No renderable structure data available
O=C(NCCOC1C=CC(N)=CC=1)OC(C)(C)CChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | OTAVA-BB 1398878 |
|---|---|
| IUPAC Name | — |
| CAS Number | 159184-15-3 |
| Database ID | 18173954 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
OTAVA-BB 1398878 (CAS 159184-15-3) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 18173954
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
10 reactions · 10 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-efccbec8a57c494590bfd22954029ebeConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(tert-butoxycarbonyl)-2-(4-nitrophenoxy)ethylamine (5.91 g) was dissolved into methanol (200 ml) and subjected to hydrogeration reaction at ambient pressure by adding 10% palladium carbon catalyst (0.5 g). After completion of hydrogeration reaction, excess catalyst was removed by filtration. Filtrate was concentrated under vacuum to obtain N-(tert-butoxycarbonyl)-2-(4-aminophenoxy)ethylamine (5.07 g) as color-less oily substance. (1-3) N-(tert-butoxycarbonyl)-2-(4-aminophenoxy)ethylamine (1.00 g) was dissolved into pyridine (5 ml) and 2,6-dimethoxybenzoic acid chloride (0.87 g) was added into the solution. After being stirred for one hour, the reaction mixture was concentrated under vacuum and residue was dissolved into chloroform (30 ml). The solution was washed with 1N sodium hydroxide aqueous solution (30 ml) followed by saturated sodium chloride (30 ml). Solvent was distilled out and residue was purified by silica-gel column chromatography (ethyl acetate:hexane=1:1) to obtain 4′-[2-(tert-butoxycarbonylamino)ethoxy]-2,6-dimethoxybenzanilide (1.17 g) as white powder. was added into the solution the reaction mixture was concentrated under vacuum and residue was dissolved into chloroform (30 ml) The solution was washed with 1N sodium hydroxide aqueous solution (30 ml) Solvent was distilled out residue was purified by silica-gel column chromatography (ethyl acetate:hexane=1:1)
Source ID: ord-ad248fe92edc4be1b7de9b2b93d61357Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(tert-butoxycarbonyl)-2-(4-nitrophenoxy)ethylamine (5.91 g) was dissolved into methanol (200 ml) and subjected to hydrogeration reaction at ambient pressure by adding 10% palladium carbon catalyst (0.5 g). After completion of hydrogeration reaction, excess catalyst was removed by filtration. Filtrate was concentrated under vacuum to obtain N-(tert-butoxycarbonyl)-2-(4-aminophenoxy)ethylamine (5.07 g) as color-less oily substance. (1-3) N-(tert-butoxycarbonyl)-2-(4-aminophenoxy)ethylamine (1.00 g) was dissolved into pyridine (5 ml) and 2,6-dimethoxybenzoic acid chloride (0.87 g) was added into the solution. After being stirred for one hour, the reaction mixture was concentrated under vacuum and residue was dissolved into chloroform (30 ml). The solution was washed with 1N sodium hydroxide aqueous solution (30 ml) followed by saturated sodium chloride (30 ml). Solvent was distilled out and residue was purified by silica-gel column chromatography (ethyl acetate:hexane=1:1) to obtain 4′-[2-(tert-butoxycarbonylamino)ethoxy]-2,6-dimethoxybenzanilide (1.17 g) as white powder. subjected to hydrogeration reaction at ambient pressure After completion of hydrogeration reaction, excess catalyst was removed by filtration Filtrate was concentrated under vacuum
Source ID: ord-8781cd360db7461e947183ea65b06389Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(tert-butoxycarbonyl)-2-(4-nitrophenoxy)ethylamine (5.91 g) was dissolved into methanol (200 ml) and subjected to hydrogeration reaction at ambient pressure by adding 10% palladium carbon catalyst (0.5 g). After completion of hydrogeration reaction, excess catalyst was removed by filtration. Filtrate was concentrated under vacuum to obtain N-(tert-butoxycarbonyl)-2-(4-aminophenoxy)ethylamine (5.07 g) as color-less oily substance. (1-3) N-(tert-butoxycarbonyl)-2-(4-aminophenoxy)ethylamine (1.00 g) was dissolved into pyridine (5 ml) and 2,6-dimethoxybenzoic acid chloride (0.87 g) was added into the solution. After being stirred for one hour, the reaction mixture was concentrated under vacuum and residue was dissolved into chloroform (30 ml). The solution was washed with 1N sodium hydroxide aqueous solution (30 ml) followed by saturated sodium chloride (30 ml). Solvent was distilled out and residue was purified by silica-gel column chromatography (ethyl acetate:hexane=1:1) to obtain 4′-[2-(tert-butoxycarbonylamino)ethoxy]-2,6-dimethoxybenzanilide (1.17 g) as white powder. was added into the solution the reaction mixture was concentrated under vacuum and residue was dissolved into chloroform (30 ml) The solution was washed with 1N sodium hydroxide aqueous solution (30 ml) Solvent was distilled out residue was purified by silica-gel column chromatography (ethyl acetate:hexane=1:1)
Source ID: ord-ad248fe92edc4be1b7de9b2b93d61357Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(tert-butoxycarbonyl)-2-(4-nitrophenoxy)ethylamine (5.91 g) was dissolved into methanol (200 ml) and subjected to hydrogeration reaction at ambient pressure by adding 10% palladium carbon catalyst (0.5 g). After completion of hydrogeration reaction, excess catalyst was removed by filtration. Filtrate was concentrated under vacuum to obtain N-(tert-butoxycarbonyl)-2-(4-aminophenoxy)ethylamine (5.07 g) as color-less oily substance. (1-3) N-(tert-butoxycarbonyl)-2-(4-aminophenoxy)ethylamine (1.00 g) was dissolved into pyridine (5 ml) and 2,6-dimethoxybenzoic acid chloride (0.87 g) was added into the solution. After being stirred for one hour, the reaction mixture was concentrated under vacuum and residue was dissolved into chloroform (30 ml). The solution was washed with 1N sodium hydroxide aqueous solution (30 ml) followed by saturated sodium chloride (30 ml). Solvent was distilled out and residue was purified by silica-gel column chromatography (ethyl acetate:hexane=1:1) to obtain 4′-[2-(tert-butoxycarbonylamino)ethoxy]-2,6-dimethoxybenzanilide (1.17 g) as white powder. subjected to hydrogeration reaction at ambient pressure After completion of hydrogeration reaction, excess catalyst was removed by filtration Filtrate was concentrated under vacuum
Source ID: ord-8781cd360db7461e947183ea65b06389Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 314 mg(1.246 mmole) of t-BOC amine from Example 216 in 10 mL of methylene chloride was added pyridine (147 mg, 1.869 mmol, 1.5 eq) followed by benzenesulfonyl chloride (242 mg, 1.370 mmol, 1.1 eq) at room temperature. The reaction mixture was stirred at room temperature overnight and then partitioned between water and chloroform. The organic layer was separated and washed with 1N hydrochloric acid, water and brine and then dried over anhydrous sodium sulfate. The solution was filtered, concentrated and the residue was purified by flash colunto chromatography (eluant 2:1 hexanes/ethyl acetate) to give 248 mg (51%) of the product: 1H NMR (200 MHz, CDCl3) δ8.01 (d, 1H, J=8Hz), 7.67 (d, 2H, J=8Hz), 6.92 (d, 2H, J=9Hz), 6.72 (s, 1H, N-H), 6.70 (d, 2H, J=9Hz), 4.90 (bs, 1H, N-H), 3.89 (t, 2H, J=5.0Hz), 3.40 (q, 2H, J=5.0Hz), 1.40 (s, 9H). partitioned between water and chloroform The organic layer was separated washed with 1N hydrochloric acid, water and brine dried over anhydrous sodium sulfate The solution was filtered concentrated the residue was purified by flash colunto chromatography (eluant 2:1 hexanes/ethyl acetate)
Source ID: ord-175853e260ec48a0adcd6f5eaec785bcConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 775 mg (2.75 mmol) of nitro compound from Example 215 in 20 mL of methanol with 10% palladium on carbon (150 mg) was introduced hydrogen via balloon at room temperature for 4 h. The catalyst was filtered off through Celite, and the filterate was concentrated under vacuum to give 690 mg of the title compound: 1H NMR (200 MHz, CDCl3) 8 6.69 (d, 2H, J=8Hz), 6.58 (d, 2H, J=8Hz), 4.94 (bs, 1H, N-H), 3.89 (bt, 2H, J=5.0Hz), 3.40 (q, 2H, J=5.0Hz), 1.40 (s, 9H). The catalyst was filtered off through Celite the filterate was concentrated under vacuum
Source ID: ord-5dd56f1efd214f57b83f8a9cedba556cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 775 mg (2.75 mmol) of nitro compound from Example 215 in 20 mL of methanol with 10% palladium on carbon (150 mg) was introduced hydrogen via balloon at room temperature for 4 h. The catalyst was filtered off through Celite, and the filterate was concentrated under vacuum to give 690 mg of the title compound: 1H NMR (200 MHz, CDCl3) 8 6.69 (d, 2H, J=8Hz), 6.58 (d, 2H, J=8Hz), 4.94 (bs, 1H, N-H), 3.89 (bt, 2H, J=5.0Hz), 3.40 (q, 2H, J=5.0Hz), 1.40 (s, 9H). The catalyst was filtered off through Celite the filterate was concentrated under vacuum
Source ID: ord-5dd56f1efd214f57b83f8a9cedba556cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(tert-butoxycarbonyl)-2-(4-nitrophenoxy)ethylamine (5.91 g) was dissolved into methanol (200 ml) and subjected to hydrogeration reaction at ambient pressure by adding 10% palladium carbon catalyst (0.5 g). After completion of hydrogeration reaction, excess catalyst was removed by filtration. Filtrate was concentrated under vacuum to obtain N-(tert-butoxycarbonyl)-2-(4-aminophenoxy)ethylamine (5.07 g) as color-less oily substance. (1-3) N-(tert-butoxycarbonyl)-2-(4-aminophenoxy)ethylamine (1.00 g) was dissolved into pyridine (5 ml) and 2,6-dimethoxybenzoic acid chloride (0.87 g) was added into the solution. After being stirred for one hour, the reaction mixture was concentrated under vacuum and residue was dissolved into chloroform (30 ml). The solution was washed with 1N sodium hydroxide aqueous solution (30 ml) followed by saturated sodium chloride (30 ml). Solvent was distilled out and residue was purified by silica-gel column chromatography (ethyl acetate:hexane=1:1) to obtain 4′-[2-(tert-butoxycarbonylamino)ethoxy]-2,6-dimethoxybenzanilide (1.17 g) as white powder. was added into the solution the reaction mixture was concentrated under vacuum and residue was dissolved into chloroform (30 ml) The solution was washed with 1N sodium hydroxide aqueous solution (30 ml) Solvent was distilled out residue was purified by silica-gel column chromatography (ethyl acetate:hexane=1:1)
Source ID: ord-ad248fe92edc4be1b7de9b2b93d61357Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: N-(tert-butoxycarbonyl)-2-(4-nitrophenoxy)ethylamine (5.91 g) was dissolved into methanol (200 ml) and subjected to hydrogeration reaction at ambient pressure by adding 10% palladium carbon catalyst (0.5 g). After completion of hydrogeration reaction, excess catalyst was removed by filtration. Filtrate was concentrated under vacuum to obtain N-(tert-butoxycarbonyl)-2-(4-aminophenoxy)ethylamine (5.07 g) as color-less oily substance. (1-3) N-(tert-butoxycarbonyl)-2-(4-aminophenoxy)ethylamine (1.00 g) was dissolved into pyridine (5 ml) and 2,6-dimethoxybenzoic acid chloride (0.87 g) was added into the solution. After being stirred for one hour, the reaction mixture was concentrated under vacuum and residue was dissolved into chloroform (30 ml). The solution was washed with 1N sodium hydroxide aqueous solution (30 ml) followed by saturated sodium chloride (30 ml). Solvent was distilled out and residue was purified by silica-gel column chromatography (ethyl acetate:hexane=1:1) to obtain 4′-[2-(tert-butoxycarbonylamino)ethoxy]-2,6-dimethoxybenzanilide (1.17 g) as white powder. subjected to hydrogeration reaction at ambient pressure After completion of hydrogeration reaction, excess catalyst was removed by filtration Filtrate was concentrated under vacuum
Source ID: ord-8781cd360db7461e947183ea65b06389PubChem References
These sources are listed in the compound's public database record.
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