Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 41014-93-1 | MDL No. : | MFCD11975325 |
Formula : | C5H10O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JRHWHSJDIILJAT-BYPYZUCNSA-N |
M.W : | 118.13 | Pubchem ID : | 6950703 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.8 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 29.08 |
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) : | -6.7 cm/s |
Log Po/w (iLOGP) : | 1.11 |
Log Po/w (XLOGP3) : | 0.45 |
Log Po/w (WLOGP) : | 0.23 |
Log Po/w (MLOGP) : | 0.01 |
Log Po/w (SILICOS-IT) : | -0.13 |
Consensus Log Po/w : | 0.33 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -0.66 |
Solubility : | 26.0 mg/ml ; 0.22 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.23 |
Solubility : | 7.02 mg/ml ; 0.0594 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.13 |
Solubility : | 159.0 mg/ml ; 1.34 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.54 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
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 |
---|---|---|
90% | ||
With diethyl ether | ||
In tetrahydrofuran at 0℃; Yield given; |
In diethyl ether | ||
0.34 g | In diethyl ether for 0.166667h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sulfuric acid; NaNO2 In water monomer at 0 - 20℃; | |
82% | With sulfuric acid; NaNO2 In water monomer at 0 - 5℃; for 1h; | |
With hydrogenchloride; acetic acid; NaNO2 |
With hydrogenchloride; silver(I) nitrite | ||
With hydrogenchloride; acetic acid; NaNO2 at 0 - 20℃; | ||
With sulfuric acid; NaNO2 In water monomer at 0℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium aluminium tetrahydride In diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With lithium aluminium tetrahydride In diethyl ether 1.) 0 deg C, then 3 h rt.; Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone for 24h; Heating; | |
With potassium carbonate In N,N-dimethyl-formamide for 14h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With potassium hydroxide; mercaptoethyl alcohol; sodium formate; 2-amino-2-hydroxymethyl-1,3-propanediol In water for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With lithium hydroxide In tetrahydrofuran; water for 1h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With NAD; hydrogen In hydrogenchloride for 35h; Ambient temperature; | |
With fructose 1,6-bisphosphate trisodium; nicotinamide adenine dinucleotide red. form; R171Y mutant In water at 25℃; other mutant enzyme; | ||
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 0 °C 1.2: tetrahydrofuran / 12 h / 20 °C 2.1: H2O2; aq. NaOH / tetrahydrofuran |
Multi-step reaction with 6 steps 1: Cl2CHOCH3 / CH2Cl2 / 1.) room temperature, 20 min, 2.) 50-55 deg C, 30 min 2: Et3N, DMAP / CH2Cl2 / 6 h / Ambient temperature 3: 92 percent / TFA / CH2Cl2 / 78 h / Heating 4: 99 percent / H2 / Pd/C / ethyl acetate / 2585.7 Torr 5: 59 percent / Na, liquid NH3 / tetrahydrofuran / 0.01 h 6: 1M H2SO4 / Heating | ||
Multi-step reaction with 6 steps 1: Cl2CHOCH3 / CH2Cl2 / 1.) room temperature, 20 min, 2.) 50-55 deg C, 30 min 2: Et3N, DMAP / CH2Cl2 / 6 h / Ambient temperature 3: TiCl4 / -40 °C 4: 99 percent / H2 / Pd/C / ethyl acetate / 2585.7 Torr 5: 59 percent / Na, liquid NH3 / tetrahydrofuran / 0.01 h 6: 1M H2SO4 / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With hydrogenchloride In tetrahydrofuran for 24h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With sulfuric acid In water at 90℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diisopinocampheylborane In tetrahydrofuran at 20℃; for 6h; Title compound not separated from byproducts.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran Title compound not separated from byproducts.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With N-ethyl-N,N-diisopropylamine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-(S)-hydroxyvaleric acid With sodium hydride In N,N-dimethyl-formamide Stage #2: 1-bromomethyl-4-bromobenzene In N,N-dimethyl-formamide at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: NaH / dimethylformamide 1.2: dimethylformamide / 20 °C 2.1: diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: NaH / dimethylformamide 1.2: dimethylformamide / 20 °C 2.1: diethyl ether 3.1: 70 percent / K2CO3; Pd(PPh3)4 / toluene / 7 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: NaH / dimethylformamide 1.2: dimethylformamide / 20 °C 2.1: diethyl ether 3.1: 70 percent / K2CO3; Pd(PPh3)4 / toluene / 7 h / 80 °C 4.1: 50 percent / aq. NaOH / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 70 percent / Huning's base 2: 95 percent / 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide; DMAP / CH2Cl2 3: 90 percent / MgBr2*Et2O / -20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 70 percent / Huning's base 2: 95 percent / 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide; DMAP / CH2Cl2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 70 percent / Huning's base 2: 95 percent / 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide; DMAP / CH2Cl2 3: 90 percent / MgBr2*Et2O / -20 °C 4: 95 percent / 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide / CH2Cl2 5: 55 percent / [(CF3)2MeCO]2Mo(=CHCMe2Ph)=N-2,6-(iPr)2C6H3 / benzene / 15 h / 60 °C 6: aq. HClO4 / methanol; tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 70 percent / Huning's base 2: 95 percent / 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide; DMAP / CH2Cl2 3: 90 percent / MgBr2*Et2O / -20 °C 4: 95 percent / 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide / CH2Cl2 5: 55 percent / [(CF3)2MeCO]2Mo(=CHCMe2Ph)=N-2,6-(iPr)2C6H3 / benzene / 15 h / 60 °C 6: aq. HClO4 / methanol; tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 70 percent / Huning's base 2: 95 percent / 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide; DMAP / CH2Cl2 3: 90 percent / MgBr2*Et2O / -20 °C 4: 95 percent / 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide / CH2Cl2 5: 55 percent / [(CF3)2MeCO]2Mo(=CHCMe2Ph)=N-2,6-(iPr)2C6H3 / benzene / 15 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 70 percent / Huning's base 2: 95 percent / 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide; DMAP / CH2Cl2 3: 90 percent / MgBr2*Et2O / -20 °C 4: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide / CH2Cl2 / 1 h / 20 °C 5: 90 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 18 h / 20 °C 6: 64 percent / aq. AcOH / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 62 percent / Et3N, DMAP / CH2Cl2 / 6 h / Ambient temperature 2: 87 percent / HCl / tetrahydrofuran; H2O / 3 h / Ambient temperature 3: KBH4 / methanol / 10 h / 0 °C 4: 74 percent / H2SO4 / H2O / 0.5 h / 90 °C | ||
Multi-step reaction with 5 steps 1: Et3N, DMAP / CH2Cl2 / 6 h / Ambient temperature 2: 92 percent / TFA / CH2Cl2 / 78 h / Heating 3: 99 percent / H2 / Pd/C / ethyl acetate / 2585.7 Torr 4: 59 percent / Na, liquid NH3 / tetrahydrofuran / 0.01 h 5: 1M H2SO4 / Heating | ||
Multi-step reaction with 5 steps 1: Et3N, DMAP / CH2Cl2 / 6 h / Ambient temperature 2: TiCl4 / -40 °C 3: 99 percent / H2 / Pd/C / ethyl acetate / 2585.7 Torr 4: 59 percent / Na, liquid NH3 / tetrahydrofuran / 0.01 h 5: 1M H2SO4 / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 99 percent / H2 / Pd/C / ethyl acetate / 2585.7 Torr 2: 59 percent / Na, liquid NH3 / tetrahydrofuran / 0.01 h 3: 1M H2SO4 / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 59 percent / Na, liquid NH3 / tetrahydrofuran / 0.01 h 2: 1M H2SO4 / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 92 percent / TFA / CH2Cl2 / 78 h / Heating 2: 99 percent / H2 / Pd/C / ethyl acetate / 2585.7 Torr 3: 59 percent / Na, liquid NH3 / tetrahydrofuran / 0.01 h 4: 1M H2SO4 / Heating | ||
Multi-step reaction with 4 steps 1: TiCl4 / -40 °C 2: 99 percent / H2 / Pd/C / ethyl acetate / 2585.7 Torr 3: 59 percent / Na, liquid NH3 / tetrahydrofuran / 0.01 h 4: 1M H2SO4 / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: K2CO3 / dimethylformamide / 14 h / Ambient temperature 2: N,N'-dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 0 °C 3: NaIO4 / dioxane; H2O / 3 h / Ambient temperature 4: K2CO3 / dimethylformamide / 14 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: K2CO3 / dimethylformamide / 14 h / Ambient temperature 2: N,N'-dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 0 °C 3: NaIO4 / dioxane; H2O / 3 h / Ambient temperature 4: 96 percent / 1 N LiOH / dioxane / 1 h / Ambient temperature 5: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: K2CO3 / dimethylformamide / 14 h / Ambient temperature 2: N,N'-dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 0 °C 3: NaIO4 / dioxane; H2O / 3 h / Ambient temperature 4: 96 percent / 1 N LiOH / dioxane / 1 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: K2CO3 / dimethylformamide / 14 h / Ambient temperature 2: N,N'-dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: K2CO3 / dimethylformamide / 14 h / Ambient temperature 2: N,N'-dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 0 °C 3: NaIO4 / dioxane; H2O / 3 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: K2CO3 / dimethylformamide / 14 h / Ambient temperature 2: N,N'-dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / tetrahydrofuran / 2 h / 0 °C 3: NaIO4 / dioxane; H2O / 3 h / Ambient temperature 4: 96 percent / 1 N LiOH / dioxane / 1 h / Ambient temperature 5: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / 0 °C 6: Et3N / tetrahydrofuran / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: diethyl ether 2: 3-(dimethylamino)propylamine / CCl4; benzene | ||
Multi-step reaction with 2 steps 1: tetrahydrofuran / 0 °C 2: 4-dimethylaminopyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 16 steps 1: 66 percent / LAH / diethyl ether / 1.) 0 deg C, then 3 h rt. 2: 1.) HBr; 2.) 50percent aq. KOH / 1.) AcOH, 1h; 2.) 120 deg C 3: aq. ethanol / 19 h / Heating 5: 83 percent / imidazole / dimethylformamide / 15 h / Ambient temperature 6: 95 percent / lithium borohydride, lithium triethylborohydride / diethyl ether; tetrahydrofuran / 3 h / Heating 7: pyridine / 3 h / 0 - 5 °C 8: 88 percent / NaI, NaHCO3 / acetone / 2 h / Heating 9: 86 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C 10: sodium acetate, bromine / 2 h / Ambient temperature 11: NaOH / methanol / 1 h / Ambient temperature 12: triethylamine / tetrahydrofuran / 2 h / 0 °C 13: DBU / benzene / 2 h / Heating 14: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature 15: 1.) m-CPBA; 2.) BF3*Et2O / 1.) CH2Cl2, 0 deg C, then rt.; 2.) 30 min, rt. 16: n-BuLi / tetrahydrofuran; hexane / 1 h / -60 °C | ||
Multi-step reaction with 16 steps 1: 66 percent / LAH / diethyl ether / 1.) 0 deg C, then 3 h rt. 2: 1.) HBr; 2.) 50percent aq. KOH / 1.) AcOH, 1h; 2.) 120 deg C 3: aq. ethanol / 19 h / Heating 5: 83 percent / imidazole / dimethylformamide / 15 h / Ambient temperature 6: 95 percent / lithium borohydride, lithium triethylborohydride / diethyl ether; tetrahydrofuran / 3 h / Heating 7: pyridine / 3 h / 0 - 5 °C 8: 88 percent / NaI, NaHCO3 / acetone / 2 h / Heating 9: 86 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C 10: sodium acetate, bromine / 2 h / Ambient temperature 11: NaOH / methanol / 1 h / Ambient temperature 12: triethylamine / tetrahydrofuran / 2 h / 0 °C 13: DBU / benzene / 2 h / Heating 14: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature 15: 1.) m-CPBA; 2.) BF3*Et2O / 1.) CH2Cl2, 0 deg C, then rt.; 2.) 30 min, rt. 16: n-BuLi, CO2 / tetrahydrofuran; hexane / 1 h / -60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 18 steps 1: 66 percent / LAH / diethyl ether / 1.) 0 deg C, then 3 h rt. 2: 1.) HBr; 2.) 50percent aq. KOH / 1.) AcOH, 1h; 2.) 120 deg C 3: aq. ethanol / 19 h / Heating 5: 83 percent / imidazole / dimethylformamide / 15 h / Ambient temperature 6: 95 percent / lithium borohydride, lithium triethylborohydride / diethyl ether; tetrahydrofuran / 3 h / Heating 7: pyridine / 3 h / 0 - 5 °C 8: 88 percent / NaI, NaHCO3 / acetone / 2 h / Heating 9: 86 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C 10: sodium acetate, bromine / 2 h / Ambient temperature 11: NaOH / methanol / 1 h / Ambient temperature 12: triethylamine / tetrahydrofuran / 2 h / 0 °C 13: DBU / benzene / 2 h / Heating 14: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature 15: 1.) m-CPBA; 2.) BF3*Et2O / 1.) CH2Cl2, 0 deg C, then rt.; 2.) 30 min, rt. 16: n-BuLi / tetrahydrofuran; hexane / 1 h / -60 °C 17: Ph3P, diethyl azodicarboxylate / tetrahydrofuran / 3 h / Ambient temperature 18: boron tribromide / CH2Cl2 / 0.5 h / -20 °C | ||
Multi-step reaction with 18 steps 1: 66 percent / LAH / diethyl ether / 1.) 0 deg C, then 3 h rt. 2: 1.) HBr; 2.) 50percent aq. KOH / 1.) AcOH, 1h; 2.) 120 deg C 3: aq. ethanol / 19 h / Heating 5: 83 percent / imidazole / dimethylformamide / 15 h / Ambient temperature 6: 95 percent / lithium borohydride, lithium triethylborohydride / diethyl ether; tetrahydrofuran / 3 h / Heating 7: pyridine / 3 h / 0 - 5 °C 8: 88 percent / NaI, NaHCO3 / acetone / 2 h / Heating 9: 86 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C 10: sodium acetate, bromine / 2 h / Ambient temperature 11: NaOH / methanol / 1 h / Ambient temperature 12: triethylamine / tetrahydrofuran / 2 h / 0 °C 13: DBU / benzene / 2 h / Heating 14: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature 15: 1.) m-CPBA; 2.) BF3*Et2O / 1.) CH2Cl2, 0 deg C, then rt.; 2.) 30 min, rt. 16: n-BuLi, CO2 / tetrahydrofuran; hexane / 1 h / -60 °C 17: Ph3P, diethyl azodicarboxylate / tetrahydrofuran / 3 h / Ambient temperature 18: boron tribromide / CH2Cl2 / 0.5 h / -20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 18 steps 1: 66 percent / LAH / diethyl ether / 1.) 0 deg C, then 3 h rt. 2: 1.) HBr; 2.) 50percent aq. KOH / 1.) AcOH, 1h; 2.) 120 deg C 3: aq. ethanol / 19 h / Heating 5: 83 percent / imidazole / dimethylformamide / 15 h / Ambient temperature 6: 95 percent / lithium borohydride, lithium triethylborohydride / diethyl ether; tetrahydrofuran / 3 h / Heating 7: pyridine / 3 h / 0 - 5 °C 8: 88 percent / NaI, NaHCO3 / acetone / 2 h / Heating 9: 86 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C 10: sodium acetate, bromine / 2 h / Ambient temperature 11: NaOH / methanol / 1 h / Ambient temperature 12: triethylamine / tetrahydrofuran / 2 h / 0 °C 13: DBU / benzene / 2 h / Heating 14: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature 15: 1.) m-CPBA; 2.) BF3*Et2O / 1.) CH2Cl2, 0 deg C, then rt.; 2.) 30 min, rt. 16: n-BuLi / tetrahydrofuran; hexane / 1 h / -60 °C 17: Ph3P, diethyl azodicarboxylate / tetrahydrofuran / 3 h / Ambient temperature 18: 71 percent / boron tribromide / CH2Cl2 / 0.5 h / -20 °C | ||
Multi-step reaction with 18 steps 1: 66 percent / LAH / diethyl ether / 1.) 0 deg C, then 3 h rt. 2: 1.) HBr; 2.) 50percent aq. KOH / 1.) AcOH, 1h; 2.) 120 deg C 3: aq. ethanol / 19 h / Heating 5: 83 percent / imidazole / dimethylformamide / 15 h / Ambient temperature 6: 95 percent / lithium borohydride, lithium triethylborohydride / diethyl ether; tetrahydrofuran / 3 h / Heating 7: pyridine / 3 h / 0 - 5 °C 8: 88 percent / NaI, NaHCO3 / acetone / 2 h / Heating 9: 86 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C 10: sodium acetate, bromine / 2 h / Ambient temperature 11: NaOH / methanol / 1 h / Ambient temperature 12: triethylamine / tetrahydrofuran / 2 h / 0 °C 13: DBU / benzene / 2 h / Heating 14: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature 15: 1.) m-CPBA; 2.) BF3*Et2O / 1.) CH2Cl2, 0 deg C, then rt.; 2.) 30 min, rt. 16: n-BuLi, CO2 / tetrahydrofuran; hexane / 1 h / -60 °C 17: Ph3P, diethyl azodicarboxylate / tetrahydrofuran / 3 h / Ambient temperature 18: 71 percent / boron tribromide / CH2Cl2 / 0.5 h / -20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 17 steps 1: 66 percent / LAH / diethyl ether / 1.) 0 deg C, then 3 h rt. 2: 1.) HBr; 2.) 50percent aq. KOH / 1.) AcOH, 1h; 2.) 120 deg C 3: aq. ethanol / 19 h / Heating 5: 83 percent / imidazole / dimethylformamide / 15 h / Ambient temperature 6: 95 percent / lithium borohydride, lithium triethylborohydride / diethyl ether; tetrahydrofuran / 3 h / Heating 7: pyridine / 3 h / 0 - 5 °C 8: 88 percent / NaI, NaHCO3 / acetone / 2 h / Heating 9: 86 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C 10: sodium acetate, bromine / 2 h / Ambient temperature 11: NaOH / methanol / 1 h / Ambient temperature 12: triethylamine / tetrahydrofuran / 2 h / 0 °C 13: DBU / benzene / 2 h / Heating 14: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature 15: 1.) m-CPBA; 2.) BF3*Et2O / 1.) CH2Cl2, 0 deg C, then rt.; 2.) 30 min, rt. 16: n-BuLi / tetrahydrofuran; hexane / 1 h / -60 °C 17: Ph3P, diethyl azodicarboxylate / tetrahydrofuran / 3 h / Ambient temperature | ||
Multi-step reaction with 17 steps 1: 66 percent / LAH / diethyl ether / 1.) 0 deg C, then 3 h rt. 2: 1.) HBr; 2.) 50percent aq. KOH / 1.) AcOH, 1h; 2.) 120 deg C 3: aq. ethanol / 19 h / Heating 5: 83 percent / imidazole / dimethylformamide / 15 h / Ambient temperature 6: 95 percent / lithium borohydride, lithium triethylborohydride / diethyl ether; tetrahydrofuran / 3 h / Heating 7: pyridine / 3 h / 0 - 5 °C 8: 88 percent / NaI, NaHCO3 / acetone / 2 h / Heating 9: 86 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C 10: sodium acetate, bromine / 2 h / Ambient temperature 11: NaOH / methanol / 1 h / Ambient temperature 12: triethylamine / tetrahydrofuran / 2 h / 0 °C 13: DBU / benzene / 2 h / Heating 14: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature 15: 1.) m-CPBA; 2.) BF3*Et2O / 1.) CH2Cl2, 0 deg C, then rt.; 2.) 30 min, rt. 16: n-BuLi, CO2 / tetrahydrofuran; hexane / 1 h / -60 °C 17: Ph3P, diethyl azodicarboxylate / tetrahydrofuran / 3 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 17 steps 1: 66 percent / LAH / diethyl ether / 1.) 0 deg C, then 3 h rt. 2: 1.) HBr; 2.) 50percent aq. KOH / 1.) AcOH, 1h; 2.) 120 deg C 3: aq. ethanol / 19 h / Heating 5: 83 percent / imidazole / dimethylformamide / 15 h / Ambient temperature 6: 95 percent / lithium borohydride, lithium triethylborohydride / diethyl ether; tetrahydrofuran / 3 h / Heating 7: pyridine / 3 h / 0 - 5 °C 8: 88 percent / NaI, NaHCO3 / acetone / 2 h / Heating 9: 86 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C 10: sodium acetate, bromine / 2 h / Ambient temperature 11: NaOH / methanol / 1 h / Ambient temperature 12: triethylamine / tetrahydrofuran / 2 h / 0 °C 13: DBU / benzene / 2 h / Heating 14: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature 15: 1.) m-CPBA; 2.) BF3*Et2O / 1.) CH2Cl2, 0 deg C, then rt.; 2.) 30 min, rt. 16: n-BuLi / tetrahydrofuran; hexane / 1 h / -60 °C 17: Ph3P, diethyl azodicarboxylate / tetrahydrofuran / 3 h / Ambient temperature | ||
Multi-step reaction with 17 steps 1: 66 percent / LAH / diethyl ether / 1.) 0 deg C, then 3 h rt. 2: 1.) HBr; 2.) 50percent aq. KOH / 1.) AcOH, 1h; 2.) 120 deg C 3: aq. ethanol / 19 h / Heating 5: 83 percent / imidazole / dimethylformamide / 15 h / Ambient temperature 6: 95 percent / lithium borohydride, lithium triethylborohydride / diethyl ether; tetrahydrofuran / 3 h / Heating 7: pyridine / 3 h / 0 - 5 °C 8: 88 percent / NaI, NaHCO3 / acetone / 2 h / Heating 9: 86 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C 10: sodium acetate, bromine / 2 h / Ambient temperature 11: NaOH / methanol / 1 h / Ambient temperature 12: triethylamine / tetrahydrofuran / 2 h / 0 °C 13: DBU / benzene / 2 h / Heating 14: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature 15: 1.) m-CPBA; 2.) BF3*Et2O / 1.) CH2Cl2, 0 deg C, then rt.; 2.) 30 min, rt. 16: n-BuLi, CO2 / tetrahydrofuran; hexane / 1 h / -60 °C 17: Ph3P, diethyl azodicarboxylate / tetrahydrofuran / 3 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 16 steps 1: 66 percent / LAH / diethyl ether / 1.) 0 deg C, then 3 h rt. 2: 1.) HBr; 2.) 50percent aq. KOH / 1.) AcOH, 1h; 2.) 120 deg C 3: aq. ethanol / 19 h / Heating 5: 83 percent / imidazole / dimethylformamide / 15 h / Ambient temperature 6: 95 percent / lithium borohydride, lithium triethylborohydride / diethyl ether; tetrahydrofuran / 3 h / Heating 7: pyridine / 3 h / 0 - 5 °C 8: 88 percent / NaI, NaHCO3 / acetone / 2 h / Heating 9: 86 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C 10: sodium acetate, bromine / 2 h / Ambient temperature 11: NaOH / methanol / 1 h / Ambient temperature 12: triethylamine / tetrahydrofuran / 2 h / 0 °C 13: DBU / benzene / 2 h / Heating 14: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature 15: 1.) m-CPBA; 2.) BF3*Et2O / 1.) CH2Cl2, 0 deg C, then rt.; 2.) 30 min, rt. 16: n-BuLi / tetrahydrofuran; hexane / 1 h / -60 °C | ||
Multi-step reaction with 16 steps 1: 66 percent / LAH / diethyl ether / 1.) 0 deg C, then 3 h rt. 2: 1.) HBr; 2.) 50percent aq. KOH / 1.) AcOH, 1h; 2.) 120 deg C 3: aq. ethanol / 19 h / Heating 5: 83 percent / imidazole / dimethylformamide / 15 h / Ambient temperature 6: 95 percent / lithium borohydride, lithium triethylborohydride / diethyl ether; tetrahydrofuran / 3 h / Heating 7: pyridine / 3 h / 0 - 5 °C 8: 88 percent / NaI, NaHCO3 / acetone / 2 h / Heating 9: 86 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C 10: sodium acetate, bromine / 2 h / Ambient temperature 11: NaOH / methanol / 1 h / Ambient temperature 12: triethylamine / tetrahydrofuran / 2 h / 0 °C 13: DBU / benzene / 2 h / Heating 14: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature 15: 1.) m-CPBA; 2.) BF3*Et2O / 1.) CH2Cl2, 0 deg C, then rt.; 2.) 30 min, rt. 16: n-BuLi, CO2 / tetrahydrofuran; hexane / 1 h / -60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1 61 g of S-α-hydroxyvaleric acid are obtained in the form of a light-yellow oil which still contains approximately 20% dioxan. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 2h; | 49.49.A.a; 49.49.A.b Example 49-A. b). Ethyl 5-ethyl-1 -(6-(3-((3-ethyl-4-(1 -((S)-2-hydroxypentanoyl)piperidin-4- yl)phenyl)amino)-2,3-dihydro-1 H-inden-4-yl)pyridin-2-yl)-1 H-pyrazole-4-carboxylate (diastereomer-1) and ethyl 5-ethyl-1 -(6-(3-((3-ethyl-4-(1 -((S)-2-hydroxypentanoyl)piperidin- 4-yl)phenyl)amino)-2,3-dihydro-1 H-inden-4-yl)pyridin-2-yl)-1 H-pyrazole-4-carboxylate (diastereomer-2). General procedure: Example 45-C. a) (±)-Ethyl 1 -(6-(3-((4-(1 -(cyclobutanecarbonyl)piperidin-4-yl)-2- methylphenyl)amino)-2,3-dihydro-1 H-inden-4-yl)pyridin-2-yl)-5-methyl-1 H-pyrazole-4- carboxylate; HATU (94 mg, 0.246 mmol) was added to a solution of (±)-ethyl 5-methyl-1 -(6-(3- ((2-methyl-4-(piperidin-4-yl)phenyl)amino)-2,3-dihydro 4-carboxylate (120 mg, 0.224 mmol), DIPEA (1 17 μΙ_, 0.672 mmol), and cyclobutanecarboxylic acid (18.32 μΙ_, 0.220 mmol) in DMF (2.2 ml_). The mixture was then stirred for 2 h, and then diluted with H20/brine (ca. 1/1) and EtOAc. The bi-layer was then separated. The aqueous layer was then extracted with EtOAc. The combined organic layers were washed with brine, dried, and concentrated to firnish the title compound. MS (ESI+) m/z 618.5 (M+H).; Example 49. Example 49-A. a). Ethyl 5-ethyl-1 -(6-(3-((3-ethyl-4-(1 -((S)-2-hydroxypentanoyl)piperidin-4- yl)phenyl)amino)-2,3-dihydro- H-pyrazole-4-carboxylate; The title compound was synthesized analogously to the preparation of ethyl 5-ethyl-1 -(6- (3-((3-ethyl-4-(1 -((S)-2-hydroxypropanoyl)piperidin-4-yl)phenyl)amino)-2,3-dihydro-1 H-inden-4- yl)pyridin-2-yl)-1 H-pyrazole-4-carboxylate (Example 48-B. a)) but using (S)-2-hydroxypentanoic acid in the place of L-(+)-lactic acid. MS (ESI+) m/z 664.4 (M+H).; Resolution of the diastereomers of ethyl 5-ethyl-1 -(6-(3-((3-ethyl-4-(1 -((S)-2- hydroxypentanoyl)piperidin-4-yl)phenyl)amino)-2,3-dihydro-1 H-inden-4-yl)pyridin-2-yl)-1 H- pyrazole-4-carboxylate was achieved by chiral HPLC using CHIRALPAK IA column with 65% hexane with 0.1 % DEA in EtOH to give ethyl 5-ethyl-1 -(6-(3-((3-ethyl-4-(1 -((S)-2- hydroxypentanoyl)piperidin-4-yl)phenyl)amino)-2,3-dihydro-1 H-inden-4-yl)pyridin-2-yl)-1 H- pyrazole-4-carboxylate (diastereomer-1) (tr = 7.5 min) and ethyl 5-ethyl-1 -(6-(3-((3-ethyl-4-(1 - ((S)-2-hydroxypentanoyl)piperidin-4-yl)phenyl)amino)-2,3-dihydro-1H-inden-4-y 1H-pyrazole-4-carboxylate (diastereomer-2) (tr = 10.2 min). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
> 99 % ee | With D-lactate oxidase from Gluconobacter oxydans 621H; oxygen; catalase In aq. buffer at 30℃; for 12h; Resolution of racemate; Enzymatic reaction; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: (2S)-2-hydroxypentanoic acid With O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere; Stage #2: 2-amino-5-bromo-N-ethylbenzamide With triethylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate / N,N-dimethyl-formamide / 0.17 h / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: iodine / dichloromethane / 0.33 h 2.2: 16 h / 50 °C 3.1: N,N,N-tributylbutan-1-aminium fluoride / tetrahydrofuran / 0.5 h / 0 °C 4.1: 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / 2 h / -78 °C 4.2: 2 h / -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate / N,N-dimethyl-formamide / 0.17 h / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: iodine / dichloromethane / 0.33 h 2.2: 16 h / 50 °C 3.1: N,N,N-tributylbutan-1-aminium fluoride / tetrahydrofuran / 0.5 h / 0 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / -78 °C 5.1: acetonitrile / 24 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate / N,N-dimethyl-formamide / 0.17 h / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: iodine / dichloromethane / 0.33 h 2.2: 16 h / 50 °C 3.1: N,N,N-tributylbutan-1-aminium fluoride / tetrahydrofuran / 0.5 h / 0 °C 4.1: 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / 2 h / -78 °C 4.2: 2 h / -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate / N,N-dimethyl-formamide / 0.17 h / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: iodine / dichloromethane / 0.33 h 2.2: 16 h / 50 °C 3.1: N,N,N-tributylbutan-1-aminium fluoride / tetrahydrofuran / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate / N,N-dimethyl-formamide / 0.17 h / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: iodine / dichloromethane / 0.33 h 2.2: 16 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate / N,N-dimethyl-formamide / 0.17 h / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: iodine / dichloromethane / 0.33 h 2.2: 16 h / 50 °C 3.1: N,N,N-tributylbutan-1-aminium fluoride / tetrahydrofuran / 0.5 h / 0 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / -78 °C |
[ 13748-90-8 ]
(S)-2-Hydroxy-4-methylpentanoic acid
Similarity: 0.92
[ 20312-37-2 ]
(R)-2-Hydroxy-4-methylpentanoic acid
Similarity: 0.92
[ 299-28-5 ]
Calcium (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoate
Similarity: 0.88
[ 527-07-1 ]
Sodium (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoate
Similarity: 0.88
[ 13748-90-8 ]
(S)-2-Hydroxy-4-methylpentanoic acid
Similarity: 0.92
[ 20312-37-2 ]
(R)-2-Hydroxy-4-methylpentanoic acid
Similarity: 0.92
[ 299-28-5 ]
Calcium (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoate
Similarity: 0.88
[ 527-07-1 ]
Sodium (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoate
Similarity: 0.88
[ 13748-90-8 ]
(S)-2-Hydroxy-4-methylpentanoic acid
Similarity: 0.92
[ 20312-37-2 ]
(R)-2-Hydroxy-4-methylpentanoic acid
Similarity: 0.92
[ 133-37-9 ]
(2R,3R)-rel-2,3-Dihydroxysuccinic acid
Similarity: 0.88
[ 87-69-4 ]
(2R,3R)-2,3-Dihydroxysuccinic acid
Similarity: 0.88