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CAS No. : | 7536-55-2 | MDL No. : | MFCD00038152 |
Formula : | C9H16N2O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FYYSQDHBALBGHX-YFKPBYRVSA-N |
M.W : | 232.23 | Pubchem ID : | 82035 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.67 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 54.57 |
TPSA : | 118.72 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) : | -8.14 cm/s |
Log Po/w (iLOGP) : | 0.99 |
Log Po/w (XLOGP3) : | -0.59 |
Log Po/w (WLOGP) : | -0.16 |
Log Po/w (MLOGP) : | -0.48 |
Log Po/w (SILICOS-IT) : | -0.91 |
Consensus Log Po/w : | -0.23 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -0.45 |
Solubility : | 83.1 mg/ml ; 0.358 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.43 |
Solubility : | 8.59 mg/ml ; 0.037 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.26 |
Solubility : | 129.0 mg/ml ; 0.555 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.86 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | 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 |
---|---|---|
91% | With sodium carbonate In 1,4-dioxane; water at 20℃; | L-asparagine (15 g, 0.113 mol, LEQ.) and sodium carbonate (12 g, 0.113 mol) were dissolved in water (225 ML) and 1, 4-dioxane (225 ml) at r. T.. To this solution, di-tert-butyl-dicarbonate (30 g, 0.137 mol, 1.2 eq. ) was added and the mixture was stirred overnight. The solvent was evaporated under reduced pressure till 1,4-dioxane was distilled and the pH adjusted to 2 with HCI 37percent to give a white solid that was filtered, washed with water and dried. Yield 91percent. 24g. Analytical data: m. p. 175°C-180°C (lit. 175°C). 'H NMR (DMSO-D6) 12.5 (1H, br); 7.31 (1H, BR) ; 6.91 (1H, br); 6.87 (1H, d, J=8. 4 Hz); 4.23 (1H, q, J=7. 7 HZ) ; 2.56-2. 36 (2H, M) ; 1.38 (9H, s). |
91% | Stage #1: With sodium carbonate In 1,4-dioxane; water at 20℃; Stage #2: With hydrogenchloride In water |
L-asparagine (15 g, 0.113 mol, 1 eq.) and sodium carbonate (12 g, 0.113 mol) were dissolved in water (225 ml) and 1,4-dioxane (225 ml) at r.t. To this solution, di-tert-butyl-dicarbonate (30 g, 0.137 mol, 1.2 eq.) was added and the mixture was stirred overnight. The solvent was evaporated under reduced pressure until 1,4-dioxane was distilled and the pH adjusted to 2 with HCl 37percent to give a white solid that was filtered, washed with water and dried. Yield 91percent. 24 g. Analytical data: m.p. 175° C.-180° C. (lit. 175° C.). 1H NMR (DMSO-d6) 12.5 (1H, br); 7.31 (1H, br); 6.91 (1H, br); 6.87 (1H, d, J=8.4 Hz); 4.23 (1H, q, J=7.7 Hz); 2.56-2.36 (2H, m); 1.38 (9H, s). |
64% | With sodium hydroxide In 1,4-dioxane; water at 10 - 20℃; | General procedure: To a solution containing L-asparagine monohydrate (1a) (15 g, 0.10 mol) in a mixture of 1 M sodium hydroxide (100 mL) and water (180 mL) was added a solution containing di-t-butyloxydicarbonate (24 g, 0.11 mol) in 1,4-dioxane (170 mL) dropwise with stirring at 10 °C. After overnight stirring at room temperature, the reaction mixture was evaporated in vacuo to anoily product, which was cooled and acidified to pH 2 with 10 percent potassium hydrogen sulfate to give a precipitate. The precipitate was filtered, washed with water and recrystallizedwith 500 mL ethanol to give 14.8 g of crystals (64 percent). m.p.177-179 °C (lit. 20) 181-182). 1H NMR (DMSO-d6): d = 1.38ppm (9H, s, CH3), 2.09 (1H, s, NH), 2.48 (2H, d, CH2), 4.22(1H, q, CH), 6.88 (2H, d, NH2). IR (KBr, nmax, cm-1): 1720(COOH), 1690 (amide I), 1663 (amide II (side chain)), 1591(amide II (side chain)), 1535 (amide II). Elemental analysis:Calcd. for C9H16N2O5: C, 46.54; H, 6.94; N, 12.07 percent. Found:C, 46.70; H, 7.05; N, 11.99 percent. [a]D15-7.8° (c = 1.22, DMF) (lit.21) [aD]20 -7.8 (c = 1, DMF)). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90 %Chromat. | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 12 h; Inert atmosphere | General procedure: To a stirred solution of N-protected-L-asparagin 1a-c (0.10 mmol) and alcohol or amine 2a-n (0.12 mmol) inDCM (5 mL), EDC.HCl (0.30 mmol) and DMAP (0.02 mmol) were added at 0 oC. This reaction mixture was stirred for 12h at room temperature. Then the reaction mixture was poured in H2O (10 mL) and extracted with DCM (20 mL). The organic phase was separated, dried, and subjected to flash column chromatography (EtOAc–hexane, 1: 4) to afford the desired compounds as white solids. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With [bis(acetoxy)iodo]benzene In water; ethyl acetate; acetonitrile at 16 - 20℃; for 4.5 h; | N-Boc-L-asparagine (13; 3.48 g, 15 mmol) and PIDA (5.81 g, 18 mmol)were dissolved in a mixture of EtOAc, MeCN, and H2O (2:2:1, 62.5 mL)and stirred at 16 °C for 30 min. Afterwards, the reaction mixture wasallowed to warm up to r.t. and stirred for 4 h whereupon a precipitatewas formed, which was collected by filtration and dried; yield: 2.02 g(66percent, 9.89 mmol); colorless solid; mp 211–213 °C (Lit.25 mp 216 °C).1H NMR (500 MHz, DMSO-d6): δ = 1.40 [s, 9 H, C(CH3)3], 2.76 (dd,3J = 9.2 Hz, 2J = 11.8 Hz, 1 H, CH2), 3.06 (dd, 3J = 5.1 Hz, 2J = 11.8 Hz, 1H, CH2), 3.65–3.69 (m, 1 H, COCH), 6.08 (s, 1 H, OCONH). Protons ofCO2H and the NH2 group were not detected.13C NMR (125 MHz, DMSO-d6): δ = 28.3, 40.8, 51.1, 78.2, 155.2, 171.2.LC-MS (ESI): 100percent purity; m/z = 205.19 ([M + H]+), 203.09 ([M – H]–).HRMS (ESI+): m/z calcd for C8H16N2O4 ([M + H]+): 205.1183; found:205.1177. |
57% | With [bis(acetoxy)iodo]benzene In water; ethyl acetate; acetonitrile at 5 - 25℃; for 3 - 4 h; | N-tert-butoxycarbonyl-L-asparagine, from step 1 of Example G. 5 or commercially available, (8 g, 0.034 mol, leq. ) was suspended in ethyl acetate (72 ml), acetonitrile (72ml) and water (36ml), and IODOBENZENEDIACETATE (13,3 g, 0. 041 mol, 1,2 eq. ) was added at 5°C. The mixture was stirred at 10°-25°C for 3-4h, then a white solid came off.. The solid was filtered, washed with diethyl ether and dried under vacuum to give a white powder. Yield 57percent. 4g. Analytical data: m. p. 210°C-211°C. Silica gel (dicloromethane/methanol/acetic acid 5/3/1) RF 0, 5. H NMR (DMSO-d6) 4.15 (1H, t); 3.15 (2H, M) ; 1.45 (9H, s); |
57% | With [bis(acetoxy)iodo]benzene In water; ethyl acetate; acetonitrile at 5 - 25℃; for 3 - 4 h; | N-tert-butoxycarbonyl-L-asparagine, from step 1 of Example G.5 or commercially available, (8 g, 0.034 mol. 1 eq.) was suspended in ethyl acetate (72 ml), acetonitrile (72 ml) and water (36 ml), and iodobenzenediacetate (13.3 g, 0.041 mol. 1.2 eq.) was added at 5° C. The mixture was stirred at 10°-25° C. for 3-4 h, then a white solid came off. The solid was filtered, washed with diethyl ether and dried under vacuum to give a white powder. Yield 57percent.4 g. Analytical data: m.p. 210° C.-211° C. Silica gel (dicloromethane/methanol/acetic acid 5/3/1) Rf 0.5. 1H NMR (DMSO-d6) 4.15 (1H, t); 3.15 (2H, m); 1.45 (9H, s); |
[ 84787-81-5 ]
(S)-Ethyl 4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate
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