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[ CAS No. 57561-39-4 ] {[proInfo.proName]}

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Chemical Structure| 57561-39-4
Chemical Structure| 57561-39-4
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Product Citations

Li, Kaixuan ; Wang, Mingqian ; Akoglu, Melike , et al. DOI: PubMed ID:

Abstract: Bruton′s tyrosine kinase (BTK) is a target for treating B-cell malignancies and autoimmune diseases. To aid in the discovery and development of BTK inhibitors and improve clin. diagnoses, we have developed a positron emission tomog. (PET) radiotracer based on a selective BTK inhibitor, remibrutinib. [18F]PTBTK3 is an aromatic, 18F-labeled tracer that was synthesized in 3 steps with a 14.8 ± 2.4% decay-corrected radiochem. yield and ≥99% radiochem. purity. The cellular uptake of [18F]PTBTK3 was blocked up to 97% in JeKo-1 cells using remibrutinib or non-radioactive PTBTK3. [18F]PTBTK3 exhibited renal and hepatobiliary clearance in NOD SCID (non-obese diabetic/ severe combined immunodeficiency) mice, and the tumor uptake of [18F]PTBTK3 in BTK-pos. JeKo-1 xenografts (1.23 ± 0.30% ID/cc) was significantly greater at 60 min post injection compared to the tumor uptake in BTK-neg. U87MG xenografts (0.41 ± 0.11% ID/cc). In the JeKo-1 xenografts, tumor uptake was blocked up to 62% by remibrutinib, indicating the BTK-dependent uptake of [18F]PTBTK3 in tumors.

Keywords: PET imaging ; BTK ; tumor ; fluorine-18 ; Jeko-1 ; U87MG

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Product Details of [ 57561-39-4 ]

CAS No. :57561-39-4 MDL No. :MFCD03425857
Formula : C8H17NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :RFDSJHHLGFFVHD-UHFFFAOYSA-N
M.W : 175.23 Pubchem ID :545700
Synonyms :

Calculated chemistry of [ 57561-39-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.88
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.34
TPSA : 49.77 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.21
Log Po/w (XLOGP3) : 0.43
Log Po/w (WLOGP) : 0.85
Log Po/w (MLOGP) : 0.63
Log Po/w (SILICOS-IT) : -0.07
Consensus Log Po/w : 0.81

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.87
Solubility : 23.8 mg/ml ; 0.136 mol/l
Class : Very soluble
Log S (Ali) : -1.04
Solubility : 15.9 mg/ml ; 0.0907 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.73
Solubility : 32.3 mg/ml ; 0.184 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.13

Safety of [ 57561-39-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 57561-39-4 ]

* 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.

  • Upstream synthesis route of [ 57561-39-4 ]
  • Downstream synthetic route of [ 57561-39-4 ]

[ 57561-39-4 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 109-83-1 ]
  • [ 24424-99-5 ]
  • [ 57561-39-4 ]
YieldReaction ConditionsOperation in experiment
100% at 20℃; for 1 h; To a solution of 2-(methylamino)ethanol (500 mg, 0.53 ml, 6.66 mmol) in CH2Cl2 (20 ml) was added Boc2O (1.48 g, 6.79 mmol), followed by stirring at room temperature for 1 hour.
The reaction solution was extracted with brine and CH2Cl2.
The organic layer thus obtained was dried over MgSO4 and filtered.
Then, the filtrate was concentrated in vacuo to obtain the object compound (colorless oil, quantitative);
1H NMR (200 MHz, CDCl3) δ 3.74 (q, J= 10.5, 5.2 Hz, 2H) 3.25 (t, J= 5.2 Hz, 2H) 2.91 (s, 3H) 1.45 (s, 9H);
mass spectrum m/e (relative intensity) 144 (20) 102 (24) 57 (70) 44 (100).
100% at 20℃; for 4 h; Example 38; N1-(3-Fluoro-4-(2-(1-(2-(methylamino)ethyl)-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N3-(2-methoxyphenyl)malonamide (96); Step 1: tert-Butyl 2-hydroxyethyl(methyl)carbamate (97) (J. Med. Chem., 1999, 42, 11, 2008) To a solution of 2-(methylamino)ethanol (5.0 g, 67 mmol) in THF (50 ml) at RT was added Boc2O (15.7 g, 72 mmol) and the reaction mixture was stirred at RT for 4 hours. The reaction mixture was concentrated to dryness and the title compound 97 was used directly in the next step with no additional purification (11.74 g, 100percent yield). MS (m/z): 176.2 (M+H).
100% at 20℃; for 1 h; Preparation of l-2-[4-Bromo-2-(4-oxo-2-ftιioxo1hiazolidin-5-ylidenemefliyl)phenoxy]efliyl-3-efliyl-l- methylurea(Compoιmd 161)Step 1 : Synthesis of t-butyl2-hydroxyethylmethylcarbamate; To a solution of 2-(methylamino)ethanol (500 mg, 0.53 ml, 6.66 mmol) in CH2Cl2 (20 ml) was added BoC2O (1.48 g,6.79 mmol), followed by stirring at room temperature for 1 hour. The reaction solution was extracted with brine and CH2Cl2. The organic layer thus obtained was dried over MgSO4 and filtered. Then, the filtrate was concentrated in vacuo to obtain the object compound (colorless oil, quantitative);1HNMR (200 MHz, CDCl3) δ 3.74 (q, J= 10.5, 5.2 Hz, 2H) 3.25 (t, J= 5.2 Hz, 2H) 2.91 (s, 3H) 1.45 (s, 9H); mass spectrum m/e (relative intensity) 144 (20) 102 (24) 57 (70) 44 (100).
100% at 0 - 20℃; for 3 h; 2-(methylamino)ethanol (90.1 g, 1.2 mol) was dissolved in 1.2 L of methylene chloride, and BoC2O (218 g, 1 mol) was slowly added thereto while stirring at 00C, followed by at room temperature for 3 hours. The reaction mixture was sequentially washed with 700 mL of an aqueous solution of saturated ammonium chloride, and 300 mL of water. The washed mixture was dehydrated using anhydrous sodium sulfate and concentrated under a reduced pressure, to obtain the compound (a) (175 g, 1 mol, 100percent) as an oil with no color.TLC : Rf = 0.5 (50percent EtOAc in Hex) visualized with Ce-Mo stain1H NMR (600MHz, CDCl3) δ 1.47 (s, 9H), 2.88 (br s, IH), 3.41 (br s, 2H), 3.76 (br s, 2H)
100% at 0 - 20℃; for 3 h; 90.1 g (1.2 mol) of 2-(methylamino)ethanol was dissolved in 1.2 L of methylene chloride, 218 g (1 mol) of Boc2O was slowly added thereto while the resulting solution was stirred at 0°C, and the resulting solution was stirred at room temperature for 3 hours. The reaction mixture was sequentially washed with 700 mL of an aqueous saturated ammonium chloride solution and 300 mL of water, dehydrated using anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 175 g (1 mol) of an achromic oil compound protected by the Boc group (yield: 100percent). [0140] 1H NMR (600MHz, CDCl3) δ 7.84 (br s, 2H), 7.76 (br s, 2H), 4.34 (d, J = 15.0 Hz, 2H), 3.63 (br s, 2H), 3.04 (d, J = 15.0 Hz, 3H), 1.46 (d, J = 16.2 Hz, 9H) [0141] 90 g (0.514 mol) of the obtained compound was dissolved in 1.5 L of tetrahydrofuran, 88.0 g (539 mol) of N-hydroxyphthalimide and 141 g (0.539 mol) of triphenylphosphine were added thereto, 106 mL (0.539 mol) of diisopropyl azodicarboxylate was slowly added thereto while stirring the resulting solution at 0°C, and the resulting solution was stirred for 3 hours while the temperature thereof was raised to room temperature. After concentration of the reaction mixture under reduced pressure, 600 mL of isopropylether was added thereto, the resulting solution was stirred at 0°C for 1 hour, and white solid-type triphenylphosphine oxide was filtered. The solid was washed with 200 mL of isopropylether cooled to 0°C and collected with the first filtrate, and the resulting filtrate was concentrated under reduced pressure to obtain 198 g of a mixture of Compound XX and diisopropyl hydrazodicarboxylate in a mixing ratio of 10 to 15percent (yield: 120percent). [0142] 1H NMR (600MHz, CDCl3) δ 7.84 (br s, 2H), 7.76 (br s, 2H), 4.34 (d, J = 15.0 Hz, 2H), 3.63 (br s, 2H), 3.04 (d, J = 15.0 Hz, 3H), 1.46 (d, J= 16.2 Hz, 9H)
100% at 0 - 20℃; Preparation of Compound XX 90.1 g (1.2 mol) of 2-(methylamino)ethanol was dissolved in 1.2 L of methylene chloride, 218 g (1 mol) of Boc2O was slowly added thereto while the resulting solution was stirred at 0° C., and the resulting solution was stirred at room temperature for 3 hours. The reaction mixture was sequentially washed with 700 mL of an aqueous saturated ammonium chloride solution and 300 mL of water, dehydrated using anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 175 g (1 mol) of an achromic oil compound protected by the Boc group (yield: 100percent). [0152] 1H NMR (600 MHz, CDCl3) δ 7.84 (br s, 2H), 7.76 (br s, 2H), 4.34 (d, J=15.0 Hz, 2H), 3.63 (br s, 2H), 3.04 (d, J=15.0 Hz, 3H), 1.46 (d, J=16.2 Hz, 9H)
100% With triethylamine In dichloromethane at 20℃; for 16 h; Boc2O (8.0 g, 36.6 mmol, 1.1 eq.) and triethylamine (6.75 g, 66.5 mmol, 2.0 eq.) were added to a solution of 2-(methylamino)ethanol (2.5 g, 33.3 mol, 1.0 eq.) in dichloromethane (50 mL).
The reaction was stirred at 20° C. for 16 hours and washed with water (30 mL*2) and brine (30 mL).
The organic phase was dried over anhydrous sodium sulfate, and concentrated to give the title compound (5.8 g, yield: 100percent).
99% at 20℃; for 3 h; Cooling with ice In a 100 mL round-bottom flask, 1.1 mL (13.62 mmol) of 2-(methylamino)ethanol were dissolved in 10 mL of anh. dichloromethane. The reaction flask was then cooled in an ice bath and a solution of 2.5 g (11.4 mmol) of Boc anhydride in 3.6 mL of dichloromethane was added. The reaction mixture was stirred for 3 h at rt. Afterwards, dichloromethane was added to the crude reaction mixture and the organic phase was washed first with 8 mL of a saturated solution of NH4Cl and then with 4 mL of water. The organic phase was washed over anh. Na2SO4, filtered, and concentrated under reduced pressure to yield 1.97 g of 2-[N-(tert-Butyloxycarbonyl)-N-methylamino]ethanol as a colorless oil in 99percent yield. Rf=0.4 (Hex: EtOAc (1:1)). 1H NMR (300MHz, CDCl3) δ (ppm): 3.72 (t, 2H, J=5.2 Hz, H1), 3.37 (d, 2H, J=5.4 Hz, H2), 2.90 (s, 3H, N CH3), 2.59 (br s, 1H, OH), 1.44 (s, 9H, 3 x CH3, tBu); 13C NMR (75 MHz, CDCl3) δ (ppm): 157.1 (CO), 79.7 (Cq, t-Bu), 61.1 (C1), 51.2 (C2), 35.3 (N-CH3), 28.0 (3 x CH3, tBu).
97% With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 4.5 h; A 100 mL round-bottomed flask (rbf) equipped with a magnetic stirbar was charged withTHF (15 mL), water (15 mL) and 2-(methylamino)ethanol (2.00 mL, 25.0 mmol). To thestirred solution exposed to air Boc2O (5.9 g, 27 mmol) was added in 4 portions within 10min resulting in gas evolution. Several drops of sat. aq. NaHCO3 were added 40 min laterto keep the pH around 8. Most of THF was removed on a rotary evaporator 4.5 h after theBoc2O addition. The residue was transferred into a separatory funnel using EtOAc,washed with aq. 2.5 M NH4Cl (20 mL) and brine. The organic phase was dried overMgSO4, filtered into a 500 mL rbf and stripped of volatiles on the rotary evaporator.Using hexane transferred the crude product into a pre-weighed 100 mL rbf, removedvolatiles on the rotary evaporator (20 mm Hg). N-Methyl-N-Boc-aminoethanol wasobtained as colorless oil: 4.26 g (97percent). A 3-neck rbf equipped with a magnetic stirbar, arubber septum, a glass stopcock (Teflon tape, central neck) and connected to a vacuumline was charged with 4.26 g of the protected amine (24.3 mmol). After evacuation andrefill with nitrogen 90 mL of THF freshly distilled from sodium-benzophenone ketyl wasadded. The flask was placed in an ice-water bath. Approx. 25 min later quickly added1.09 g of 60percent NaH (27.2 mmol) in paraffin via the central neck. Approx. 20 min lateradded allyl bromide (2.15 mL, 24.8 mmol) with a syringe via the rubber septum followedby 0.4487 g of tetrabutylammonium iodide (1.21 mmol, 5 molpercent) via the central neck.Approx. 2.5 h later removed the cold bath and let the reaction mixture stirring for 16 hunder nitrogen. The flask was immersed in ice-water bath followed by careful addition ofwater (20 mL, audible sound). The mixture was transferred into a 250 mL separatoryfunnel followed by addition of EtOAc (50 mL) and extraction. The organic phase was setaside and the aqueous phase was extracted with fresh portion of EtOAc (40 mL). Theorganic phases were combined, washed with aq. 2.5 M NH4Cl (50 mL) and brine, driedover MgSO4, filtered into a 500 mL rbf and stripped of volatiles on the rotary evaporatorleaving behind yellow oil, which was chromatographed on silica (normal phase, EtOAchexane,1:3) furnishing 3.7916 g of N-Methyl-N-Boc-aminoethanol O-allyl ether ascolorless oil (72percent yield). N-Boc deprotection was achieved according to the method ofStrazzolini et al.1 To a 200 mL rbf charged with a magnetic stirbar and CH2Cl2 (22 mL)and immersed in an ice-water bath added 1.48 mL of conc. H2SO4 (assumed to be 17.9 M,26.5 mmol) with stirring. The central neck was plugged with a glass stopcock while adropping funnel was attached to the side-neck. A solution of 3.79 g of N-Methyl-N-BocaminoethanolO-allyl ether (17.6 mmol) in 65 mL CH2Cl2 was added to the solution ofacid dropwise from the addition funnel within 45 min followed by removal of cold bathand stirring at rt for 6 h. The dark purple mixture was transferred into a separatory funneland extracted with water (40 mL). The organic phase was extracted with additional 40mL of water, after which the aqueous extracts were combined in a 200 mL Erlenmeyerflask and basified by addition of NaOH (3.245 g in 15 mL water) with stirring. Theresulting solution was saturated with NaCl and extracted with three 50 mL portions ofCH2Cl2. Combined extracts were dried over Na2SO4, filtered into a 500 mL rbf andstripped of the solvent on the rotary evaporator (200 mm Hg). The resulting yellowish oilwas fractionated in vacuo using a one-piece distillation head and a receiving flask held at-50 °C. The title compound was obtained as colorless oil (1.2208 g, 60percent yield).
97% at 20℃; for 0.166667 h; N-methylethanol (6.0 g, 0.08 mol) was added to alumina (12.4 g, 0.12 mol). Then 9.6 g (0.09 mol, 1 .1 eq) of (Boc) 2O were added. The reaction was stirred for 10 min at room temperature. The residue was diluted in EtOAc (2x150 mL), filtered and evaporated. Mono protected compound (13.6 g, 97percent) was obtained as an oil. Rf : 0.25 (cyclohexane/EtOAc 8:2). 1H NMR (300 MHz, CDCl3): 3.72 (t, 2H, J = 5,2 Hz, H2), 3.37 (d, 2H, J = 5,4 Hz, H1 ), 2.90 (s, 3H, H3), 2.59 (bs, 1 H, OH), 1 .44 (s, 9H, (CH3)3). 13C NMR (75 MHz, CDCl3) : 157.1 (C4), 79,7 (C(CH3)3), 61 .1 (C2), 51 .2 (C1 ), 35.3 (C3), 28.0 ((CH3)3). MS (IC/NH3): m/z = 176 [M+H]+
97% With aluminum oxide In ethyl acetate at 20℃; for 0.166667 h; A.
Synthesis of 2-[N-(tert-butyloxycarbonyl)-N-methylamino]ethanol
N-methylethanol (6.0 g, 0.08 mol) was added to alumina (12.4 g, 0.12 mol).
Then 9.6 g (0.09 mol, 1.1 eq) of (Boc) 20 were added.
The reaction was stirred for 10 min at room temperature.
The residue was diluted in EtOAc (2x150 mL), filtered and evaporated.
Mono protected compound (13.6 g, 97percent) was obtained as an oil.
Rf : 0.25 (cyclohexane/EtOAc 8:2).
1H NMR (300 MHz, CDCl3): 3.72 (t, 2H, J = 5,2 Hz, H2), 3.37 (d, 2H, J = 5,4 Hz, H1), 2.90 (s, 3H, H3), 2.59 (bs, 1H, OH), 1.44 (s, 9H, (CH3)3).
13C NMR (75 MHz, CDCl3) : 157.1 (C4), 79,7 (C(CH3)3), 61.1 (C2), 51.2 (C1), 35.3 (C3), 28.0 ((CH3)3).
MS (IC/NH3): m/z = 176 [M+H]+.B. Synthesis of 2-[N-(tert-butyloxycarbonyl)-N-methylamino]ethanol [0128] N-methylethanol (6.0 g, 0.08 mol) was added to alumina (12.4 g, 0.12 mol). Then 9.6 g (0.09 mol, 1.1 eq) of (Boc)2O were added. The reaction was stirred for 10 min at room temperature. The residue was diluted in EtOAc (2x150 mL), filtered and evaporated. Mono protected compound (13.6 g, 97percent) was obtained as an oil. Rf : 0.25 (cyclohexane/EtOAc 8:2).1H NMR (300 MHz, CDCl3): 3.72 (t, 2H, J = 5,2 Hz, H2), 3.37 (d, 2H, J = 5,4 Hz, H1), 2.90(s, 3H, H3), 2.59 (bs, 1H, OH), 1.44 (s, 9H, (CH3)3).13C NMR (75 MHz, CDCl3) : 157.1 (C4), 79,7 (C(CH3)3), 61.1 (C2), 51.2 (C1), 35.3 (C3), 28.0 ((CH3)3).MS (IC/NH3): m/z = 176 [M+H]+.
97% With aluminum oxide In dichloromethane at 20℃; for 0.166667 h; Inert atmosphere N-methylethanol (6.0 g, 0.08 mol) was added to alumina (12.4 g, 1.5 eq), followed by (Boc)2O (9.6 g, 1.1 eq) in DCM (150 mL). The reaction was stirred for 10 min at room temperature. The residue was diluted in EtOAc, filtered and evaporated. Mono-protected compound (13.6 g, ρ=97percent) was obtained as an oil. Rf (EtOAc/Cyclohexane 20percent)=0.25 1H NMR (300MHz, CDCl3): 3.72 (t, 2H, J=5.2Hz), 3.37 (d, 2H, J=5.4Hz), 2.90 (s, 3H), 2.59 (bs, 1H), 1.44 (s, 9H). 13C NMR (75MHz, CDCl3): 157.1, 79.7, 61.1, 51.2, 35.3, 28.0. MS (IC+): m/z=176 [M+H+], calculated 176.
97% at 0 - 20℃; A solution of 2-(methylamino)ethanol (9.01 g, 120 mmol, 1.20 eq.) in dichloromethane (50 mL) was cooled to 0 °C followed by dropwise addition of a solution of di-tert-butyl dicarbonate (21.83 g, 100.00 mmol, 1.00 eq.) in dichloromethane (40 mL) over a period of 1 h. The reaction mixture was stirred overnight at room temperature. After removal of the solvent under reduced pressure, brine (35 mL) was added and the resulting aqueous phase was extracted with ethyl acetate (5 × 30 mL). The collected organic layers were washed with brine (2 × 30 mL) and dried over MgSO4. Removal of the solvent under reduced pressure afforded BocN-MP as a pale yellow oil (17.00 g, 97.02 mmol, 97percent). 1H-NMR (300 MHz, CDCl3, 300 K): δ (ppm) = 1.45 (s, 9H, C(CH3)3), 2.91 (s, 3H, NCH3), 3.38 (t, 2H, HOCH2CH2N), 3.73 (t, 2H, HOCH2CH2N).
97%
Stage #1: for 0.666667 h;
Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 4.5 h;
Di-tert-butyl dicarbonate (5.9 g, 27.03 mmol) was added to the mixture in THF, distilled water and 2-methylamino ethanol (2 ml, 24.90 mmol) After stirring for 40 minutes, saturated aqueous NaHCO3 solution was added to adjust pH to 8. Thereafter, the mixture was stirred at room temperature for 4 hours and 30 minutes. The reaction was terminated by evaporation of THF, followed by addition of EtOAc, washing with 2.5 M Ammonium chloride and aqueous NaCl solution, and drying over MgSO4. EtOAc was evaporated and redissolved in hexane and evaporated, and the reaction product (Boc-methylamino ethanol) was dried in a vacuum oven (yield = 97percent).
92% With triethylamine In dichloromethane at 20℃; for 2 h; Synthesis of 219.1 To a solution of 2-(methylamino)ethanol (750 mg, 10 mmol, 1.0 eq) and Et3N (1.1 g, 11 mmol, 1.1 eq) in DCM (100 mL), Boc20 (2.3 g, 10.5 mmol, 1.05 eq) was added. The mixture was stirred at room temperature for 2 h and then washed with H20 (80 mL x 3). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 219.1 (1.6 g, yield: 92percent) as a yellow oil; ESI-MS (M+H)+: 176.2.
90% at 20℃; for 2 h; Cooling with ice bath Example 82Synthesis of te/*-butyl 2-(4-isocyanatophenoxy)ethyl(methyl)carbamate[00236] To a mixture 2-(methylamino) ethanol (5.0 g, 66.5 mmol) in 15ml of ethyl acetate was added a solution of (BoC)2O (14.5 g, 66.5 mmol) in 5 mi of ethyl acetate dropwise with cooling in an ice bath The resulting mixture was stirred at room temperature for 2 hours, and the solvent was removed by evaporation under reduced pressure. The residue was dissolved in ethyl acetate, washed with water, dried over Na^SO4 and filtered. After removing the solvent, the crude tert-butyl 2-hydroxyethyl(methyl)carbamate was used without further purification for the next reaction (10.5 g, 90percent) A solution of diisopropyl azodicarboxylate (5.22 g, 25.9 mmol) in 5 ml of THF was added dropwise to a solution of 4-nitryl phenol (3.0 g, 21 56 mmol), tert-butyl 2-hydroxyethyl(methyl)carbamate (4.53 g, <n="101"/>25.9 minol) and triphenylphosphine (6.78 g, 25.9 mtnol) in 60 ml of THF with ice-bath cooling under nitrogen atmosphere. The resulting mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure by evaporation. The residue was mixed with ether and filtered. The filtrate was concentrated and purified by flashing silica gel column (Petroleum ether/Ethyl acetate=10/l~8/l) to afford the intermediate /ert-butyl methyl(2-(4-nitrophenoxy)ethyl)carbamate (2.48 g. 39percent) To a solution of this intermediate tert-butyl methyl(2-(4- nitrophenoxy)ethyl)carbamate (2.48 g, 8.4 mmol) in methanol was added Pd/C under hydrogen atmosphere. The mixture was heated to 50 0C for 1 hour, and then cooled down to room temperature and filtered. The filtrate was concentrated to give the crude tert-butyl 2-(4-amuiophenoxy)ethyl(methyl)carbamate which was used without further purification for the next reaction (2.10 g, 95percent). To a solution of tπphosgene (206 mg, 0.695 mmol) in DCM was added tert-butyl 2-(4-aminophenoxy)ethyl(methyl)carbamate (500 mg, 1.88 mmol) with ice-bath cooling followed by dropwise addition of TEA (380 mg, 3,76 mmol). After that, the mixture was stirred at room temperature for 2 hours. Tbe solvent was removed under reduced pressure without heating. The residue mixed with ether and filtered, The filtrate was concentrated to give tert-butyl 2-(4-isocyanatophenoxy)ethyl(methyI)carbamate (500 mg).
86% at 20℃; for 2 h; Step 1:
To a mixture of 2-(methylamino)ethanol (5.0 g, 66.6 mmol) in DCM (100 mL) was added a solution of (Boc)2O (15.0 g, 67.9 mmol) in DCM (20 mL).
The mixture was stirred at rt for 2 h, diluted with EA (100 mL) and washed with water.
The organic layer was separated, dried over Na2SO4, filtered and concentrated to give tert-butyl 2-hydroxyethyl(methyl)carbamate 112a (10.0 g, 86percent) as colorless oil.
78% at 0 - 20℃; for 2 h; A solution of Boc2O (5.80 g, 26.6 mmol) in dry EtOAc (10 ml) was added dropwise to a 0 °C cooled solution of 2-(methylamino)ethanol (2.14 ml, 26.6 mmol) in dry EtOAc (9 ml).
The mixture was stirred at room temperature for 2 h, and then concentrated under reduced pressure.
The oil residue was partitioned between EtOAc (100 ml) and water (300 ml), and the collected organic phases dried over anhydrous Na2SO4, filtered and evaporated in vacuum to furnish t-butyl 2-hydroxyethyl(methyl)carbamate in 78percent yield (3.66 g) of as a colorless oil. IR (liquid film, cm-1): 3444, 2977, 1673, 1394, 1225, 1156, 1074, 877, 774. 1H NMR (CDCl3) δ 3.72-3.80 (m 3H), 3.40 (t, J = 5.0, 2H), 2.92 (s, 3H), 1.47 (s, 9H).
66% With dmap; triethylamine In dichloromethane at 20℃; for 17 h; A mixture of 2-(methylamino)ethanol (2.0 g, 27 mmol), triethylamine (4.4 mL, 33 mmol), di-tert-butyl dicarbonate (6.1 g, 28 mmol) and 4-dimethylaminopyridine (160 mg, 1.3 mmol) in CH2C12 (200 mL) was stirred at ambient temperature. After 17 h, the reaction mixture was diluted with H20 (50 mL). The aqueous layer was separated and extracted with CH2Cl2 (25 mL). The combined organic layers were washed with saturated NaCl (25 mL) , dried (Na2S04) and concentrated under reduced pressure. Purification by column chromatography (silica gel, 75: 25 CH2Cl2/MeOH) gave tert-butyl (2- hydroxyethyl) methylcarbamate (3.1 g, 66percent) as a colorless oil: 1H NMR (300 MHz, DMSO-d6) 81.38 (9H, s), 2.80 (3H, br s), 3.17 (2H, t, J = 8.8 Hz), 3.42-3.48 (2H, m), 4.65 (1H, br s).
62% With dmap In acetonitrile at 20℃; for 16 h; A mixture of 2-methylamino-ethanol (2.5 g; 33.3 mmol; 1 eq.), di-tert-butyl dicarbonate (7.99 g; 36.6 mmol; 1.1 eq.) and dimethyl-pyridin-4-yl-amine (813 mg; 6.66 mmol; 0.2 eq.) in ACN (50 mL) and the resulting mixture was stirred at room temperature for 16 hours. After dilution with EA, the solution was washed with sat. aq. NH4CI, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (25percent to 70percent EA in cyclohexane) afforded the title compound (4 g, 62percent) as a colourless oil. 1H NMR (DMSO-de) δ 4.70-4.61 (m, 1 H), 3.46 (q, J = 5.8 Hz, 2H), 3.18 (t, J = 6.1 Hz, 2H), 2.80 (br s, 3H), 1.38 (br s, 9H).
13.29 g at 20℃; for 48 h; Inert atmosphere 2-(Methylamino)ethanol (5.32 ml, 66.6 mmol) was dissolved in dry dichioromethane (DCM) (30 ml). Boc2O (17.00 ml, 73.2 mmol) was added portion-wise and reaction mixture stirred under N2 at rt. The reaction mixture was left stirring at rt for a further 2 days. The reaction mixture was diluted with water, the organic layer separated and the aq. layer further extracted with DCM. The combinedorganic layers were dried (Na2SO4) and concentrated to give the product (13.29 g, 76 mmol, 114percent)as a colourless oil. LCMS (2 mm Formic): Rt = 0.66 mi [MH] = 176.
6.6 g With potassium carbonate In water at 20℃; for 16 h; To a stirred suspension of 2-(methylamino)ethanol (5.0 g) in water (75 mL)was added potassium carbonate (15.3 g) and di-tert-butyl dicarbonate (12.1 g)and the mixture was stirred at room temperature for 16 hours. The mixture was extracted with dichloromethane. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Aminophase-silica-gel chromatography gave 6.6 g of thetitle compound.
66.19 g at 20℃; for 2 h; Cooling with ice Reference Example 1 tert-Butyl 2-hydroxyethyl(methyl)carbamate (0384) (0385) To a mixture of 2-(methylamino)ethanol (30.04 g) and ethyl acetate (90 mL) was dropwise added a mixture of di-tert-butyl dicarbonate (87.30 g) and ethyl acetate (10 mL) under ice-cooling. After stirring at room temperature for 2 hrs., the mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (150 mL), washed with water (100 mL) and dried over anhydrous magnesium sulfate. Concentration under reduced pressure gave the title compound (66.19 g) as a colorless oil. (0386) 1H-NMR (CDCl3): 1.47 (9H, s), 2.92 (3H, s), 3.40 (2H, t, J=5.1 Hz), 3.72-3.80 (2H, m).
2.4 g With triethylamine In dichloromethane at 20℃; TEA (3.52 mL, 25.00 mmol) was added to a solution of Boc2O (3.00 g, 13.77 mmol) and 2-(methylamino)ethanol (1.00 mL, 12.52 mmol) in DCM (80 ml) and stirred at rt overnight. The mixture was washed with brine, dried on MgSO4, filtrated and concentrated to afford 2.40 g of intermediate 158 (colorless oil).
20 g at 25℃; for 16 h; To a solution of 2-(methylamino)ethanol (10 g, 133.14 mmol) in DCM (10 mL) was added B0C2O (34.87 g, 159.77 mmol) at 25 °C. The mixture was stirred at 25°C for 16 hrs and then concentrated. The residue was purified by column chromatography to afford ie/t-butyl N-(2- hydroxyethyl)-N-methyl-carbamate (20 g, Compound BE-1) as a colorless oil.

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YieldReaction ConditionsOperation in experiment
100% With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 3 h; (a) tert-Butyl methyl(2-oxoethyl) carbamate; Dess-Martin periodinane (22 g, 52 mmol) was added in portions to 2-(N-Boc- methylamino)ethanol (8.8 g, 50 mmol) in dicholoromethane at O0C. The mixture was allowed to reach r.t. and stirred for 3h. Saturated solutions of aqueous sodium hydrogencarbonate and sodium thiosulfate were added and the resulting solution stirred for 0.5 h. The organic phase was separated and washed with saturated sodium hydrogencarbonate solution, dried over magnesium sulfate and concentrated to give 9 g (quantitative yield) of the title compound. GC-MS m/z 174 (M +1).
98% With Dess-Martin periodane In dichloromethane at 20℃; for 3 h; Inert atmosphere To an ice-cooled solution of tert-butyl 2-hydroxyethyl(methyl)carbamate (300mg, 1 .71 mmol)) in dry CH2CI2 (8.5ml_) under argon was added portion wise Dess-Martin periodinane (762mg, 1.8mmol). Once finished the addition, the reaction mixture was stirred at room temperature for 3h. The mixture was poured into saturated solutions of NaHCOs (50 mL) and Na2S203 (50 mL) and more CH2CI2 (100 mL). It was well-stirred at room temperature for 30 minutes. The organic phase was separated and washed with sat. aq. NaHC03 (1 x 20 mL). It was dried over magnesium sulphate and concentrated to afford the title compound (370 mg, 98percent) as colourless oil together with a yellow solid, which was used in the next step without further purification.1H NMR (300 MHz, cdcl3) δ 9.61 (s, 1 H), 3.98 (d, J = 33.9 Hz, 2H), 2.94 (t, J = 10.8 Hz, 3H), 1 .46 (dd, J = 8.2, 6.3 Hz, 9H).
74%
Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -60℃; for 0.166667 h;
Stage #2: With triethylamine In dichloromethane at -60℃; for 0.5 h;
Route ASynthesis of compound 1: 7.5 ml (85 mmol) oxalyl chloride was dissolved in 200 ml DCM and cooled to T < -60 °C and 12.1 ml (171 mmol) DMSO in 10 ml DCM was added dropwise (T < -60 °C) and stirred an additional 10 min. 10.0 g (57 mmol) N-Boc-N-methylaminoethanol in 40 ml DCM were added dropwise (T < -60 °C) and stirred an additional 10 min. 40 ml (285 mmol) Et3N was added dropwise followed by 50 ml DCM (T < -60 °C) and stirred for 30 min. The reaction mixture was warmed to 0 °C and washed with 3x100 ml water, 100 ml 0.5 M KHS04, 75 ml brine, dried with MgS04 and concentrated in vacuo. The product was purified by column chromatography (Si02, DCM/ethyl acetate, 1 :0 to 9: 1) to give 7.36 g (74percent) of compound 1. 1H-NMR (300MHz, CDC13): δ = 1.42/1.46 (s, 9H, Boc), 2.93/2.96 (s, 3H, Me), 3.90/4.01 (s, 2H, CH2), 9.60 (s, 1H, CHO). Z/E isomers.
200 g
Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at 65℃; for 1 h; Inert atmosphere
Stage #2: With triethylamine In dichloromethane at -70℃; for 3 h; Inert atmosphere
A flame-dried 3 L, 3-neck round bottom flask containing a mechanical stirrer (central port), internal temperature probe and addition funnel was charged with oxalyl chloride (176 mL, 2.01 mol) and CH2Cl2 (634 mL). The flask was cooled to -70 °C and DMSO (286 mL, 4.02 mol) was added over 2.5 h at a rate that maintained an internal temperature below -65 °C. The mixture was then stirred for an additional 15 min, after which tert-butyl 2-hydroxyethyl(methyl)carbamate12 (235 g, 1.34 mol) in CH2Cl2 (700 mL) was added over 1 h, followed by slow addition of Et3N (841 mL, 6.04 mol) over 30 min. Both of these reactants were added at a rate that did not cause an increase in internal temperature. After addition of the alcohol solution the reaction was cloudy. Upon initial addition of Et3N the reaction became colorless/clear however at the end the reaction was milky white. The reaction was monitored by TLC (Hex/EtOAc 1:1) until the reaction was deemed complete (2.5 h additional, -70 °C). Saturated aqueous sodium bicarbonate solution (500 mL) was then introduced to quench the reaction at -78 °C. (Note: Quenching is fairly exothermic and thus should be done slowly.) The reaction was warmed to rt and the phases were separated. The combined organics were washed with water, dried over MgSO4, and concentrated (upon concentration, some small amounts of precipitate (presumably Et3N/HCl salt) were observed however this small amount did not impede distillation or effect final purity.) Distillation (87-89 °C, 3 mmHg) provided aldehyde 2 (200 g, 128 mmol) as a colorless oil, which matched all data reported by Kato and co-workers.12

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