquid.TLC: Rf = 0.18 (10percent MeOH, 0.5percent NH4OHin CH2Cl2)1H-NMR (CDCl3, 400 MHz): δ 5.14 (br s,1H), 3.61 (s, 4H), 3.55–3.50 (m, 4H), 3.31 (m, 2H), 2.87 (t, J = 5.2 Hz, 1H), 1.43 (s, 9H) ppm
70% at -78℃; for 13 h; Synthesis of Triazine Libraries Synthesis of the TG-Boc linker (1) for Library 2; <n="38"/>[00209] 2,2'-(Ethylenedioxy)bis(ethylamine) (10 equiv.) was dissolved in dichloromethane and the solution was cooled down to -78 °C in a dry ice/acetone bath. Di- tert-butyl dicarbonate (1 equiv.) was dissolved in dichloromethane and added to the solution of 2,2'-(Ethylenedioxy)bis(ethylamine) dropwise over a period of 3 h in a nitrogen gas atmosphere. The reaction mixture was allowed to stir for 10 h followed by extraction with saturated NaCl solution. The organic layers were combined and dried over MgSO4. The solvent was removed in vacuo (70percent yield).
68% at 20℃; for 8 h; To a solution of 2,2’-(ethylenedioxy)diethylamine (17.78 g, 120 mmol) in dioxane (80 mL) a solution of di-tert-butyldicarbonate (4.36 g, 20 mmol) in dioxane (30 mL) was added over a period of 5 h. The reaction was stirred for 3 h at rt. The solvents were evaporated under reduced pressure. The residue was dissolved in H2O (20 mL) and extracted with DCM (45 mL). The organic layer was washed with saturated aq. NaCl and dried over Na2SO4. The solution was concentrated under diminished pressure and the residue chromatographed on a silica gel column with ethyl acetate-hexane (1:2 2:1, v/v) DCM-methanol-NH3 (80:15:1.5, v/v/v) to give 4 (3.41 g, 68percent) as a colorless syrup. 1H NMR (300 MHz, CDCl3) δ (ppm) 5.21 (br, 1 H, NH), 3.62-3.46 (m, 8 H, CH2-O), 3.32 (q, J = 5.2 Hz, 2 H, CH2-NH), 2.86-2.92 m, 2 H, CH2-NH2), 1.96 (br, 2 H, NH2), 1.45 (s, 9 H, C(CH3)3); 13C NMR (300 MHz, CDCl3) δ (ppm) 155.98 (Boc-CO), 79.33 (Boc-C(CH3)3), 73.17 (CH2-O), 70.15 (CH2-O), 41.57 (CH2-NH2), 40.29 (CH2-NH), 28.36 (Boc-C(CH3)3); MALDI-TOF (m/z) calcd for C11H24N2O4 = 248.17, found 248.96 (M+H+)
64% at 0℃; for 13 h; 2,2'-(ethylenedioxy)bis(ethylamine) was dissolved in dichloromethane and the solution cooled to 0°C. DI-TERT- butyl-dicarbonate (Boc anhydride) was dissolved in dichloromethane and added to the solution of 2, 2'- (ethylenedioxy) bis (ethylamine) dropwise over a period of three hours. The reaction mixture was allowed to stir for ten hours followed by extraction with saturated NaCl solution. The organic layers were combined and dried over MGSO4. The solvent was removed in vacuo. Synthesis of Building Blocks II by Solution Phase Synthesis Synthesis of N-BOC-2,2'-(ETHYLENEDIOXY)BIS(ETHYLAMINE) (TG-BOC) 2,2'- (ETHYLENEDIOXY) bis (ethylamine) (10 equiv. ) was dissolved in dichloromethane and solution was cooled down to 0°C. Di-tert-butyl dicarbonate (Boc anhydride) (1 equiv. ) was dissolved in dichloromethane and added to the solution of 2, 2 - (ETHYLENEDIOXY) BIS (ethylamine) dropwise over a period of 3 hours. The reaction mixture was allowed to stir for 10 hours followed by extraction with saturated NaCl solution. The organic layers were combined and dried over MGS04. The solvent was removed in vacuo (64percent yield).
58% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 8 h; N-Boc-3,6-dioxaoctane-1,8-diamine
A solution of di-tert-butyl dicarbonate (di-Boc) (6 g, 28 mmol, 0.5 equiv) in CH2Cl2 (100 mL) was added dropwise to a mixture of tris(ethylene glycol)-1,8-diamine (7.6 g, 56 mmol) and diisopropylethylamine (10 mL, 57 mmol) at room temperature over a period of 2 hours.
The reaction mixture was stirred for 6 hours, after which it was concentrated in vacuo.
Purification by flash silica gel column chromatography (CH2Cl2/CH3OH, 10/1, v/v) afforded N-Boc-3,6-dioxaoctane-1,8-diamine (4.1 g, 58percent).
1H NMR (300 MHz, CD3OD): δ 3.6 (s, 4H), 3.54 (t, 2H), 3.53 (t, 2H), 3.24 (t, 2H), 2.8 (t, 2H), 1.4 (s, 9H); MALDI HRMS: m/z 271.1641 [M+Na+].
Calcd for C11H24N2NaO4 271.1634.
56% at 21℃; for 24 h; A solution of di-tert-butyl-dicarbonate (1.10 g, 5.00 mmol, 1 eq) in CH2C12 (5 mE) was added dropwise to a solution of2-[2-(2-aminoethoxy)ethoxy]ethanamine (7.32 mE, 50.0 mmol, 10 eq) in CH2C12 (15 mE). The resulting reaction mixture was stirred at 210 C. for 24 h. The CH2C12 was then removed in vacuo to leave a colourless residue. Addition of EtOAc (125 mE) caused formation of a white precipitate, whichwas washed with a saturated solution ofNa2CO3 (3x50 mE), dried over MgSO4, and concentrated in vacuo. Further purification by column chromatography (8:2 CH2C12/ MeOH) thrnished the desired monoprotected amine as a colourless oil (0.69 g, 2.80 mmol, 56percent yield). ‘H NMR (500MHz, CDC13) ö 5.27 (bs, 1H, NH), 3.54-3.52 (m, 4H, OCH2), 3.47-3.42 (m, 4H, OCH2), 3.23-3.22 (m, 2H, NCH2), 2.80 (t, J=5.0, 2H, NCH2), 2.05 (bs, 2H, NH), 1.35 (s, 9H, CH3); ‘3C NMR (125 MHz, CDC13) ö 156.08 (s), 79.09 (s), 73.19 (t),70.21 (t), 70.16 (t), 41.59 (t), 40.32 (t), 28.40 (q), * 1 missing; IR (neat) 3344, 2869, 1692 cm’; HRMS (CI) calcd for C,,H25N204 [M+H] 249.18143, observed 249.18251.
53% With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane at 20℃; for 4 h; 2,2’-[1,2-Ethane-diyl-bis(oxy)]bis-ethaneamine (2 mL, 13.6 mmol) and diisopropylethylamine (2.4 mL, 13.8mmol) were added to a solution of di-tert-butyl dicarbonate (30percent tetrahydrofuran solution) (5.1 mL, 6.2 mmol) in dichloromethane(29 mL), stirred at room temperature for 4 hours, and then the solvent was distilled away under a reducedpressure. The residue was purified by silica gel column chromatography (dichloromethane/methanol/triethylamine (v/v/v)= 18/1/1) to obtain the title compound (810 mg, 53percent) as a pale yellow oily matter.1H NMR (400 MHz, CDCl3) δ 5.13 (1H, br s), 3.62-3.49 (10H, m), 3.33 (2H, br s), 2.88 (2H, t, J = 5.2 Hz), 1.45 (9H, s)
10% at 0 - 20℃; for 2 h; Preparation of compound 57: Compound 57 was synthesized in accordance with or by slight modification of the method set forth in Zuckermann, R. N.; Martin, E. J.; Spellmeyer, D. C; Stauber, G. B.; Shoemaker, K. R; Kerr, J. M.; Figliozzi, G. M.; Goff, D. A.; Siani, M. A.; Simon, R; Banville, S. C; Brown, E. G.; Wang, L.; Richter, L. S.; Moos, W. H. /. Med. Chem. 1994, 37, 2678. To a solution of 2,2 '-(ethylene dioxy)bis-(ethylamine) (4.44 g, 30 mmol) in CH2C12 (100 mL) was added Boc20 solution (6.54 g, 30 mmol pre-dissolved in 40 mL CH2C12) at 0 °C. The reaction was slowly warmed to rt. After 2 h, the reaction was stopped and the mixture was concentrated. The crude product was purified by flash chromatography (20percent EtOH in CH2C12) to give purified product (771 mg, 10percent).

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