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CAS No. : | 91103-47-8 | MDL No. : | MFCD00191865 |
Formula : | C9H17NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GJDICGOCZGRDFM-ZCFIWIBFSA-N |
M.W : | 203.24 | Pubchem ID : | 637612 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.78 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 51.18 |
TPSA : | 64.63 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.96 cm/s |
Log Po/w (iLOGP) : | 2.67 |
Log Po/w (XLOGP3) : | 0.82 |
Log Po/w (WLOGP) : | 1.07 |
Log Po/w (MLOGP) : | 0.83 |
Log Po/w (SILICOS-IT) : | 0.39 |
Consensus Log Po/w : | 1.15 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.22 |
Solubility : | 12.2 mg/ml ; 0.0602 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.76 |
Solubility : | 3.54 mg/ml ; 0.0174 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.35 |
Solubility : | 9.1 mg/ml ; 0.0448 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.73 |
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 |
---|---|---|
85% | Stage #1: With diisobutylaluminium hydride In toluene at -78℃; for 1 h; Stage #2: With methanol In toluene at -78℃; for 0.166667 h; Stage #3: With methanol; water; citric acid In toluene at 0℃; for 1 h; |
Example 46(1-Methyl-2-oxo-ethyl)-carbamic acid tert-butyl ester The title compound from Example 45 (3.53 g, 17.4 mmol) was dissolved in toluene (35 mL) at -78° C. and DIBAL-H (26.6 mL, 39.9 mmol) was added dropwise over 1 hour. Methanol (70 mL) was added to the reaction over 10 min. at -78° C. The reaction was moved to an ice bath and 10percent w/v citric acid in water (250 mL) was added and the reaction was allowed to stir for 1 hour. The reaction was extracted with portions of ethyl acetate and the organic extracts were washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound (2.57 g, 85percent) as a white semi-solid.1H NMR (300 MHz, CDCl3): δ (ppm) 9.51 (s, 1H), 5.21 (broad s, 1H), 4.24 (broad s, 1H), 1.53 (s, 9H), 1.35 (d, 3H). |
82% | Stage #1: With diisobutylaluminium hydride In tetrahydrofuran; dichloromethane at -78℃; for 2 h; Stage #2: With water In tetrahydrofuran; dichloromethane at -78℃; |
Step 1: (R)-tert-butyl 1-oxopropan-2-ylcarbamateTo a cooled solution of (R)-methyl 2-(tert-butoxycarbonylamino)propanoate (40.0 g, 98.0 mmol) in DCM (200 mL) at -78° C. was added diisobutylaluminum hydride (208 mL, 1.0 M in THF) dropwise over 30 min. The reaction mixture was stirred at -78° C. for 1.5 h then quenched with water (50 mL). After warmed to rt, the white precipitate was removed by filtration over Celite. The organic layer was then washed with brine, dried (Na2SO4), and concentrated. The crude residue was purified by flash chromatography (petroleum ether: EtOAc, 10:1) to give (R)-tert-butyl 1-oxopropan-2-ylcarbamate (28.0 g, 82percent). 1H NMR (DMSO-d6, 400 MHz) δ 9.43 (s, 1H), 7.33 (d, J=6.0 Hz, 1H), 3.85 (m, 1H), 1.39 (s, 9H), 1.12 (d, J=7.2 Hz, 3H). |
65% | With diisobutylaluminium hydride In toluene at -78℃; for 2 h; | EXAMPLE 49; (R)-5-Chloro-thiophene-2-carboxylic acid (1 - {3-[4-(N,N-dimethyl-carbamimidoyl)-phenyl]- isoxazol-5-yl}-ethyl)-amide; Step l :; [0553] Methyl ester 8 (4.03 g, 19.9 mmol) was diluted with 40 mL of toluene and cooled to -780C. Diisobutylaluminum hydride in toluene (26 mL, 40 mmol) was added slowly to the precooled mixture down the side of the flask. The reaction was stirred at -780C for two hours at which time it was treated slowly with ca. 5 mL of methanol precooled to -780C (vigorous reaction). The mixture was then warmed to it and partitioned with saturated sodium potassium tartrate and ethyl acetate. The layers were separated, the organic phase was extracted with ethyl acetate and the combined organic layers were dried over MgSO4. After filtration and concentration in vacuo the crude material was purified by filtration through a short plug of silica gel eluted with dichloromethane affording the aldehyde 9 as a colorless oil (2.23g, 65percent). 1H NMR (DMSO-J6, 400 MHz): δ 9.38 (s, IH), δ 7.30 (d, IH), δ 3.79 (m, IH), δ 1.31 (s, 9H), 1.06 (d, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With sodium hydrogencarbonate In water at 20℃; | To a solution of D-alanine methyl ester hydrochloride (5 g, 35.8 mmol) and sodium hydrogen carbonate (9.0 g, 107 mmol) in water (100 mL) was added di-tert-butyl dicarbonate (11.7 g, 53.7 mmol) and the resulting solution was stirred at RTovernight. The reaction mixture was extracted with DCM (3 x 100 mL) and the combined organics were dried over MgSO4, filtered and concentrated under reduced pressure. Crude NMR revealed large amounts of un-reacted di-tert-butyl dicarbonate, hence the material was taken up in DCM (50 mL) and treated with N,N-dimethyl ethylenediamne (5 mL), and stirred for 30 mins. The solution waswashed with 1M HCI (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to afford 5.35 g (73percent yield) of the title compound as a colourless oi I.1H NMR (500 MHz, Chloroform-d) 6 5.04 (5, 1 H), 4.31 (m, 1 H), 3.73 (5, 3H), 1 .44 (5, 9H), 1.37 (d, J = 7.2 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25 h; Stage #2: for 18 h; |
Intermediate 57 Boc-D-AlaOMe Boc-D-AlaOH (10.0 g, 52.9 mmol) was dissolved in dry DMF (60 mL), then potassium carbonate (8.0 g, 58.0 mmol) was added, the mixture was stirred at rt for 15 min, and methyl iodide (6.58 mL, 106.0 mmol) was added dropwise. The stirring was maintained for 18h. Then, the mixture was concentrated in vacuo and the residue was dissolved in EtOAc (lOOmL). The organic layer was washed with water, brine, dried over MgSCU, filtered and concentrated. The crude product was purified by flash column chromatography (silica gel, DCM/MeOH 0 to 1percent) to give 10.36 g (51.0 mmol, 96percent yield) of the title compound. *Η NMR (DMSO-d6) δ 7.46 (1H, d), 4.35 (1H, m), 3.66 (3H, s), 1.30 (9H, s), 1.18 (3H, d). |
82% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; | Example 452-tert-Butoxycarbonylamino-propionic acid methyl ester Boc-D-Ala-OH (4.0 g, 21 mmol) and potassium carbonate (11.7 g, 84.6 mmol) was dissolved in dimethylformamide (90 mL) and iodomethane (1.6 mL, 25 mmol) was added to the reaction mixture. The reaction was allowed to stir at room temperature. overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with portions of water and brine, dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound as a colorless oil (3.53 g, 82percent).1H NMR (300 MHz, CDCl3): δ (ppm) 5.14 (broad s, 1 h), 4.33 (broad s, 1H), 3.51 (s, 3H), 1.49 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.91 % ee | With water In aq. phosphate buffer; N,N-dimethyl-formamide at 30℃; for 6 h; | General procedure: The soil samples were collected from various locations inChina, and then the strains were screened by utilizing N-Boc-2-aminobutyrate as a sole carbon source and selective platewith bromocresol purple indicator. Isolated strains weretransferred to 150 mL fermentation medium and cultivatedat 200 rpm, 30 °C for 48 h. After the cells were harvested, 1 g wet cell were washed and suspended in 5 mL 0.1 M,pH 7.0 potassium phosphate buffer (KPB). Cell suspensionswere mixed with 50 μL substrate solution (N-Boc-2-aminobutyrate:acetone = 1:4,V/V) and kept at 200 rpm, 30 °Cfor 6 h reaction, the enantioselective hydrolysis of the substratewas determined by GC-MS. The screening mediumcontained (per liter, pH 7) 0.5 g KCl, 0.5 g MgSO47H2O,1 g K2HPO43H2O, 3 g NaNO3,0.01 g FeSO4,0.25 g Bromocresolpurple, 20 g agar. Fermentation medium contained(per liter, pH 7) 0.5 g KCl, 0.5 g MgSO47H2O, 1 gK2HPO43H2O, 3 g NaNO3,0.01 g FeSO4,20 g sucrose. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.7 % ee | With lyophilized cells of Bacillus amyloliquefaciens WZZ002 In aq. phosphate buffer at 35℃; for 10 h; Enzymatic reaction | Enantioselective hydrolysis was performed on Boc-dl-Ala-OMe by adding both a substrate with a concentration range of 0.1 to 4.0M and a 500mg lyophilized cell of B. amyloliquefaciens WZZ002 in a 10mL (50mL flask) phosphate buffer solution (0.2M, pH6.0–12.0) at 20°C to 60°C. The solution was stirred at 400rpm. The pH level was controlled through automatic titration using different alkali solutions (2M). The samples were withdrawn at regular intervals and were immediately acidified with HCl (2M) to stop the reaction and to enhance the extractability of Boc-dl-Ala. The sample was extracted using ethyl acetate, whereas the organic phase was isolated and dried using anhydrous Na2SO4 for gas chromatography (GC) analysis. All experiments were conducted in triplicate, unless specified. The time course of enantioselective hydrolysis reaction was performed by adding 2M of Boc-dl-Ala-OMe and 5g of the lyophilized cell of B. amyloliquefaciens WZZ002 in 100mL (250mL flask) phosphate buffer solution (0.2M, pH8.0). The pH of the reaction was controlled through automatic titration using 6M of NH3·H2O to reduce the increasing amount of the neutralizer. |
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