No renderable structure data available
C1COC2C1C(CO2)OC(=O)ON3C(=O)CCC3=OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl (2,5-dioxopyrrolidin-1-yl) carbonate |
|---|---|
| IUPAC Name | — |
| CAS Number | 253265-98-4 |
| Database ID | 17981482 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl (2,5-dioxopyrrolidin-1-yl) carbonate (CAS 253265-98-4) 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 17981482
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-9f559b512e4e40008753fac88a74f079Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 1-benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl-ammonium chloride (4) (29.70 g, 72.90 mmol, 1 equiv), triethylamine (22.00 g, 220 mmol, 3 equiv) and carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo[2,3-b]furan-3-yl ester (19.80 g, 73.00 mmol, 1 equiv) in 120 mL of dichlomethane were stirred at ambient temperature. Due to the incompleteness of the reaction, carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo[2,3-b]furan-3-yl ester (5.00 g, 18.43 mmol) was added to the solution. The solution was stirred at room temperature for 24 h. The solution was washed twice with 300 mL of water and once with 300 mL of saturated NaHCO3 solution. The organic layer was dried on MgSO4, filtered, and evaporated to dryness to obtain the desired product as a white solid. (37.04 g, 70.34 mmol, 96.4%). LRMS (ES+): m/z 527 [M+H]+. was added to the solution The solution was washed twice with 300 mL of water and once with 300 mL of saturated NaHCO3 solution The organic layer was dried on MgSO4 filtered evaporated to dryness
Source ID: ord-6f08d6f4c62c4e168d2d0442c5aa0486Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 1-benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl-ammonium chloride (4) (29.70 g, 72.90 mmol, 1 equiv), triethylamine (22.00 g, 220 mmol, 3 equiv) and carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo[2,3-b]furan-3-yl ester (19.80 g, 73.00 mmol, 1 equiv) in 120 mL of dichlomethane were stirred at ambient temperature. Due to the incompleteness of the reaction, carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo[2,3-b]furan-3-yl ester (5.00 g, 18.43 mmol) was added to the solution. The solution was stirred at room temperature for 24 h. The solution was washed twice with 300 mL of water and once with 300 mL of saturated NaHCO3 solution. The organic layer was dried on MgSO4, filtered, and evaporated to dryness to obtain the desired product as a white solid. (37.04 g, 70.34 mmol, 96.4%). LRMS (ES+): m/z 527 [M+H]+. was added to the solution The solution was washed twice with 300 mL of water and once with 300 mL of saturated NaHCO3 solution The organic layer was dried on MgSO4 filtered evaporated to dryness
Source ID: ord-6f08d6f4c62c4e168d2d0442c5aa0486Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-9f559b512e4e40008753fac88a74f079Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-isobutyl-carbamic acid benzyl ester 16 (7.54 g, 15 mmol) and 35 ml of 4M HCl in dioxane were stirred 30 min under an argon atmosphere. The mixture was concentrated in vacuo, and co-evaporated twice with dichloromethane. The residue was dissolved in dichloromethane (50 ml) and N,N-diisopropylethylamine (6.1 ml, 35 mmol), and carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo[2,3-b]furan-3-yl ester 17 (4.88 g, 18 mmol) was added. The reaction mixture was stirred overnight, and then concentrated in vacuo. The residue was diluted with dichloromethane, and sequentially washed with brine, 10% KHSO4, brine, saturated NaHCO3, and brine, then dried over MgSO4, and concentrated in vacuo. The oily residue was purified by flash chromatography using 70:30 ethyl acetate hexane as eluant, to give [3-(Hexahydro-furo[2,3-b]furan-3-yloxycarbonylamino)-2-hydroxy-4-phenyl-butyl]-isobutyl-carbamic acid benzyl ester 18 (5.8 g, 73%) as a white solid. TLC: Rf 0.56 (7:3 ethyl acetate:hexane). MS 527 (MH)+. The mixture was concentrated in vacuo The residue was dissolved in dichloromethane (50 ml) concentrated in vacuo The residue was diluted with dichloromethane sequentially washed with brine, 10% KHSO4, brine, saturated NaHCO3, and brine dried over MgSO4 concentrated in vacuo The oily residue was purified by flash chromatography
Source ID: ord-310f25b674034757af00127b7b680791Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-isobutyl-carbamic acid benzyl ester 16 (7.54 g, 15 mmol) and 35 ml of 4M HCl in dioxane were stirred 30 min under an argon atmosphere. The mixture was concentrated in vacuo, and co-evaporated twice with dichloromethane. The residue was dissolved in dichloromethane (50 ml) and N,N-diisopropylethylamine (6.1 ml, 35 mmol), and carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo[2,3-b]furan-3-yl ester 17 (4.88 g, 18 mmol) was added. The reaction mixture was stirred overnight, and then concentrated in vacuo. The residue was diluted with dichloromethane, and sequentially washed with brine, 10% KHSO4, brine, saturated NaHCO3, and brine, then dried over MgSO4, and concentrated in vacuo. The oily residue was purified by flash chromatography using 70:30 ethyl acetate hexane as eluant, to give [3-(Hexahydro-furo[2,3-b]furan-3-yloxycarbonylamino)-2-hydroxy-4-phenyl-butyl]-isobutyl-carbamic acid benzyl ester 18 (5.8 g, 73%) as a white solid. TLC: Rf 0.56 (7:3 ethyl acetate:hexane). MS 527 (MH)+. The mixture was concentrated in vacuo The residue was dissolved in dichloromethane (50 ml) concentrated in vacuo The residue was diluted with dichloromethane sequentially washed with brine, 10% KHSO4, brine, saturated NaHCO3, and brine dried over MgSO4 concentrated in vacuo The oily residue was purified by flash chromatography
Source ID: ord-310f25b674034757af00127b7b680791Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-isobutyl-carbamic acid benzyl ester 16 (7.54 g, 15 mmol) and 35 ml of 4M HCl in dioxane were stirred 30 min under an argon atmosphere. The mixture was concentrated in vacuo, and co-evaporated twice with dichloromethane. The residue was dissolved in dichloromethane (50 ml) and N,N-diisopropylethylamine (6.1 ml, 35 mmol), and carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo[2,3-b]furan-3-yl ester 17 (4.88 g, 18 mmol) was added. The reaction mixture was stirred overnight, and then concentrated in vacuo. The residue was diluted with dichloromethane, and sequentially washed with brine, 10% KHSO4, brine, saturated NaHCO3, and brine, then dried over MgSO4, and concentrated in vacuo. The oily residue was purified by flash chromatography using 70:30 ethyl acetate hexane as eluant, to give [3-(Hexahydro-furo[2,3-b]furan-3-yloxycarbonylamino)-2-hydroxy-4-phenyl-butyl]-isobutyl-carbamic acid benzyl ester 18 (5.8 g, 73%) as a white solid. TLC: Rf 0.56 (7:3 ethyl acetate:hexane). MS 527 (MH)+. The mixture was concentrated in vacuo The residue was dissolved in dichloromethane (50 ml) concentrated in vacuo The residue was diluted with dichloromethane sequentially washed with brine, 10% KHSO4, brine, saturated NaHCO3, and brine dried over MgSO4 concentrated in vacuo The oily residue was purified by flash chromatography
Source ID: ord-310f25b674034757af00127b7b680791Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: {1-Benzyl-2-hydroxy-3-[isobutyl-(3-methyl-1H-indazole-5-sulfonyl)-amino]-propyl}-carbamic acid tert-butyl ester (25 mg, 0.047 mmol) was added to a solution of 4N HCl in dioxane (0.25 mL). Material precipitated out so 800 uL conc. HCl was added and the reaction heated at reflux for 2 h. The resulting solution was concentrated under vacuum and concentrated 2 additional times from 1 mL methylene chloride. This crude amine was dissolved in 0.5 mL methylene chloride and diisopropylethylamine (80 uL, 0.46 mmol) was then added. To this solution was added carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo[2,3-b]furan-3-yl ester (16 mg, 0.055 mmol) and the reaction stirred overnight. The reaction was concentrated under vacuum and purified by preparative HPLC. MS 587 (MH+). Material precipitated out so 800 uL conc. HCl was added the reaction heated at reflux for 2 h The resulting solution was concentrated under vacuum concentrated 2 additional times from 1 mL methylene chloride This crude amine was dissolved in 0.5 mL methylene chloride The reaction was concentrated under vacuum purified by preparative HPLC
Source ID: ord-ce026a901f9f47dc966a3a7150cbc0c2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-isobutyl-carbamic acid benzyl ester 16 (7.54 g, 15 mmol) and 35 ml of 4M HCl in dioxane were stirred 30 min under an argon atmosphere. The mixture was concentrated in vacuo, and co-evaporated twice with dichloromethane. The residue was dissolved in dichloromethane (50ml) and N,N-diisopropylethylamine (6.1 ml, 35 mmol), and carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo[2,3-b]furan-3-yl ester 17 (4.88g, 18 mmol) was added. The reaction mixture was stirred overnight, and then concentrated in vacuo. The residue was diluted with dichloromethane, and sequentially washed with brine, 10% KHSO4, brine, saturated NaHCO3, and brine, then dried over MgSO4, and concentrated in vacuo. The oily residue was purified by flash chromatography using 70:30 ethyl acetate hexane as eluant, to give [3-(Hexahydro-furo[2,3-b]furan-3-yloxycarbonylamino)-2-hydroxy-4-phenyl-butyl]-isobutyl-carbamic acid benzyl ester 18 (5.8 g, 73%) as a white solid. TLC: Rf 0.56 (7:3 ethyl acetate: hexane). MS 527 (MH)+. The mixture was concentrated in vacuo The residue was dissolved in dichloromethane (50ml) concentrated in vacuo The residue was diluted with dichloromethane sequentially washed with brine, 10% KHSO4, brine, saturated NaHCO3, and brine dried over MgSO4 concentrated in vacuo The oily residue was purified by flash chromatography
Source ID: ord-53d1f816a897459a8db0121cd6ac7f8eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 1-benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl-ammonium chloride (4) (29.70 g, 72.90 mmol, 1 equiv), triethylamine (22.00 g, 220 mmol, 3 equiv) and carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo-[2,3b]furan-3-yl ester (19.80 g, 73.00 mmol, 1 equiv) in 120 mL of dichlomethane were stirred at ambient temperature. Due to the incompleteness of the reaction, carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo[2,3-b]furan-3-yl ester (5.00 g, 18.43 mmol) was added to the solution. The solution was stirred at room temperature for 24 h. The solution was washed twice with 300 mL of water and once with 300 mL of saturated NaHCO3 solution. The organic layer was dried on MgSO4, filtered, and evaporated to dryness to obtain the desired product as a white solid. (37.04 g, 70.34 mmol, 96.4%). LRMS (ES+): m/z 527 [M+H]+. was added to the solution The solution was washed twice with 300 mL of water and once with 300 mL of saturated NaHCO3 solution The organic layer was dried on MgSO4 filtered evaporated to dryness
Source ID: ord-28f8573f0dcb44be88582a3079a14c44Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-isobutyl-carbamic acid benzyl ester 16 (7.54 g, 15 mmol) and 35 ml of 4M HCl in dioxane were stirred 30 min under an argon atmosphere. The mixture was concentrated in vacuo, and co-evaporated twice with dichloromethane. The residue was dissolved in dichloromethane (50ml) and N,N-diisopropylethylamine (6.1 ml, 35 mmol), and carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo[2,3-b]furan-3-yl ester 17 (4.88g, 18 mmol) was added. The reaction mixture was stirred overnight, and then concentrated in vacuo. The residue was diluted with dichloromethane, and sequentially washed with brine, 10% KHSO4, brine, saturated NaHCO3, and brine, then dried over MgSO4, and concentrated in vacuo. The oily residue was purified by flash chromatography using 70:30 ethyl acetate hexane as eluant, to give [3-(Hexahydro-furo[2,3-b]furan-3-yloxycarbonylamino)-2-hydroxy-4-phenyl-butyl]-isobutyl-carbamic acid benzyl ester 18 (5.8 g, 73%) as a white solid. TLC: Rf 0.56 (7:3 ethyl acetate: hexane). MS m/z 527 (MH)+. The mixture was concentrated in vacuo The residue was dissolved in dichloromethane (50ml) concentrated in vacuo The residue was diluted with dichloromethane sequentially washed with brine, 10% KHSO4, brine, saturated NaHCO3, and brine dried over MgSO4 concentrated in vacuo The oily residue was purified by flash chromatography
Source ID: ord-35af1aac3722480a9809e8be59c65349Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 1-benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl-ammonium chloride (4) (29.70 g, 72.90 mmol, 1 equiv), triethylamine (22.00 g, 220 mmol, 3 equiv) and carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo[2,3-b]furan-3-yl ester (19.80 g, 73.00 mmol, 1 equiv) in 120 mL of dichlomethane were stirred at ambient temperature. Due to the incompleteness of the reaction, carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo[2,3-b]furan-3-yl ester (5.00 g, 18.43 mmol) was added to the solution. The solution was stirred at room temperature for 24 h. The solution was washed twice with 300 mL of water and once with 300 mL of saturated NaHCO3 solution. The organic layer was dried on MgSO4, filtered, and evaporated to dryness to obtain the desired product as a white solid. (37.04 g, 70.34 mmol, 96.4%). LRMS (ES+): m/z 527 [M+H]+. was added to the solution The solution was washed twice with 300 mL of water and once with 300 mL of saturated NaHCO3 solution The organic layer was dried on MgSO4 filtered evaporated to dryness
Source ID: ord-6f08d6f4c62c4e168d2d0442c5aa0486PubChem References
These sources are listed in the compound's public database record.
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