Home Cart 0 Sign in  

[ CAS No. 99370-68-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 99370-68-0
Chemical Structure| 99370-68-0
Structure of 99370-68-0 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 99370-68-0 ]

Related Doc. of [ 99370-68-0 ]

Alternatived Products of [ 99370-68-0 ]

Product Details of [ 99370-68-0 ]

CAS No. :99370-68-0 MDL No. :MFCD02947280
Formula : C11H10O4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 206.20 Pubchem ID :-
Synonyms :

Safety of [ 99370-68-0 ]

Signal Word: Class:
Precautionary Statements: UN#:
Hazard Statements: Packing Group:

Application In Synthesis of [ 99370-68-0 ]

* 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.

  • Downstream synthetic route of [ 99370-68-0 ]

[ 99370-68-0 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 99370-68-0 ]
  • [ 135065-71-3 ]
  • [ 919286-66-1 ]
YieldReaction ConditionsOperation in experiment
40% With di-isopropyl azodicarboxylate; In tetrahydrofuran; for 22.1667h; Step d) (R)-2-(2-ethoxycarbonyl-benzofuran-5-yloxymethyl)-morpholine-4-carboxylic acid terf-butyl esterPS-triphenylphosphine resin (1.64g, 4.9mmol) was swelled in anhydrous THF (20ml). Diisopropyl azodicarboxylate (85OuI, 4.2mmol) was added slowly and the suspension agitated for 10min. (R)-2-hydroxymethyl-4-tert- butoxycarbonyl-morpholine (710mg, 3.3mmol) and 5-hydroxy-benzofuran-2- carboxylic acid ethyl ester (680mg, 3.3mmol) were then added and the reaction agitated for a further 18h. Reaction was filtered and to the filtrate was EPO <DP n="34"/>added more PS-triphenylphosphine resin (1.64g, 4.9mmol) and diisopropyl azodicarboxylate (85OuI, 4.2mmol). After a further 4h of agitation reaction was filtered again and concentrated in vacuo. Purification by prep-HPLC gave the desired product as white solid. (520mg, 40%), m/z = 406(M+H), 306(M+H - Boc) in MS ES+.
With triphenylphosphine on polystyrene; di-isopropyl azodicarboxylate; In dichloromethane; at 20℃; for 32h; 4-Boc-2R-hydroxymethylmorpholine was prepared according to method described in Heterocycles, 1993 35, 105-109. To a mixture of polymer supported triphenylphosphine (2.4 mmol) and the hydroxymethylmorpholine (1. 2 mmol) in dry dichloromethane (5 ml) ethyl-5-hydroxybenzofuran-2-carboxylate (1. 2 mmol) and DIAD (1.2 mmol) was added at room temperature. The mixture was stirred further 16 hours, fitrated, diluted in dry dichloromethane (5 ml) and stirred at room temperature another 16 hours. Filtrated, concentrated in vacuo and purified by y flash chromatography on silica (ethylacetate, hexane) to yield ethyl-5- (4-boc-morpholino-2R-methyloxy) benzofuran carboxylate (0.3 mmol), m/z = 406 in MS ES+, as an oil.
With di-isopropyl azodicarboxylate; In dichloromethane; at 20℃; for 16h; 4-Boc-2R-hydroxymethylmorpholine was prepared according to method described in Heterocycles, 1993 35, 105-109. To a mixture of polymer supported triphenylphosphine (2.4 mmol) and the hydroxymethylmorpholine ( 1.2 mmol) in dry dichloromethane (5 ml) ethyl-5-hydroxybenzofuran-2-carboxylate (1.2 mmol) and DIAD (1.2 mmol) was added at room temperature. The mixture was stirred further 16 hours, fitrated, diluted in dry dichloromethane (5 ml) and stirred at room temperature another 16 hours. Filtrated, concentrated in vacuo and purified by y flash chromatography on silica (ethylacetate, hexane)to yield ethyl-5-(4-boc-morpholino-2R-methyloxy)benzofuran carboxylate (0.3 mmol), m/z = 406 in MS ES+, as an oil.
  • 2
  • [ 212650-43-6 ]
  • [ 99370-68-0 ]
  • [ 920009-78-5 ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine on polystyrene; di-isopropyl azodicarboxylate; In dichloromethane; at 20℃; Ethyl 5-methoxybenzofuran carboxylate (22.7 mmol) was dissolved in dichloromethane (20 ml) and a 1.0 M solution of boron tribromide methyl sulphide complex in dichloromethane (68. 1 mmol) was added. The mixture was heated at reflux over night. The solvent was evaporated under vacuo and the residue purified by flash chromatography to obtain ethyl 5-hydroxybenzofuran carboxylate as a white solid. Triphenyl phosphine polymer bound (8.96 mmol) was suspended in anhydrous dichloromethane (20 ml) then diisopropyl azodicarboxylate (7.76 mmol) was added and the mixture was stirred for 15 minutes at room temperature. Then ethyl 5- hydroxybenzofuran carboxylate (5.97 mmol) was added over 5 minutes followed by the addition of 4-N-boc-3-morpholinecarboxylic acid (5.97 mmol) over 5 minutes too. The mixture was stirred at room temperature over night. The solvent was evaporated under vacuo and the residue purified by flash chromatography to obtain ethyl 5- (4-Boc- morpholin-2-ylmethoxy)-benzofuran-2-carboxylate : m/z = 406 in MS ES+, as clear oil. Ethyl 5- (4-Boc-morpholin-2-ylmethoxy)-benzofuran-2-carboxylate (2.47 mmol) was dissolved in 30 ml of a 4.0 M solution of hydrochloric acid in dioxan and stirred at room temperature for 1 hour. After removing the solvent under vacuo the resulting amine was dissolved in anhydrous dichloromethane and N-methylmorpholine (5.67 mmol) was added and stirred at room temperature for 5 minutes. Then allylchloroformate (2.71 mmol) was added and the mixture was stirred at room temperature over night under an inert atmosphere. The mixture was washed with a 1.0 M solution of hydrochloric acid, water, dried over Na2SO4 and the solvent was evaporated in vacuo. The residue was purified by flash chromatography to yield ethyl 5- (4-alloc-morpholin-2-ylmethoxy)- benzofuran-2-carboxylate : m/z = 390 in MS ES+, as a white solid. Ethyl 5- (4-alloc-morpholin-2-ylmethoxy)-benzofuran-2-carboxylate (2.09 mmol) was dissolved in 3 ml of tetrahydrofuran. Then 3 mi of a 1.0 M solution of lithium hydroxide were added and the mixture stirred at room temperature over night. After removing the tetrahydrofuran under vacuo the mixture was acidified with a 1 M solution of hydrochloric acid to Congo red, extracted with dichloromethane, washed with water, dried over Na2SO4 and the solvent was removed under vacuo to yield 5- (4-alloc- morpholin-2-ylmethoxy)-benzofuran-2-carboxylic acid as a white solid. 5- (4-Alloc-morpholin-2-ylmethoxy)-benzofuran-2-carboxylic acid (3 equiv) was then incorporated on the peptide as described previously (600 mg; 0.32 mmol/g) with HBTU (3 equiv), HOBt (3 equiv) and NMM (6 equiv) in DMF over night at room temperature. The Alloc group was removed with (1) DCM (4 x 1 min) ; (2) borane dimethylamine complex (40 equiv), tetrakis (triphenylphosphine) palladium (0) (0.1 equiv) in anhydrous DCM (2 x 15 min); (3) DCM (3 x 1 min) ; (4) DMF (3 x 1 min); (5) dioxan-water (9: 1) (3 x 1 min); (6) DMF (3 x 1 min); (7) MeOH (3 x 1 min); (8) DCM (3 x 1 min) and the peptide resin was treated with dibutyltin dichloride (5 equiv), phenylsilane (5 equiv) and a 37% solution of formaldehyde in water (5 equiv) in THF for 2 hours at room temperature. The reminder of the procedure was carried out as described in the general protocol.
  • 3
  • [ 56172-36-2 ]
  • [ 99370-68-0 ]
YieldReaction ConditionsOperation in experiment
In ethanol; (a) Ethyl 5-hydroxybenzofuran-2-carboxylate <strong>[56172-36-2]5-Hydroxybenzofuran-2-carboxylic acid</strong> (1.1 g) was heated under reflux for 1 hour in ethanol (50 ml) saturated with hydrogen chloride gas. The reaction mixture was cooled, poured into water and extracted with ethyl acetete, which was washed with water and dried over magnesiuym sulphate. The solvent was evaporated and the residue triturated with petroleum ether to give a brown powder, which was treated with ether, filtered from a black tar and the filtrate eluted down a silica gel column using ether as eluant to give 0.78 g of the sub-title ester as a colourless solid mp 110-112. Elemental analysis: Found: C 64.0 H 5.0%. C11 H10 O4 Required: C 64.1 H 4.85%.
  • 4
  • [ 99370-68-0 ]
  • [ 135065-76-8 ]
  • [ 919286-79-6 ]
YieldReaction ConditionsOperation in experiment
70% With di-isopropyl azodicarboxylate; In tetrahydrofuran; for 21.1667h; Step d) (S)-2-(2-ethoxycarbonyl-benzofuran-5-yloxymethyl)-morpholine- 4-carboxylic acid terf-butyl esterPS-triphenylphosphine resin (1.85g, 5.6mmol) was swelled in anhydrous THF (20ml). Diisopropyl azodicarboxylate (95OuI, 4.8mmol) was added slowly and the suspension agitated for 10min. (S)-2-hydroxymethyl-4-tert-butoxycarbonyl- morpholine (800mg, 3.7mmol) and 5-hydroxy-benzofuran-2-carboxylic acid ethyl ester (760mg, 3.7mmol) were then added and the reaction agitated for a further 18h. Reaction was filtered and to the filtrate was added more PS- triphenylphosphine resin (1.85g, 5.6mmol) and diisopropyl azodicarboxylate (95OuI, 4.8mmol). After a further 3h of agitation reaction was filtered again and concentrated in vacuo. Purification by prep-HPLC gave the desired product as white solid. (1.02g, 70%), m/z = 406(M+H), 306(M+H -Boc) in MS ES+.
  • 5
  • [ 5570-78-5 ]
  • [ 99370-68-0 ]
  • [ 1106537-39-6 ]
YieldReaction ConditionsOperation in experiment
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 10 - 20℃; for 3h; Step 4 5-(1-Isopropyl-piperidin-4-yloxy)-benzofuran-2-carboxylic acid ethyl ester The above prepared 5-hydroxy-benzofuran-2-carboxylic acid ethyl ester (1.50 g, 7.27 mmol) was dissolved in 36 mL of THF and treated successively at 10 C. with <strong>[5570-78-5]1-isopropyl-piperidin-4-ol</strong> (1.46 g, 1.4 eq.), triphenylphosphine (2.67 g, 1.4 eq.) and DIAD (2.00 mL, 1.4 eq.), and the mixture then kept at ambient temperature for another 3 h. Pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, NEt3/AcOEt=2/98), yielded finally 1.36 g of the title compound as light yellow oil. MS (ISP): 332.3 [M+H]+.
  • 6
  • [ 99370-68-0 ]
  • [ 135065-69-9 ]
  • [ 920009-78-5 ]
YieldReaction ConditionsOperation in experiment
Ethyl 5-methoxybenzofuran carboxylate (22.7 mmol) was dissolved in dichloromethane (20 ml) and a 1.0 M solution of boron tribromide methyl sulphide complex in dichloromethane (68.1 mmol) was added. The mixture was heated at reflux over night. The solvent was evaporated under vacuo and the residue purified by flash chromatography to obtain ethyl 5-hydroxybenzofuran carboxylate as a white solid. Triphenyl phosphine polymer bound (8.96 mmol) was suspended in anhydrous dichloromethane (20 ml) then diisopropyl azodicarboxylate (7.76 mmol) was added and the mixture was stirred for 15 minutes at room temperature. Then ethyl 5- hydroxybenzofuran carboxylate (5.97 mmol) was added over 5 minutes followed by the addition of 4-N-boc-3-morpholinecarboxylic acid (5.97 mmol) over 5 minutes too. The mixture was stirred at room temperature over night. The solvent was evaporated under vacuo and the residue purified by flash chromatography to obtain ethyl 5-(4-Boc- morpholin-2-ylmethoxy)-benzofuran-2-carboxylate: m/z = 406 in MS ES+, as clear oil. Ethyl 5-(4-Boomorpholin-2-ylmethoxy)-benzofuran-2-carboxylate (2.47 mmol) was dissolved in 30 ml of a 4.0 M solution of hydrochloric acid in dioxan and stirred at room temperature for 1 hour. After removing the solvent under vacuo the resulting amine was dissolved in anhydrous dichloromethane and N-methylmorpholine (5.67 mmol) was added and stirred at room temperature for 5 minutes. Then allylchloroformate (2.71 mmol) was added and the mixture was stirred at room temperature over night under an inert atmosphere. The mixture was washed with a 1.0 M solution of hydrochloric acid, water, dried over Na2SU4 and the solvent was evaporated in vacuo. The residue was purified by flash chromatography to yield ethyl 5-(4-alloc-morpholin-2-ylmethoxy)- benzofuran-2-carboxylate: m/z = 390 in MS ES+, as a white solid. Ethyl 5-(4-alloc-morpholin-2-ylmethoxy)-benzofuran-2-carboxylate (2.09 mmol) was dissolved in 3 ml of tetrahydrofuran. Then 3 ml of a 1.0 M solution of lithium hydroxide were added and the mixture stirred at room temperature over night. After removing the tetrahydrofuran under vacuo the mixture was acidified with a 1 M solution of hydrochloric acid to Congo red, extracted with dichloromethane, washed with water, dried over Na2SU4 and the solvent was removed under vacuo to yield 5-(4-alloc- morpholin-2-ylmethoxy)-benzofuran-2-carboxylic acid as a white solid. EPO <DP n="100"/>5-(4-Alloc-morpholin-2-ylmethoxy)-benzofuran-2-carboxylic acid (3 equiv) was then incorporated on the peptide as described previously (600 mg; 0.32 mmol/g) with HBTU (3 equiv), HOBt (3 equiv) and NMM (6 equiv) in DMF over night at room temperature. The Alloc group was removed with (1 ) DCM (4 x 1 min); (2) borane dimethylamine complex (40 equiv), tetrakis (triphenylphosphine) palladium (0) (0.1 equiv) in anhydrous DCM (2 x 15 min); (3) DCM (3 x 1 min); (4) DMF (3 x 1 min); (5) dioxan-water (9:1 ) (3 x 1 min); (6) DMF (3 x 1 min); (7) MeOH (3 x 1 min); (8) DCM (3 x 1 min) and the peptide resin was treated with dibutyltin dichloride (5 equiv), phenylsilane (5 equiv) and a 37% solution of formaldehyde in water (5 equiv) in THF for 2 hours at room temperature. The reminder of the procedure was carried out as described in the general protocol.
  • 7
  • [ 56979-56-7 ]
  • [ 99370-68-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 60 h / Reflux 2: hydrogen; palladium on activated charcoal / ethanol / 20 °C
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 60 h / Reflux 2: hydrogen; palladium on activated charcoal / ethanol / 20 °C
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethanol; ethyl acetate / 1 h / 20 °C
  • 8
  • [ 99370-68-0 ]
  • [ 158690-56-3 ]
  • ethyl 5-(2-((tert-butoxycarbonyl)amino)ethoxy)benzofuran-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; A mixture containing 2-((tert-butoxycarbonyl)amino)ethyl 4-methylbenzenesulfonate (306 mg, 0.96 mmol), potassium carbonate (268 mg, 1.94 mmol), and ethyl 5- hydroxybenzofuran-2-carboxylate (200 mg, 0.96 mmol) in N,N-dimethylformamide (2 mL) was stirred at 50C overnight. TLC showed the reaction was complete. The reaction mixture was worked up and the crude residue was purified by silica gel flash column chromatography (eluted with 30% ethyl acetate in hexane) to afford ethyl 5-(2-((tert- butoxycarbonyl)amino)ethoxy)benzofuran-2-carboxylate (200 mg, yield 59%) as a white solid. LC/MS (ES+): m/z 372.1 [M+Na]+. tR = 2.725 min.
Same Skeleton Products
Historical Records