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CAS No. : | 1355620-88-0 | MDL No. : | MFCD22573388 |
Formula : | C15H17NO5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 291.30 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
72% | Stage #1: 1-(3-amino-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-ethanone With sodium methylate In 1,2-dimethoxyethane for 0.5h; Stage #2: formic acid ethyl ester In 1,2-dimethoxyethane | 10.3 To a solution of l-(3-Amino-6,7,9,10,12,13-hexahydro-5,8,l 1,14-tetraoxa- benzocyclo- dodecen-2-yl)-ethanone (108mmol, 29.3g) in DME (700ml) was added sodium methoxide (432mmol, 23.35g). The mixture was stirred for 30 minutes. Ethyl formate (540mmol, 44ml) was added and the mixture was stirred overnight. (Additional sodium methoxide may be needed if reaction is not complete as monitored by LC/MS.) After the reaction was completion, the mixture was diluted with water (40ml) and acidified to neutral with 1M HCl . The precipitate was filtered and washed with water, dried in vacuo to afford 22g (72%) of 7,8,10,11,13,14 Hexahydro -lH-6,9,12,15-tetraoxa-l-aza-cyclododeca[b]naphthalen -4-one. 1H NMR (400MHz, DMSO) δ 8.58 (s, 1H), 7.52 (s, 1H), 7.22 (s, 1H), 7.12 (m, 1H), 4.35 (s, 4H), 3.87 (d, 4H), 3.62 (s, 4H). LC/MS Calcd for (M+H)+ 292.3, found 292.5. |
72% | Stage #1: 1-(3-amino-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-ethanone With sodium methylate In 1,2-dimethoxyethane for 0.5h; Stage #2: formic acid ethyl ester In 1,2-dimethoxyethane | 10.3 Step 3 7,8,10,11,13,14-Hexahydro-1H-6,9,12,15-tetraoxa-1-aza-cyclododeca[b]naphthalen-4-one Step 3 7,8,10,11,13,14-Hexahydro-1H-6,9,12,15-tetraoxa-1-aza-cyclododeca[b]naphthalen-4-one To a solution of 1-(3-Amino-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-ethanone (108 mmol, 29.3 g) in DME (700 ml) was added sodium methoxide (432 mmol, 23.35 g). The mixture was stirred for 30 minutes. Ethyl formate (540 mmol, 44 ml) was added and the mixture was stirred overnight. (Additional sodium methoxide may be needed if reaction is not complete as monitored by LC/MS.) After the reaction was completion, the mixture was diluted with water (40 ml) and acidified to neutral with 1M HCl. The precipitate was filtered and washed with water, dried in vacuo to afford 22 g (72%) of 7,8,10,11,13,14 Hexahydro-1H-6,9,12,15-tetraoxa-1-aza-cyclododeca[b]naphthalen-4-one. 1H NMR (400 MHz, DMSO) δ 8.58 (s, 1H), 7.52 (s, 1H), 7.22 (s, 1H), 7.12 (m, 1H), 4.35 (s, 4H), 3.87 (d, 4H), 3.62 (s, 4H). LC/MS Calcd for (M+H)+ 292.3, found 292.5. |
72% | With sodium methylate In 1,2-dimethoxyethane | 10.3 Step 3: 7,8,10,11,13,14-Hexahydro-1H-6,9,12,15-tetraoxa-1-aza-cyclododecane[B] naphthalen-4-one 1- (3-amino-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxy-benzocyclododecan-2-yl)(108 mmol, 29.3 g)DME solution (700 ml)Sodium methoxide (432 mmol, 23.35 g) was added.The resulting mixture was stirred for 30 minutes.Formic acid ethyl ester(540 mmol, 44 ml)The mixture was stirred overnight.(The reaction was monitored by LC / MS, and further addition of sodium methoxide was required if the reaction was not complete). After completion of the reaction, the mixture was washed with water (40 ml) and acidified to neutral with IM HCl. The precipitate was filtered, washed with water and dried in vacuo to give 22 g (72%) of 7,8,10,11,13,14-hexahydro-1H-6,9,12,15-tetraoxa-1- Alkyl [b] naphthalen-4-one. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With caesium carbonate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 2.5h; | 10.4 To a round bottom flask equipped with a magnetic stir bar was added 7,8,10,11,13,14- Hexahydro- lH-6,9, 12, 15-tetraoxa- 1 -aza-cyclododeca[b]naphthalen-4-one (12.2g, 43.3mmol, l .Oeq. ), acetonitrile (150ml), DMF (150ml) and cesium carbonate (28.2g, 86.5mmol, 2.0eq). The mixture was stirred at room temperature for 30 minutes at which time 1, 2-difluoro- 4-nitro-benzene (7.57g, 47.6mmoL, 1.1 eq) was added over a 10 minute period. After 2 hours the reaction was complete at which time 75% of the MeCN and DMF was removed and the resulting solution was poured over into ice water. The solid was filtered and dried and further columned with a biotage system. The eluent was 1 :3 ethyl acetate/hexane. Removal of the solvent afforded 4-(2-Fluoro-4-nitro-phenoxy)-7,8, 10,11,13,14-hexahydro-6,9, 12, 15-tetraoxa- l-aza-cyclodo-deca[b]naphthalene as a pale green solid (7.4g, 41% yield). ^-NMR (400MHz, DMSO): 8.58 (s, 1H), 7.80 (s, 1H), 7.50 (s, 1H), 7.04 (t, 1H), 6.88 (m, 1H), 6.50 (m, 2H), 4.35 (s, 4H), 3.87 (d, 4H), 3.62 (s, 4H). LC/MS Calcd for (M+H)+ 431.4, found 431.5. |
41% | With caesium carbonate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 2.66667h; | 10.4 Step 4 4-(2-Fluoro-4-nitro-phenoxy)-7,8,10,11,13,14-hexahydro-6,9,12,15-tetraoxa-1-aza-cyclododeca[b]naphthalene Step 4 4-(2-Fluoro-4-nitro-phenoxy)-7,8,10,11,13,14-hexahydro-6,9,12,15-tetraoxa-1-aza-cyclododeca[b]naphthalene To a round bottom flask equipped with a magnetic stir bar was added 7,8,10,11,13,14-Hexahydro-1H-6,9,12,15-tetraoxa-1-aza-cyclododeca[b]naphthalen-4-one (12.2 g, 43.3 mmol, 1.0 eq.), acetonitrile (150 ml), DMF (150 ml) and cesium carbonate (28.2 g, 86.5 mmol, 2.0 eq). The mixture was stirred at room temperature for 30 minutes at which time 1,2-difluoro-4-nitro-benzene (7.57 g, 47.6 mmoL, 1.1 eq) was added over a 10 minute period. After 2 hours the reaction was complete at which time 75% of the MeCN and DMF was removed and the resulting solution was poured over into ice water. The solid was filtered and dried and further columned with a biotage system. The eluent was 1:3 ethyl acetate/hexane. Removal of the solvent afforded 4-(2-Fluoro-4-nitro-phenoxy)-7,8,10,11,13,14-hexahydro-6,9,12,15-tetraoxa-1-aza-cyclodo-deca[b]naphthalene as a pale green solid (7.4 g, 41% yield). 1H-NMR (400 MHz, DMSO): 8.58 (s, 1H), 7.80 (s, 1H), 7.50 (s, 1H), 7.04 (t, 1H), 6.88 (m, 1H), 6.50 (m, 2H), 4.35 (s, 4H), 3.87 (d, 4H), 3.62 (s, 4H). LC/MS Calcd for (M+H)+ 431.4, found 431.5. |
41% | Stage #1: 7,8,10,11,13,14-hexahydro-1H-6,9,12,15-tetraoxa-1-aza-cyclododeca[b]naphthalen-4-one With caesium carbonate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.5h; Stage #2: 3,4-difluoronitrobenzene In N,N-dimethyl-formamide; acetonitrile for 2h; | 10.4 Step 4: 4- (2-Fluoro-4-nitro-phenoxy) -7,8,10,11,13,14-hexahydro-6,9,12,15-tetraoxy- -cyclododecane [b] naphthalene A round bottom flask equipped with a magnetic stirrer was charged7,8,10,11,13,14-hexahydro-1H-6,9,12,15-tetraoxo-1-aza-cyclododecane [b](12.2 g, 43.3 mmol, 1.0 eq),Acetonitrile (150 ml),DMF (150 ml) and cesium carbonate (28.2 g, 86.5 mmol, 2.0 eq).The resulting mixture was stirred at room temperature for 30 minutes,then,With 10 minutes,1,2-Fluoro-4-nitro-benzene (7.57 g, 47.6 mmol, 1.1 eq) was added.After 2 hours, the reaction was 75% complete,The acetonitrile and DMF were removed and then poured into ice water.The solid was filtered, dried, and passed through a column (available from Biotage). The eluent was 1: 3 ethyl acetate / n-hexane. Removal of the solvent gave 4- (2-fluoro-4-nitro-phenoxy) -7,8,10,11,13,14-hexahydro-6,9,12,15-tetraoxy- 1-aza-cyclododecane [b] naphthalene (7.4 g, yield 41%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: nitric acid; sulfuric acid / dichloromethane / 1.33 h / 0 °C 2: ammonium acetate; iron / toluene; water / Reflux 3: sodium methylate / 1,2-dimethoxyethane / 0.5 h | ||
Multi-step reaction with 3 steps 1.1: nitric acid / dichloromethane / 0 °C 1.2: 0.67 h / 0 °C 2.1: iron; ammonium acetate / toluene; water / Reflux 3.1: sodium methylate / 1,2-dimethoxyethane / 0.5 h | ||
Multi-step reaction with 3 steps 1.1: dichloromethane / 0.33 h / 0 °C 1.2: 1 h / 0 °C 2.1: iron; ammonium acetate / toluene; water / Reflux 3.1: sodium methylate / 1,2-dimethoxyethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ammonium acetate; iron / toluene; water / Reflux 2: sodium methylate / 1,2-dimethoxyethane / 0.5 h | ||
Multi-step reaction with 2 steps 1: iron; ammonium acetate / toluene; water / Reflux 2: sodium methylate / 1,2-dimethoxyethane / 0.5 h | ||
Multi-step reaction with 2 steps 1: iron; ammonium acetate / toluene; water / Reflux 2: sodium methylate / 1,2-dimethoxyethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide; acetonitrile / 2.5 h / 20 °C 2: triethylamine; hydrogen / Pd/C / ethyl acetate; N,N-dimethyl-formamide; methanol / 1810.07 Torr | ||
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide; acetonitrile / 2.67 h / 20 °C 2: triethylamine; hydrogen; Pd/C / N,N-dimethyl-formamide; methanol / 1810.07 Torr | ||
Multi-step reaction with 2 steps 1.1: caesium carbonate / N,N-dimethyl-formamide; acetonitrile / 0.5 h / 20 °C 1.2: 2 h 2.1: triethylamine; Pd/C; hydrogen / N,N-dimethyl-formamide; ethyl acetate; methanol / 1810.07 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide; acetonitrile / 2.5 h / 20 °C 2: triethylamine; hydrogen / Pd/C / ethyl acetate; N,N-dimethyl-formamide; methanol / 1810.07 Torr 3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere; Cooling with ice | ||
Multi-step reaction with 3 steps 1.1: caesium carbonate / N,N-dimethyl-formamide; acetonitrile / 2.67 h / 20 °C 2.1: triethylamine; hydrogen; Pd/C / N,N-dimethyl-formamide; methanol / 1810.07 Torr 3.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.08 h / Inert atmosphere; Cooling with ice 3.2: 3 h / 20 °C | ||
Multi-step reaction with 3 steps 1.1: caesium carbonate / N,N-dimethyl-formamide; acetonitrile / 0.5 h / 20 °C 1.2: 2 h 2.1: triethylamine; Pd/C; hydrogen / N,N-dimethyl-formamide; ethyl acetate; methanol / 1810.07 Torr 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.08 h / Inert atmosphere; Cooling with ice 3.2: 3 h / 20 °C / Inert atmosphere |