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CAS No. : | 164332-88-1 | MDL No. : | MFCD24167474 |
Formula : | C9H18BrNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DMOPZPBTLCZSGL-UHFFFAOYSA-N |
M.W : | 268.15 | Pubchem ID : | 22712752 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.89 |
Num. rotatable bonds : | 8 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 58.85 |
TPSA : | 47.56 Ų |
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) : | -6.84 cm/s |
Log Po/w (iLOGP) : | 2.88 |
Log Po/w (XLOGP3) : | 1.54 |
Log Po/w (WLOGP) : | 1.92 |
Log Po/w (MLOGP) : | 1.4 |
Log Po/w (SILICOS-IT) : | 1.56 |
Consensus Log Po/w : | 1.86 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.94 |
Solubility : | 3.05 mg/ml ; 0.0114 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.15 |
Solubility : | 1.91 mg/ml ; 0.00711 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.04 |
Solubility : | 0.242 mg/ml ; 0.000904 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.78 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | Stage #1: With methanesulfonyl chloride; triethylamine In dichloromethane at 0 - 20℃; for 3 h; Stage #2: With lithium bromide In dichloromethane; acetone at 20℃; |
Alcohol 64 (1 .25 g, 6.09 mmol) was dissolved in DCM (34 mL). The solution was cooled to 0°C and methanesulfonyl chloride (MsCI, 0.80 mL, 10.3 mmol, 1 .7 equiv) was added to the solution followed by Et3N (1.9 mL, 13.4 mmol, 2.2 equiv). After stirring for 3 h at rt, the reaction mixture was diluted with acetone (33 mL) and LiBr (8.9 g, 103 mmol, 17 equiv) was added. The reaction mixture was stirred overnight at rt. After that time, the solvents were evaporated under reduced pressure. The crude residue was diluted with EtOAc and washed with H20 and brine. The organic phase was dried over anhyd Na2S04. The suspension was filtered over cotton and the filtrate concentrated in vacuo. Purification by flash chromatography eluting with PE/Acetone (85:15→ 8:2) gave bromide 65 (1 .60 g, 5.95 mmol, 98percent) as a colourless oil. 1H-NMR (500 MHz, CDCI3): δ 4.91 (s, 1 H), 3.78 (t, 2H), 3.56 (t, 2H), 3.47 (t, 2H), 3.33 (d, 2H), 1 .45 (s, 9H). |
85% | With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 22 h; | Compound 2 (25.6 g, 125 mmol) and carbon tetrabromide (41.4 g, 125 mmol) were dissolved in dry dichloromethane (200 mL) and triphenylphosphine (32.8 g, 125 mmol) was added thereto.After the reaction mixture was stirred at room temperature for 22 hours, the solvent was distilled off under reduced pressure.The crude product was purified by silica gel column chromatography to obtain 28.6 g of Compound 3 as a colorless solid. Yield 85percent. |
70.73% | With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; for 18 h; | To an ice-cold solution of tert-butyl (2-(2-hydroxy)ethoxy)ethylcarbamate(5 g, 24.5 mmol) in dichloromethane (200 mL) was added triphenylphosphine (9.63 g, 36.7 mmol) followed by carbon tetrabromide (12.18 g, 36.7 mmol) at 0 °C. The reaction mixture was warmed to rt and stirred for 18 h. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (60-120 mesh silica) using 5-10percent ethyl acetate in pet-ether to give tert-butyl 3-bromopropylcarbamate (4.9g, 70.73percent) as a light-brown liquid. 1H NMR (400 MHz, CDC13) δ ppm 4.90 (1H, s), 3.77 (2H, t, J=6.0 Hz), 3.55 (2H, t, J=5.2 Hz), 3.46 (2H, t, J=6.0 Hz), 3.32 (2H, q, J=5.2 Hz), 1.44 (9H, s). |
381 mg | With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 72 h; | Example 5-2-1 Preparation of tert-butyl [2-(2-bromoethoxy)ethyl]carbamate200 mg tert-butyl [2-(2-hydroxyethoxy)ethyl]carbamate (0.97 mmol, 1 .0 eq.) and 388 mg tetrabromomethane (1 .17 mmol, 1.2 eq.) were dissolved in 1 .2 mL THF and cooled to 0 . 307 mg triphenylphosphane (1 .17 mmol, 1 .2 eq.) were added. The reaction mixture was stirred at room temperature for 3 d. Hexane was added to form a white precipitate which was filtered off. The filtrate was evaporated under vacuo to provide the crude target compound, which was used without further purification: 381 mg, 1 .42 mmol, 145percent.1H-NMR (400MHz, DMSO-d6): δ [ppm]= 1.34 (s, 9H), 3.04 (q, 2H), 3.38 (t, 2H), 3.54 (t, 2H), 3.66 (t, 2H), 6.76 (t, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With lithium bromide In water; acetone | tert-Butyl 2-(2-bromoethoxy)ethylcarbamate (4) Lithium bromide (7.6 g, 87 mmol) was added to a solution of compound 3 (3.35 g, 8.74 mmol) in 33 mL of acetone and heated in an oil bath at 55-60° C. After 3 hours TLC (1:1 ethyl acetate-hexanes, ceric ammonium molybdate visualization) showed complete disappearance of starting material (3, Rf=0.7-0.8) and appearance of a major new product (4, Rf=0.8-0.9). The reaction mixture was cooled to room temperature and water (~15 mL) was added. The resulting solution was extracted twice with 25 mL portions of ethyl acetate. The combined ethyl acetate extract was washed with water (15 mL), dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation under reduced pressure to give a clear, colorless oil (2.05 g). This material was purified by flash chromatography on 60 g of Silica Gel 60 (230-400 mesh) eluding with 15:85 ethyl acetate-hexanes and collecting ~50 mL fractions. Based on TLC (silica gel, 50:50 ethyl acetate-hexanes, ceric ammonium molybdate visualization), fractions were combined and concentrated under reduced pressure on a rotary evaporator followed by high vacuum to afford tert-butyl 2-(2-bromoethoxy)ethylcarbamate (4) as a clear, colorless oil (1.92 g, 82percent yield) that was homogenous by TLC. Mass spec: m/z=268.4 (100percent), 270.2 (93percent) [M+H]+ 1H NMR (300 MHz, CDCl3): δ 1.4 (s, 9H), δ 3.2-3.8 (m, 8H), and δ 4.9 (br s, 1H). |
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