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[ CAS No. 1029438-14-9 ]

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Chemical Structure| 1029438-14-9
Chemical Structure| 1029438-14-9
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Product Details of [ 1029438-14-9 ]

CAS No. :1029438-14-9 MDL No. :MFCD16295057
Formula : C14H13BO3 Boiling Point : 441.5±47.0°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :240.06 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1029438-14-9 ]

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:

Application In Synthesis of [ 1029438-14-9 ]

  • Downstream synthetic route of [ 1029438-14-9 ]

[ 1029438-14-9 ] Synthesis Path-Downstream   1~5

YieldReaction ConditionsOperation in experiment
47% With potassium carbonate In ethanol; water at 50℃; for 5h; Inert atmosphere; 60 General procedure: Under a nitrogen gas atmosphere, Phenylboronic acid150 mg (1.23 mmol)324 mg (0.55 mmol) of potassium salt of stable art type complex of 4-bromophenylboronic acid and scyllo-inositol (0.55 mmol) of potassium salt of scyllo-inositol and 340 mg (2.46 mmol) of potassium carbonate were dissolved in degassed ethanol: 1) mixed solvent, and a catalyst solution prepared by suspending 8 mg (0.012 mmol) of triphenylphosphine ligand-palladium in 1 mL of a mixed solvent of ethanol: water (5: 1) was added thereto , And the cross-coupling reaction was started by stirring at a reaction temperature of 50 ° C. After 5 hours of reaction, the reaction solvent was distilled off under reduced pressure to stop the reaction. 15 ml of water and 10 ml of ethyl acetate were added to the residue and dissolved / extracted, and the obtained suspension was filtered to remove the insoluble catalyst. Further, an ethyl acetate layer and an aqueous layer were separated, and the aqueous layer was further washed with a small amount of ethyl acetate. The aqueous layer was taken out and hydrochloric acid was added so that the pH became 2 to 3, the scyllo-inositol complex dissociated and the deprotection reaction progressed. The arylboronic acid was insolubilized with deprotection in an acidic aqueous solution. Thereto, 15 ml of ethyl acetate was added to extract the arylboronic acid, and the mixture was separated to obtain an ethyl acetate layer. The aqueous layer was again extracted with 10 ml of ethyl acetate, combined with the first ethyl acetate solution, dried with anhydrous Na 2 SO 4 and concentrated. The precipitated solid was purified by silica gel column chromatography to obtain 187 mg (0.95 mmol) of biphenyl 4-boronic acid (yield: 86%).
  • 2
  • [ 1029438-14-9 ]
  • [ 186817-91-4 ]
  • (4S,5R,6S)-3-(4'-acetyl-biphenyl-4-yl)-4-methyl-7-oxo-6-((1'R)-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl-ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% Stage #1: (4R,5R,6S)-4-methyl-3,7-dioxo-6-((1'R)-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl-ester With triethylamine In dichloromethane for 0.25h; Inert atmosphere; Stage #2: With trifluoromethylsulfonic anhydride In dichloromethane at -78℃; for 0.5h; Stage #3: 4'-acetyl-biphenyl boronic acid With potassium hydroxide In tetrahydrofuran; dichloromethane; water at 20℃; 3 In a 25 ml Schlenk flask fitted with a rubber septum, magnetic stirrer and a balloon filled with dry nitrogen at -78 °C to a solution of (4f?,5S,6S)-4-methyl- 3,7-dioxo-6-((1'R)-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]heptane-2- carboxylic acid 4-nitro-benzyl-ester (110 mg, 0.23 mmol) in dry dichloromethane (0.9 ml) was added triethylamine (32 pi, 0.23 mmol). After 15 min, trifluoromethanesulfonic anhydride (39 μΙ, 0.23 mmol) was added to the resulting orange-yellow solution. After 30 min at -78 °C, Pd(dba)2 (7 mg, 0.012 mmol, 5 mol%), a solution of 4'-acetyl-biphenyl boronic acid (48 mg, 0.20 mmol) in tetrahydrofuran (2.5 ml), and aqueous potassium hydroxide (130 μΙ, 0.7 mmol, 5.4 M) were added sequentially. The dry-ice/acetone bath was removed and the mixture was allowed to warm to ambient temperature. Upon reaction completion, the wine-red solution was diluted in toluene (170 ml), washed three times with portions (40 ml) of water and once with brine (40 ml) and dried over magnesium sulfate. After filtration, the solvent was removed in a vacuum rotary evaporator, leaving a brownish oil. The crude product was purified by silica gel column chromatography using toluene-ethyl acetate (19:1) yielding a yellow oil(23 mg, 18 %). IR-spectrum (ATR): 2957, 2876, 1773, 1724, 1681 , 1603, 1521 , 1496, 1457, 1415, 1376, 1346, 1264, 1228, 1190, 1148, 1053, 1004, 958, 818, 736 cm"1.
  • 3
  • [ 1029438-14-9 ]
  • (4S,5R,6S)-3-(4'-acetyl-biphenyl-4-yl)-6-((1'R)-hydroxyethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl-ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0.25 h / Inert atmosphere 1.2: 0.5 h / -78 °C 1.3: 20 °C 2.1: hydrogenchloride / water; tetrahydrofuran / 0.67 h / 20 °C / pH 2.3
  • 4
  • [ 1029438-14-9 ]
  • potassium (4S,5R,6S)-3-(4'-acetyl-biphenyl-4-yl)-6-((1'R)-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0.25 h / Inert atmosphere 1.2: 0.5 h / -78 °C 1.3: 20 °C 2.1: hydrogenchloride / water; tetrahydrofuran / 0.67 h / 20 °C / pH 2.3 3.1: hydrogen; potassium hydrogencarbonate / palladium 10% on activated carbon / water; tetrahydrofuran / 0.17 h / 0 °C
  • 5
  • [ 1029438-14-9 ]
  • [ 165817-82-3 ]
  • [ 1354627-15-8 ]
YieldReaction ConditionsOperation in experiment
23 mg With potassium hydroxide; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; dichloromethane; water at -78 - 20℃; Inert atmosphere; 3 (4S,5R,6S)-3-(4'-Acetyl-biphenyl-4-yl)-4-methyl-7-oxo-64(1'R)-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl-ester In a 25 ml Schlenk flask fitted with a rubber septum, magnetic stirrer and a balloon filled with dry nitrogen at -78° C. to a solution of (4R,5S,6S)-4-methyl-3,7-dioxo-6-((1'R)-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl-ester (110 mg, 0.23 mmol) in dry dichloromethane (0.9 ml) was added triethylamine (32 μl, 0.23 mmol). After 15 min, trifluoromethanesulfonic anhydride (39 μl, 0.23 mmol) was added to the resulting orange-yellow solution. After 30 min at -78° C., Pd(dba)2 (7 mg, 0.012 mmol, 5 mol %), a solution of 4'-acetyl-biphenyl boronic acid (48 mg, 0.20 mmol) in tetrahydrofuran (2.5 ml), and aqueous potassium hydroxide (130 μl, 0.7 mmol, 5.4 M) were added sequentially. The dry-ice/acetone bath was removed and the mixture was allowed to warm to ambient temperature. Upon reaction completion, the wine-red solution was diluted in toluene (170 ml), washed three times with portions (40 ml) of water and once with brine (40 ml) and dried over magnesium sulfate. After filtration, the solvent was removed in a vacuum rotary evaporator, leaving a brownish oil. The crude product was purified by silica gel column chromatography using toluene-ethyl acetate (19:1) yielding a yellow oil (23 mg, 18%). IR-spectrum (ATR): 2957, 2876, 1773, 1724, 1681, 1603, 1521, 1496, 1457, 1415, 1376, 1346, 1264, 1228, 1190, 1148, 1053, 1004, 958, 818, 736 cm-1.
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