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CAS No. : | 16841-19-3 | MDL No. : | MFCD00045414 |
Formula : | C6H10O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JJABOWZNFOCHMN-UHFFFAOYSA-N |
M.W : | 130.14 | Pubchem ID : | 117177 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.83 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 31.81 |
TPSA : | 57.53 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.95 cm/s |
Log Po/w (iLOGP) : | 0.99 |
Log Po/w (XLOGP3) : | 0.2 |
Log Po/w (WLOGP) : | 0.38 |
Log Po/w (MLOGP) : | 0.0 |
Log Po/w (SILICOS-IT) : | 0.55 |
Consensus Log Po/w : | 0.42 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -0.71 |
Solubility : | 25.6 mg/ml ; 0.196 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.97 |
Solubility : | 14.0 mg/ml ; 0.108 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.02 |
Solubility : | 125.0 mg/ml ; 0.959 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.45 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H317-H319 | 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 |
---|---|---|
95% | at 20℃; for 72 h; | To a solution of 1-hydroxycyclopentanecarboxylic acid (0.98 g, 7.5 mmol) in ethanol (3.8 ml) was added a cat amount of sulfuric acid. The reaction mixture was stuffed for 3 d at room temperature. The solvent was concentrated in vacuo. The residue was partitioned between ethyl acetate (75-ml) and brine (25-ml). The layers were separated. The aqueous layer wasextracted with one 75-ml portion of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (1.13 g, 95percent) as light brown oil. MS mle: 159 ([M+H]j |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sulfuric acid; at 20℃; for 72h; | To a solution of 1-hydroxycyclopentanecarboxylic acid (0.98 g, 7.5 mmol) in ethanol (3.8 ml) was added a cat amount of sulfuric acid. The reaction mixture was stuffed for 3 d at room temperature. The solvent was concentrated in vacuo. The residue was partitioned between ethyl acetate (75-ml) and brine (25-ml). The layers were separated. The aqueous layer wasextracted with one 75-ml portion of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (1.13 g, 95%) as light brown oil. MS mle: 159 ([M+H]j |
90% | With sulfuric acid; | Adding hydroxycyclopentanecarboxylic acid, ethanol, at a certain temperature slowly dropping concentrated sulfuric acid, after a period of time,Distillation distillation of ethanol,High vacuum distillationEthyl hydroxycyclopentylThe Yield 90%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With hydrogenchloride; acetic acid; for 10h; | Cyclopentanenitrile, hydrochloric acid, glacial acetic acid, and the reaction was carried out for 10 hours. After the completion of the reaction, most of the acid was distilled off,The base is neutralized to neutral and the water is distilled off under reduced pressure to give hydroxycyclopentanecarboxylic acid. Yield 80%. |
4.1 g | With hydrogenchloride; water; In acetic acid; for 3h;Reflux; | [00199] A solution of sodium metabisulfate (4.84 g, 0.025 mol) in distilled water (20 mL) was added over 45 mm to a stilTed mixture of cyclopentanone 1 (3.45 g, 0.04 1 mol), potassium cyanide (3.3 g, 0.05 1 mol), and water (20 mL). The mixture was stilTed at 25 C for 6 hrs. The mixture was extracted with ethyl acetate (2 x 100 mL) and the organics dried (Mg504), and concentrated to give 3.6 g of x-hydroxycyclopentanecarbonitrile as an oil.oil was dissolved in acetic acid (12.5 mL) and the solution was diluted with concentrated(37.5 mL). The solution was refluxed for 3 hrs and concentrated to an oily residue that was partitioned between water (50 mL) and EtOAc (50 mL). The organic phase was separated, dried (Mg504), and concentrated to an oily residue which solidified on standing to give 4.1of x-hydroxycyclopentanecarboxylic acid. This material was dissolved in MeOH (50 mL) and treated with concentrated sulfuric acid (1 drop). The solution was refluxed for 12 hrsconcentrated to an oily residue which was dissolved in EtOAc (50 mL) and washed with a 5% solution of sodium bicarbonate (50 mL). The organics were dried (Mg504), filtered, concentrated, and chromatographed on silica gel (80% Hexanes 20% EtOAc) to give ohydroxycyclopentanecarboxylic acid methyl ester 2 (3.66 g) as an clear colorless oil.. |
4.1 g | With hydrogenchloride; water; acetic acid; for 3h;Reflux; | A solution of sodium metabisulfate (4.84 g, 0.025 mol) in distilled water (20 mL) was added over 45 min to a stirred mixture of cyclopentanone 1 (3.45 g, 0.041 mol), potassium cyanide (3.3 g, 0.051 mol), and water (20 mL). The mixture was stirred at 25 C. for 6 hrs. The mixture was extracted with ethyl acetate (2×100 mL) and the organics dried (MgSO4), and concentrated to give 3.6 g of alpha-hydroxycyclopentanecarbonitrile as an oil. The oil was dissolved in acetic acid (12.5 mL) and the solution was diluted with concentrated HCl (37.5 mL). The solution was refluxed for 3 hrs and concentrated to an oily residue that was partitioned between water (50 mL) and EtOAc (50 mL). The organic phase was separated, dried (MgSO4), and concentrated to an oily residue which solidified on standing to give 4.1 g of alpha-hydroxycyclopentanecarboxylic acid. This material was dissolved in MeOH (50 mL) and treated with concentrated sulfuric acid (1 drop). The solution was refluxed for 12 hrs and concentrated to an oily residue which was dissolved in EtOAc (50 mL) and washed with a 5% solution of sodium bicarbonate (50 mL). The organics were dried (MgSO4), filtered, concentrated, and chromatographed on silica gel (80% Hexanes/20% EtOAc) to give alpha-hydroxycyclopentanecarboxylic acid methyl ester 2 (3.66 g) as an clear colorless oil. |
With hydrogenchloride; water; for 16h;Heating / reflux; | EXAMPLE l; N-({5-[5-chloro-3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)phenyl]-3-fluoropyridin-2-yl}methyl)-l-hydroxycyclopentanecarboxamide; A mixture of cyclopentanone (20.0 g, 237.8 mmol), potassium cyanide (18.6 g, 285.3 mmol) and 34 mL of deionized water was stirred vigorously. In a separate flask, sodium bisulfite (29.7 g, 285.3 mmol) was dissolved in 36 mL of deionized water. An addition funnel was attached to the reaction flask and then filled with the sodium bisulfite solution. To the stirring reaction mixture was added the sodium bisulfite solution, dropwise over 15 minutes. The reaction mixture was allowed to stir vigorously for 16 hours. The biphasic reaction mixture was partitioned between the water and EtOAc. The aqueous EPO <DP n="25"/>layer was extracted three times with EtOAc. The combined organic layers were dried over sodium sulfate, filtered and concentrated to provide 1-hydroxycyclopentanecarbonitrile.The 1-hydroxycyclopentanecarbonitrile (29.9 g, 268.8 mmol) was heated to reflux in 56 mL of concentrated hydrochloric acid for 16 hours. The volume of concentrated hydrochloric acid was reduced in vacuo and the resulting residue was taken up in chloroform. The resulting slurry was filtered and washed with additional chloroform. The organic washings were combined, dried over sodium sulfate and concentrated to yield 1-hydroxycyclopentanecarboxylic acid.A mixture of potassium acetate (3.10 g, 31.6 mmol), tert-buty [(5-bromo-3-fluoro- pyridin-2-yl)methyl]carbamate (3.21 g, 10.5 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-l,3,2- dioxaborolane (2.94 g, 11.6 mmol) in a sealed tube reaction vessel capped with a rubber septum was dissolved in 10 mL of DMSO. This heterogeneous mixture was then evacuated and purged with nitrogen three times prior to introduction of [l,r-bis(diphenylphosphino)ferrocene]dichloro-palladium(II), complex with DCM (1:1) (0.385 g, 0.530 mmol). The heterogeneous mixture was then evacuated and purged with nitrogen twice before the septum was replaced with a teflon screw-top cap. This sealed vessel was then heated to 90 0C for 2 hours. After cooling to ambient temperature, potassium carbonate (2.91 g5 21.1 mmol), water (10.5 mL), 5-(2-bromo-4-chloro-6-fluorophenyl)-2-methyl-2H-tetrazole (3.38 g, 11.6 mmol) and additional palladium catalyst (0.385 g, 0.530 mmol) were added and the reaction was sealed again. After heating to 80 C for 1 hour, the reaction was cooled, quenched with water, and partitioned between EtOAc and water. The mixture was filtered through a plug of celite with EtOAc. The aqueous layer was extracted once with EtOAc. The combined organic layers were washed with additional water and then brine prior to drying over sodium sulfate. Filtration and solvent removal provided material which was subjected to chromatography on silica gel eluting with 0-15% EtOAc in hexanes to yield tert-hvcy ({5-[5-chloro-3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)phenyl]-3-fluoropyridin- 2-yl}methyl)carbamate. The above carbamate was dissolved in 50 mL of dry EtOAc. Anhydrous HCl gas was then bubbled through the solution for 3 minutes. The reaction was stirred vigorously for one hour. The reaction mixture was slowly neutralized with a saturated aqueous sodium bicarbonate solution. The mixture was partitioned between water and EtOAc. The organic layer was washed with water and brine prior to drying over sodium sulfate. The extracts were filtered, concentrated, and purified by chromatography on silica gel eluting with 0-20% MeOH in dichloromethane to provide ({5-[5-chloro-3- fluoro-2-(2-methyl-2Eta-tetrazol-5-yl)phenyl]-3-fluoropyridin-2-yl}methyl)amine.To a mixture of the above fluoropyridinium compound (1.02 g, 2.48 mmol), 1-hydroxy- cyclopentanecarboxylic acid (0.485 g, 3.72 mmol), (IH- 1,2,3 -benzotriazol-1 -yloxy)[tris(dimethyl- amino)]phosphonium hexafluorophosphate (1.76 g, 3.97 mmol) in anhydrous dichloromethane (16 mL) EPO <DP n="26"/>was added triethylamine (0.754 g, 7.45 mmol). The reaction mixture was allowed to stir at ambient temperature for 1 hour. After the reaction was judged complete by LC/MS analysis, the volume of the reaction is reduced in vacuo. The residue was taken up in EtOAc, and the organic phase was successively washed with water, 0.25 NHCl and saturated sodium bicarbonate solution. The combined extracts were dried over sodium sulfate, filtered, and concentrated. The crude material was subjected to chromatography on silica gel eluting with 0-50% EtOAc in hexanes to yield the title compound as a white solid, which gave a proton NuMR spectrum consistent with theory and a mass ion (ES+) of 449.2 for M+H+: 1H NuMR (500 MHz, CDCI3) delta 8.13 (s, IH), 7.87 (bs, NH), 7.34 (d, J= 8.8 Hz, IH), 7.26 (m,2H), 4.65 (d, J= 4.8 Hz, 2H), 4.35 (s, 3H), 2.23-2.21 (m, 3H), 1.85-1.84 (m, 4H), 1.77-1.74 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sulfuric acid; at 65℃; for 2h; | A solution of <strong>[16841-19-3]1-<strong>[16841-19-3]hydroxycyclopentanecarboxylic acid</strong></strong> (1.4 g, 10.76 mmol) in MeOH (10 mL) was treated with conc. H2SO4 (1 drop), heated at 65 C. for 2 h, cooled to RT and concentrated to dryness. The residue was treated with satd. NaHCO3, extracted with DCM (3*) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford methyl 1-hydroxycyclopentanecarboxylate (1.45 g, 92%). 1H NMR (400 MHz, CDCl3): delta 3.79 (s, 3H), 2.92 (br s, 1H), 2.11-2.00 (m, 2H), 1.91-1.83 (m, 2H), 1.82-1.72 (m, 4H). |
92% | With sulfuric acid; at 65℃; for 2h; | A solution of <strong>[16841-19-3]1-<strong>[16841-19-3]hydroxycyclopentanecarboxylic acid</strong></strong> (1.4 g, 10.76 mmol) in MeOH (10 mL) was treated with cone. H2SO4 (1 drop), heated at 65 C. for 2 h, cooled to RT and concentrated to dryness. The residue was treated with satd. NaHCO3, extracted with DCM (3×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford methyl 1-hydroxycyclopentanecarboxylate (1.45 g, 92%). 1H NMR (400 MHz, CDCl3): delta 3.79 (s, 3H), 2.92 (br s, 1H), 2.11-2.00 (m, 2H), 1.91-1.83 (m, 2H), 1.82-1.72 (m, 4H). |
sulfuric acid; at 20℃; for 18h; | To a solution of <strong>[16841-19-3]1-<strong>[16841-19-3]hydroxycyclopentanecarboxylic acid</strong></strong> (2.00 g) in methanol (15 mL) was added cone, sulfuric acid (0.1 mL), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo, and the resultant residue was diluted with diethylether. The mixture was washed successively with an aqueous saturated sodium hydrogencarbonate solution and brine. The organic layer was dried over sodium sulfate and concentrated in vacuo to give methyl 1- hydroxy- cyclopentanecarboxylate (2.06 g) as a pale brown oil. MS(APCI) m/z: 162 [MH-NHU]+ |
3.66 g | With sulfuric acid; for 12h;Reflux; | [00199] A solution of sodium metabisulfate (4.84 g, 0.025 mol) in distilled water (20 mL) was added over 45 mm to a stilTed mixture of cyclopentanone 1 (3.45 g, 0.04 1 mol), potassium cyanide (3.3 g, 0.05 1 mol), and water (20 mL). The mixture was stilTed at 25 C for 6 hrs. The mixture was extracted with ethyl acetate (2 x 100 mL) and the organics dried (Mg504), and concentrated to give 3.6 g of x-hydroxycyclopentanecarbonitrile as an oil. The oil was dissolved in acetic acid (12.5 mL) and the solution was diluted with concentrated HC1 (37.5 mL). The solution was refluxed for 3 hrs and concentrated to an oily residue that was partitioned between water (50 mL) and EtOAc (50 mL). The organic phase was separated, dried (Mg504), and concentrated to an oily residue which solidified on standing to give 4.1 g of x-<strong>[16841-19-3]hydroxycyclopentanecarboxylic acid</strong>. This material was dissolved in MeOH (50 mL) and treated with concentrated sulfuric acid (1 drop). The solution was refluxed for 12 hrs and concentrated to an oily residue which was dissolved in EtOAc (50 mL) and washed with a 5% solution of sodium bicarbonate (50 mL). The organics were dried (Mg504), filtered, concentrated, and chromatographed on silica gel (80% Hexanes 20% EtOAc) to give o<strong>[16841-19-3]hydroxycyclopentanecarboxylic acid</strong> methyl ester 2 (3.66 g) as an clear colorless oil.. |
3.66 g | With sulfuric acid; for 12h;Reflux; | A solution of sodium metabisulfate (4.84 g, 0.025 mol) in distilled water (20 mL) was added over 45 min to a stirred mixture of cyclopentanone 1 (3.45 g, 0.041 mol), potassium cyanide (3.3 g, 0.051 mol), and water (20 mL). The mixture was stirred at 25 C. for 6 hrs. The mixture was extracted with ethyl acetate (2×100 mL) and the organics dried (MgSO4), and concentrated to give 3.6 g of alpha-hydroxycyclopentanecarbonitrile as an oil. The oil was dissolved in acetic acid (12.5 mL) and the solution was diluted with concentrated HCl (37.5 mL). The solution was refluxed for 3 hrs and concentrated to an oily residue that was partitioned between water (50 mL) and EtOAc (50 mL). The organic phase was separated, dried (MgSO4), and concentrated to an oily residue which solidified on standing to give 4.1 g of alpha-<strong>[16841-19-3]hydroxycyclopentanecarboxylic acid</strong>. This material was dissolved in MeOH (50 mL) and treated with concentrated sulfuric acid (1 drop). The solution was refluxed for 12 hrs and concentrated to an oily residue which was dissolved in EtOAc (50 mL) and washed with a 5% solution of sodium bicarbonate (50 mL). The organics were dried (MgSO4), filtered, concentrated, and chromatographed on silica gel (80% Hexanes/20% EtOAc) to give alpha-<strong>[16841-19-3]hydroxycyclopentanecarboxylic acid</strong> methyl ester 2 (3.66 g) as an clear colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With thionyl chloride; In ISOPROPYLAMIDE; | EXAMPLE 27 N-[4-(Phenylsulfonyl)phenyl]-1-hydroxy-cyclopentanecarboxamide A solution of <strong>[16841-19-3]1-<strong>[16841-19-3]hydroxycyclopentanecarboxylic acid</strong></strong> (0.76 g, 6.4 mmol) in dry dimethylacetamide (15 ml) was stirred under a nitrogen atmosphere at -10 C. Thionyl chloride (0.76 g, 6.4 mmol) was added and the resulting mixture was allowed to stir at -10 C. for 1 hour. 4-Phenylsulfonylaniline (1.0 g, 4.29 mmol) was then added and the reaction mixture was stirred at -10 C. for a further 15 mins. The solution was then allowed to warm to room temperature where it was stirred overnight. The reaction mixture was poured onto water, extracted with ethyl acetate, and the combined ethyl acetate portions were washed with water, and brine. After drying (Na2 SO4) the ethyl acetate was removed by evaporation. Crystallization from ethyl acetate/hexane yielded the title tertiary carbinol (0.70 g, 47%) as a white solid; mp=214.0-216.0 C. 1 H--NMR (300 MHz, d6 --DMSO): 1.73 (m, 6 H, CH2), 1.97 (m, 2H, CH2), 5.67 (s, 1H, OH), 7.64 (m, 3H, ArH), 7.94 (m, 6H, ArH), 10.13 (s, 1H, NH). MS (CI, CH4): 346(M+1, 100). Analysis for C18 H19 NO4 S: Calculated: C, 62.59; H, 5.54; N, 4.06. Found: C, 62.67; H, 5.58; N, 4.00. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In dichloromethane; at 20℃; for 1h; | EXAMPLE l; N-({5-[5-chloro-3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)phenyl]-3-fluoropyridin-2-yl}methyl)-l-hydroxycyclopentanecarboxamide; A mixture of cyclopentanone (20.0 g, 237.8 mmol), potassium cyanide (18.6 g, 285.3 mmol) and 34 mL of deionized water was stirred vigorously. In a separate flask, sodium bisulfite (29.7 g, 285.3 mmol) was dissolved in 36 mL of deionized water. An addition funnel was attached to the reaction flask and then filled with the sodium bisulfite solution. To the stirring reaction mixture was added the sodium bisulfite solution, dropwise over 15 minutes. The reaction mixture was allowed to stir vigorously for 16 hours. The biphasic reaction mixture was partitioned between the water and EtOAc. The aqueous EPO <DP n="25"/>layer was extracted three times with EtOAc. The combined organic layers were dried over sodium sulfate, filtered and concentrated to provide 1-hydroxycyclopentanecarbonitrile.The 1-hydroxycyclopentanecarbonitrile (29.9 g, 268.8 mmol) was heated to reflux in 56 mL of concentrated hydrochloric acid for 16 hours. The volume of concentrated hydrochloric acid was reduced in vacuo and the resulting residue was taken up in chloroform. The resulting slurry was filtered and washed with additional chloroform. The organic washings were combined, dried over sodium sulfate and concentrated to yield <strong>[16841-19-3]1-<strong>[16841-19-3]hydroxycyclopentanecarboxylic acid</strong></strong>.A mixture of potassium acetate (3.10 g, 31.6 mmol), tert-buty [(5-bromo-3-fluoro- pyridin-2-yl)methyl]carbamate (3.21 g, 10.5 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-l,3,2- dioxaborolane (2.94 g, 11.6 mmol) in a sealed tube reaction vessel capped with a rubber septum was dissolved in 10 mL of DMSO. This heterogeneous mixture was then evacuated and purged with nitrogen three times prior to introduction of [l,r-bis(diphenylphosphino)ferrocene]dichloro-palladium(II), complex with DCM (1:1) (0.385 g, 0.530 mmol). The heterogeneous mixture was then evacuated and purged with nitrogen twice before the septum was replaced with a teflon screw-top cap. This sealed vessel was then heated to 90 0C for 2 hours. After cooling to ambient temperature, potassium carbonate (2.91 g5 21.1 mmol), water (10.5 mL), 5-(2-bromo-4-chloro-6-fluorophenyl)-2-methyl-2H-tetrazole (3.38 g, 11.6 mmol) and additional palladium catalyst (0.385 g, 0.530 mmol) were added and the reaction was sealed again. After heating to 80 C for 1 hour, the reaction was cooled, quenched with water, and partitioned between EtOAc and water. The mixture was filtered through a plug of celite with EtOAc. The aqueous layer was extracted once with EtOAc. The combined organic layers were washed with additional water and then brine prior to drying over sodium sulfate. Filtration and solvent removal provided material which was subjected to chromatography on silica gel eluting with 0-15% EtOAc in hexanes to yield tert-hvcy ({5-[5-chloro-3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)phenyl]-3-fluoropyridin- 2-yl}methyl)carbamate. The above carbamate was dissolved in 50 mL of dry EtOAc. Anhydrous HCl gas was then bubbled through the solution for 3 minutes. The reaction was stirred vigorously for one hour. The reaction mixture was slowly neutralized with a saturated aqueous sodium bicarbonate solution. The mixture was partitioned between water and EtOAc. The organic layer was washed with water and brine prior to drying over sodium sulfate. The extracts were filtered, concentrated, and purified by chromatography on silica gel eluting with 0-20% MeOH in dichloromethane to provide ({5-[5-chloro-3- fluoro-2-(2-methyl-2Eta-tetrazol-5-yl)phenyl]-3-fluoropyridin-2-yl}methyl)amine.To a mixture of the above fluoropyridinium compound (1.02 g, 2.48 mmol), 1-hydroxy- cyclopentanecarboxylic acid (0.485 g, 3.72 mmol), (IH- 1,2,3 -benzotriazol-1 -yloxy)[tris(dimethyl- amino)]phosphonium hexafluorophosphate (1.76 g, 3.97 mmol) in anhydrous dichloromethane (16 mL) EPO <DP n="26"/>was added triethylamine (0.754 g, 7.45 mmol). The reaction mixture was allowed to stir at ambient temperature for 1 hour. After the reaction was judged complete by LC/MS analysis, the volume of the reaction is reduced in vacuo. The residue was taken up in EtOAc, and the organic phase was successively washed with water, 0.25 NHCl and saturated sodium bicarbonate solution. The combined extracts were dried over sodium sulfate, filtered, and concentrated. The crude material was subjected to chromatography on silica gel eluting with 0-50% EtOAc in hexanes to yield the title compound as a white solid, which gave a proton NuMR spectrum consistent with theory and a mass ion (ES+) of 449.2 for M+H+: 1H NuMR (500 MHz, CDCI3) delta 8.13 (s, IH), 7.87 (bs, NH), 7.34 (d, J= 8.8 Hz, IH), 7.26 (m,2H), 4.65 (d, J= 4.8 Hz, 2H), 4.35 (s, 3H), 2.23-2.21 (m, 3H), 1.85-1.84 (m, 4H), 1.77-1.74 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 25℃; | Step 1 : Preparation of C145. A solution of C144 (1.50g, 1 1.5mmol) (see Roussis, V., et al., Journal of Organic Chemistry 1988, 53, 201 1-2015) in dimethylformamide (20 mL) at room temperature was treated with potassium carbonate (2.07 g, 15.0 mmol) followed by benzyl bromide (1.50 mL, 12.7 mmol) and the mixture was stirred overnight at room temperature. The reaction mixture was treated with water and then extracted with diethyl ether. The aqueous layer was back extracted with diethyl ether. The combined organic layers were washed with water, brine and then dried over magnesium sulfate. The suspension was filtered, and concentrated in vacuo to give a colorless oil. Chromatography on silica gel with n-heptane-ethyl acetate (20% ethyl acetate) afforded C145 as a colorless oil. Yield: 2.36g, 10.7 mmol, 93%. 1H NMR (400 MHz, CDCI3) delta 7.39-7.30 (m, 5H), 5.20 (s, 2H), 3.04 (s, 1 H), 2.12-2.03 (m, 2H), 1.90-1.70 (m, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
.2 mL (25.9 mmol, 9 eq) of oxalyl chloride were added, drop-by-drop, to a solution, cooled to 0C, of 1 .13 g (8.7 mmol, 3 eq) of 1 -hydroxy-cyclopentanecarboxylic acid in 20 mL of tetrahydrofuran. The solution was agitated at 0C for 1 hour, and then at ambient temperature for 16 hours. The reaction mixture was evaporated dry. The residue was absorbed in dichloromethane and added to a solution of 500 mg (2.80 mmol, 1 eq) of 5- bromo-pyridin-3-ylamine in 20 ml of dichloromethane. 1.2 mL (8.6 mmol, 3 eq) of triethylamine was then added. The mixture was agitated at ambient temperature for 30 minutes. No initial product remained. The reaction mixture was poured into a frozen mixture of sodium and dichloromethane. The organic phase was extracted indichloromethane and then washed in water twice, then dried over sodium sulphate, and dry concentrated under vacuum. The residue was precipitated in dichloromethane and heptanes. 1 -hydroxy-cyclopentanecarboxylic acid (2-bromo-pyridin-4-yl)-amide was obtained in the form of a white solid.Melting point = 153C. NMR (1H, DMSO): 1.70-1 .76 (m, 6 H), 1 .95-2.03 (m, 2 H), 5.74 (s, 1 H), 7.81 -7.83 (dd, 1 H, J = 5.7, 1.9 Hz), 8.14 (d, 1 H, J = 1 .8 Hz), 8.23 (d, 1 H, J = 5.7 Hz), 10.35 (s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; | 8b (170 mg, 0.98 mmol), 1-hydroxycyclopentane-l- carboxylic acid (260 mg, 2.00 mmol), EDCi (288 mg, 1.50 mmol), and HO AT (204 mg, 1.50 rrmioi) were dissolved in /V A'-dimethylfomiamide (3 mL) and stirred, overnight at room temperature. The resulting solution was diluted with 10 ml, of 0 and extracted twice with ethyl acetate and the combined organic layers washed with brine. The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by flash-column chromatography using ethyl acetate/petroleum ether (1 :5) as eluent to give 8c (40 mg, 14%) as a yellow solid. MS (ES, m/z) 287 [M+H] . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With hydrogenchloride; In acetic acid; at 80℃; for 4h; | 8a (3 g, 16.36 mmol 1 .00 equiv) was dissolved in acetic acid (4 mL) and concentrated hydrogen chloride (4 mL). The resulting solution was stirred for 4 h at 80 C. The mixture was then concentrated under reduced pressure to give 8b (2 g, 94%) as a white solid, which was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | Example B9 A solution of cyclopentanone (2.0 g, 23.78 mmol) in DCM (30 mL) was treated with zinc chloride (0.5M in THF, 4.76 mL, 2.378 mmol) followed by trimethylsilyl cyanide (3.83 mL, 28.5 mmol) and stirred at RT overnight. The mixture was treated with satd. NaHCO3, extracted with DCM (1*) and the organic layer was washed with brine, dried over Na2SO4 and concentrated to dryness. The residue was treated with THF (5 mL) and HCl (2M, 4 mL), stirred at RT for 3 h, then the organics removed under reduced pressure. Additional HCl (12 M, 5 mL) was added, the mixture heated at 100 C. for 3 h, then cooled to RT, treated with water and extracted with EtOAc (2*). The combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford 1-hydroxycyclopentanecarboxylic acid (2.3 g, 74%). 1H NMR (400 MHz, DMSO-d6): delta 12.28 (s, 1H), 4.92 (s, 1H), 1.93-1.83 (m, 2H), 1.74-1.57 (m, 6H). | |
74% | Example B23 [0394] A solution of cyclopentanone (2.0 g, 23.78 mmol) in DCM (30 mL) was treated with zinc chloride (0.5M in THF, 4.76 mL, 2.378 mmol) followed by trimethylsilyl cyanide (3.83 mL, 28.5 mmol) and stirred at RT overnight. The mixture was treated with satd. NaHCO3, extracted with DCM (1×) and the organic layer was washed with brine, dried over Na2SO4 and concentrated to dryness. The residue was treated with THF (5 mL) and HCl (2M, 4 mL), stirred at RT for 3 h, then the organics removed under reduced pressure. Additional HCl (12 M, 5 mL) was added, the mixture heated at 100 C. for 3 h, then cooled to RT, treated with water and extracted with EtOAc (2×). The combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford 1-hydroxycyclopentanecarboxylic acid (2.3 g, 74%). 1H NMR (400 MHz, DMSO-d6): delta 12.28 (s, 1H), 4.92 (s, 1H), 1.93-1.83 (m, 2H), 1.74-1.57 (m, 6H). |
Tags: 16841-19-3 synthesis path| 16841-19-3 SDS| 16841-19-3 COA| 16841-19-3 purity| 16841-19-3 application| 16841-19-3 NMR| 16841-19-3 COA| 16841-19-3 structure
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