Structure of 52221-07-5
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 52221-07-5 |
Formula : | C10H18O4 |
M.W : | 202.25 |
SMILES Code : | O=C(O)CCCCC(OC(C)(C)C)=O |
MDL No. : | MFCD24479669 |
InChI Key : | SNOPFBNMUDQLMF-UHFFFAOYSA-N |
Pubchem ID : | 15908937 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
60% | With pyridine; In N-methyl-acetamide; methanol; dichloromethane; | 1-Methyl, 8-tert-butyl 3-oxo-1,8-octanedioate A solution of <strong>[52221-07-5]mono-tert-butyl adipate</strong> (7.8 g, 37.5 mmol) in dichloromethane (175 ml) was treated with oxalyl chloride (9.8 ml, 112.5 mmol) followed by ten drops of dimethylformamide. The reaction was stirred at room temperature for 1 hour. The solvent was evaporated and the residue was dried under vacuum. To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (5.42 g, 37.6 mmol) in dichloromethane (30 ml) at 0° C. was added pyridine (6.1 ml, 75 mmol) followed by the crude acid chloride in a solution of dichloromethane (30 ml). The reaction was stirred at 0° C. for 1 hour and at room temperature for 2 hours. The reaction was then washed with water and dried over anhydrous magnesium sulfate, filtered and concentrated. The crude residue was then dissolved in methanol and refluxed for 3 hours. The solvent was evaporated and the residue was purified by silica gel chromatography to give the title material (5.82 g, 60percent) as an oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium hydroxide; In tetrahydrofuran; ethanol; | Mono-tert-butyl adipate A solution of methyl tert-butyl adipate (9.9 g, 45.8 mmol) in ethanol (70 ml) and tetrahydrofuran (70 ml) was stirred with aqueous sodium hydroxide (1N, 137 ml, 137 mmol) at 0° C. for 2 hours. The mixture was then diluted with water and washed with dichloromethane (2*). The mixture was diluted with dichloromethane and acidified with aqueous hydrochloric acid (1N, 150 ml). The organic layer was separated and the aqueous phase was extracted with dichloromethane. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated to give the title material (7.82 g, 85percent). 1H NMR (C6D6, delta, ppm): 1.48 (9H, s, -OtBu), 1.52 (4H, m, -(CH2)2-), 2.05-2.10 (4H, m, 2*-CH2COO-). |
85% | Step 26-fert-Butoxy-6-oxohexanoic Acid.11CA solution of 11B (10.3 g, 47.6 mmol) and LiOH (1.26 g, 52.8 mmol) in 3:1 :1 MeOH/THF/hbO (50 mL) was stirred at room temperature for 16 h. The " reaction was diluted with EtOAc and washed with saturated aqueous Na2C03. The aqueous layer was separated and acidified with 1 N HCI, then extracted with EtOAc. The combined organics were washed with brine, dried (Na2S04), filtered and concentrated to yield 11 C (8.14 g, yield = 85percent): H NMR (300 MHz, CDCI3) delta 10.67 (br s, 1 H), 2.50-2.10 (m, 4H), 1.65 (m, 4H), 1.44 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; hexane; water; tert-butyl alcohol; | EXAMPLE 1 Synthesis of mono-tert-butyl adipate Ten grams (0.057 mol) of monoethyl adipate and 200 ml (2.081 mols) of tert-butyl alcohol were charged in a glass flask equipped with a stirrer, a dropping funnel, a thermometer, an Oldershaw column and a Dimroth condenser, and 7.73 g (0.069 mol, 1.2 equivalent) of potassium-tert-butoxide was poured thereinto little by little at room temperature. As a result, the reaction mixture generated heat to cause rising of the temperature to 35° C., and white crystals were precipitated in the reaction mixture. Thereafter, the reaction mixture was heated to 83° C. and the reaction was carried out for 16.5 hours, during which ethyl alcohol produced by the transesterification was distilled off together with tert-butyl alcohol, and tert-butyl alcohol in the same amount as the amount of the distilled tert-butyl alcohol was continuously added through the dropping funnel. After completion of the transesterification, tert-butyl alcohol was distilled off under normal pressure, and the residue was allowed to stand for cooling. Then, 80 ml of ice water was added to the residue, followed by separation washing twice with 100 ml of n-hexane. To the resulting aqueous phase was added 3.96 g (0.039 mol, 1.4 equivalent) of sulfuric acid diluted with 20 ml of cold water to liberate the acid. The components in the aqueous phase were analyzed by GC to obtain a peak area ratio of 20:80 of the starting monoethyl adipate and the product mono-tert-butyl adipate. This aqueous phase was subjected to extraction twice with 100 ml of n-hexane, and then the n-hexane phase extracted twice was washed thrice with 10 ml of pure water and thereafter subjected to concentration under reduced pressure. As a result, 7.20 g of mono-tert-butyl adipate of 92percent in purity containing no monoethyl adipate was obtained. The yield in this case was 57percent. Spectrum data of 1H-NMR on the product were as follows. 1H-NMR(CDCl3) 1.48 (9H, s), 1.64-1.68 (4H, m), 2.22-2.27 (2H, m), 2.33-2.40 (2H, m), 9.64 (1H, br). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 20.0℃; | Step 3ferf-Butyl 6-Chloro-6-oxohexanoate. 11A solution of 11C {8.14 g, 40.3 mmol) and oxalyl chloride (3.46 mL, 40.3 mmol) in DC (100 mL) and a catalytic amount of DMF was stirred at room temperature until no H2 gas was evolved. The reaction was concentrated to yield 11 (8.01 g, yield = 90percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.5% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25.0℃; for 2.0h; | To a solution of <strong>[134272-64-3]1-(2-aminoethyl)-1H-pyrrole-2,5-dione hydrochloride</strong> (0.288g, 1.632 minol) in dichloromethane (DCM) (5 ml, 17 vol) was added DIPEA (0.777 ml, 4.45 minol), followed by 6-(tert-butoxy)-6-oxohexanoic acid (0.300 g, 1.483 minol) as a solution in DCM (5 mL, l7vol). Let reaction stir at RT and then charged 2,4,6-tripropyl-1,3,5,2,4,6- trioxatriphosphorinane 2,4,6-trioxide (T3P) (1.78 1 mL, 2.225 minol) into the reaction. The reaction was stirred at RT until consumption of starting materials (2 h). The reaction was quenched with water (10 mL, 34 vol), layers separated and the aqueous layer was extracted once with DCM (10 mL, 34 vol). The combined organic layers were washed with sat?dNaHCO3 (10 mL, 34 vol), brine (10 mL, 34 vol), dried over MgSO4 and filtered. The filtrate was concentrated under vacuum and the resulting light brown oil was purified by silica gel chromatography (hexane to 100percent EtOAc in 20 min,). Fractions containing product were combined and concentrated under vacuum and placed in vacuum to dry for 24 hours to obtain desired product, compound 1 (0.409 g, 88.5percent yield) desired M/Z= 324.38, found M+1=325.4. The proton NMR for compound 1 is shown in FIG. 1. |
A107224 [843666-40-0]
18-(tert-Butoxy)-18-oxooctadecanoic acid
Reason: Derivatives
A104959 [234081-96-0]
10-(tert-Butoxy)-10-oxodecanoic acid
Reason: Derivatives