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CAS No. : | 261165-05-3 | MDL No. : | MFCD01320857 |
Formula : | C11H19NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RNJQBGXOSAQQDG-JGVFFNPUSA-N |
M.W : | 229.27 | Pubchem ID : | 1512529 |
Synonyms : |
BOC-(1S,3R)-3-Aminocyclopentanecarboxylic acid
|
Chemical Name : | (1S,3R)-3-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid |
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.82 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 59.16 |
TPSA : | 75.63 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) : | -6.73 cm/s |
Log Po/w (iLOGP) : | 2.08 |
Log Po/w (XLOGP3) : | 1.37 |
Log Po/w (WLOGP) : | 1.76 |
Log Po/w (MLOGP) : | 1.03 |
Log Po/w (SILICOS-IT) : | 0.55 |
Consensus Log Po/w : | 1.36 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.79 |
Solubility : | 3.68 mg/ml ; 0.016 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.56 |
Solubility : | 0.63 mg/ml ; 0.00275 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.14 |
Solubility : | 16.6 mg/ml ; 0.0724 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.98 |
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: |
* 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 |
---|---|---|
99% | With hydrogen In methanol for 1 h; | The acid prepared in Step A (230 g, 1.0 mol) and 10 percent Pd/C (5.0 G) in 500 ML of methanol on a Parr shaker was HYDROGENATED under 50 psi of hydrogen for 1 h. The catalyst was removed by filtration and the filtrate was evaporated. The residue was dissolved in dichloromethane and dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated and dried under vacuum. The title compound was obtained as a light yellow solid (230 g, 99 percent). LC-MS for C11H19N04 [M+H+] CALCULATED 230, found 230. |
99% | With hydrogen In methanol for 1 h; | The acid (Step A, Procedure A, Intermediate 5) (227 g, 1.0 mol) and 10percent Pd/C (5.0 g) in 500 mL of methanol on a Parr shaker was hydrogenated under 50 lb of hydrogen for one hour. The catalyst was removed by filtration and the filtrate was evaporated. The residue was dissolved in dichloromethane and dried over anhydrous sodium sulfate. After filtered, the filtrate was evaporated and dried in vacuum. The title compound was obtained as a light yellow solid (226.0 g, 99 percent). LC-MS for C1 lH19NO4 [MF calculated 230, found 230. |
99% | With hydrogen In methanol for 1 h; | Step B; The solution of the acid (Step A, Procedure A, Intermediate 4) (227 g, 1.0 mol) and 10percent Pd/C (5.0 g) in 500 mL of methanol was hydrogenated under 50 lb of hydrogen for one hour. The catalyst was removed by filtration and the filtrate was evaporated to dryness. The residue was dissolved in dichloromethane and dried over anhydrous sodium sulfate. The filtrate was evaporated to dryness and dried in vacuum. The title compound was obtained as a light yellow solid (226.0 g, 99percent). LC-MS for C11H19NO4 [M+H+] calculated 230, found 230.; Step B The acid prepared in Step A (230 g, 1.0 mol) and 10percent Pd/C (5.0 g) in 500 mL of methanol was placed on a Parr apparatus and hydrogenated under 50 psi of hydrogen for 1 h. The catalyst was removed by filtration and the filtrate was evaporated. The residue was dissolved in dichloromethane and dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated and dried under vacuum. The title compound was obtained as a light yellow solid (230 g, 99percent). LC-MS for C11H19NO4 calculated 229, found [M+H]+ 230. |
99% | With hydrogen In methanol for 1 h; | The acid (Step A, Procedure A, Intermediate 5) (227 g, 1.0 mol) and 10percent Pd/C (5.0 g) in 500 mL of methanol on a Parr shaker was hydrogenated under 50 lb of hydrogen for one hour. The catalyst was removed by filtration and the filtrate was evaporated. The residue was dissolved in dichloromethane and dried over anhydrous sodium sulfate. After filtered, the filtrate was evaporated and dried in vacuum. The title compound was obtained as a light yellow solid (226.0 g, 99 percent). LC-MS for C11H19NO4 [M+H+] calculated 230, found 230. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With N-ethyl-N,N-diisopropylamine In 1,4-dioxane; water at 20 - 27℃; for 3 h; | di-tert-l3utyl dicarbonate (1.25 g, 5.75 mmol) and DIPEA (2.61 mE, 15.0 mmol) were added to a solution of (1 S,3R)-3-aminocyclopentanecarboxylic acid (0.646 g, 5.0 mmol) in 1,4-dioxane (5 mE) and water (5 mE) and the resulting mixture was stirred at RT for 3 h. The reaction mixture was acidified to pH 2 using 1 M aqueous HC1 and extracted with DCM (x4). The combined organic extractswere passed through a phase separator cartridge and con-centrated in-vacuo to give (1 S,3R)-3-[(tert-butoxycarbonyl) amino]cyclopentanecarboxylic acid (1.13 g, 99percent). ‘H NMR (400 MHz, CDC13) ö: 1.44 (s, 9H),1.56-2.06 (m, 5H), 2.16-2.33 (m, 1H), 2.79-2.93 (m, 1H),3.87-4.18 (m, 1H), 4.86 (bt s., 1H). One exchangeable proton not observed. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.2% | Stage #1: With potassium carbonate In tetrahydrofuran; water at 0℃; Stage #2: at 20℃; for 20 h; Stage #3: With acetic acid In tetrahydrofuran; water |
Step C: Preparation of (1S,3R)-Cyclopentanecarboxylic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]. Aqueous potassium carbonate (2.20 g, 15.7 mmol) in water (20 ml) was added to a suspension of (1S,3R)-3-aminocyclopentanecarboxylic acid hydrochloride (1.30 g, 7.85 mmol) in THF (20 ml) at 0° C., stirred for 15 min and Boc-anhydride (2.70 ml, 11.8 mmol) was added. The reaction mixture was warmed to room temperature and stirred for 20 h. The reaction mixture was acidified with 10percent acetic acid to a pH of 4.0-5.0 and extracted with ethyl acetate (2.x.30 ml). The combined organic layer was washed successively with water, brine, dried over anhydrous sodium sulfate and concentrated to afford 1.30 g (72.2percent) of (1S,3R)-cyclopentanecarboxylic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino] as pale yellow liquid. |
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