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CAS No. : | 147266-92-0 | MDL No. : | MFCD01861341 |
Formula : | C10H17NO5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BENKAPCDIOILGV-NKWVEPMBSA-N |
M.W : | 231.25 | Pubchem ID : | 688615 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.8 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 59.53 |
TPSA : | 87.07 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) : | -7.53 cm/s |
Log Po/w (iLOGP) : | 1.75 |
Log Po/w (XLOGP3) : | 0.25 |
Log Po/w (WLOGP) : | 0.06 |
Log Po/w (MLOGP) : | -0.07 |
Log Po/w (SILICOS-IT) : | -0.64 |
Consensus Log Po/w : | 0.27 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.17 |
Solubility : | 15.7 mg/ml ; 0.068 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.64 |
Solubility : | 5.31 mg/ml ; 0.023 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.43 |
Solubility : | 621.0 mg/ml ; 2.69 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.14 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H319 | 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 |
---|---|---|
25.3% | With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In Isopropyl acetate; water at 0 - 20℃; for 1 h; | To a solution of (2R,4S)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (20 g, 86.6 mmol) in isopropylacetate (100 mL) was added TEMPO (675 mg, 4.3 mmol) at 0° C. A solution of aq. NaClO (10 wt percent, 61.8 g, 104.0 mmol) was added dropwise to the reaction mixture at 0-5° C. The reaction was allowed to warm to room temperature and stirred at room temperature for 1 hr. The organic layer was separated and the aqueous layer was treated with 1 M aq. KHSO4solution and extracted with isopropyl acetate (2×30 mL). The combined organic layers were washed with 5percent Na2S2O3(100 mL), brine, dried over anhydrous Na2SO4, filtered and evaporated. The residue was triturated with acetonitrile (20 mL), filtered and concentrated to give the title compound (5.0 g, 25.3percent yield) as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium hydroxide In 1,4-dioxane at 0 - 20℃; | Preparation 1: Methyl (25,45)-l-Boc-4-aminopyrrolidin-2-carboxyIate [285] Step A: (4/?)-l-Boc-4-hydroxy-L-proline [286] (4/?)-hydroxy-L-proline (5.08 g, 38.77 mmol) was dissolved in IN NaOH (40 ml) and 1,4-dioxane (40 ml), and to the resulting solution, di-t-butyl dicarbonate (9.3g, 42.6 mmol) was added dropwise at 00C. The reaction mixture was stirred at room tem.not. perature for 8 hours, concentrated in vacuo, acidified with IN HCl, and extracted with EtOAc. The organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give the title compound (8.84g, 99 percent).[287] MS[M+H] = 232 (M+l) [288] [289] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11 g | With triethylamine In methanol for 2 h; Reflux | A) (2R,4S)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid A mixture of (2R,4S)-4-hydroxypyrrolidine-2-carboxylic acid (7.1 g), di-tert-butyl dicarbonate (25 mL), triethylamine (14 mL) and methanol (130 mL) was heated with reflux for 2 hr. The mixture was allowed to be cooled to room temperature, and the solvent was evaporated under reduced pressure. To the residue was added sodium dihydrogenphosphate (590 mg) at 0°C, and the mixture was acidified (pH=2) with dilute hydrochloric acid. The mixture was stirred at 0°C for 30 min, and extracted with ethyl acetate/2-propanol (5:1). The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (11 g). 1H NMR (300 MHz, CDCl3) δ 1.40-1.52 (9H, m), 2.07-2.43 (2H, m), 3.43-3.68 (2H, m), 4.34-4.57 (2H, m), 5.00 (2H, brs). |
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