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CAS No. : | 52-90-4 | MDL No. : | |
Formula : | C3H7NO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XUJNEKJLAYXESH-REOHCLBHSA-N |
M.W : | 121.16 | Pubchem ID : | 5862 |
Synonyms : |
Cysteine;L-Cys;Cysteinum;FEMA No. 3263;NSC 8746;(R)-Cysteine;L-(+)-Cysteine
|
Num. heavy atoms : | 7 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.67 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 28.94 |
TPSA : | 102.12 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) : | -8.81 cm/s |
Log Po/w (iLOGP) : | 0.37 |
Log Po/w (XLOGP3) : | -2.49 |
Log Po/w (WLOGP) : | -0.67 |
Log Po/w (MLOGP) : | -3.06 |
Log Po/w (SILICOS-IT) : | -0.69 |
Consensus Log Po/w : | -1.31 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 3.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 1.11 |
Solubility : | 1560.0 mg/ml ; 12.9 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 0.89 |
Solubility : | 936.0 mg/ml ; 7.73 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | 0.59 |
Solubility : | 470.0 mg/ml ; 3.88 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.75 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P501-P270-P264-P301+P312+P330 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
68 g | Stage #1: With sodium hydroxide In ethanol at 20℃; for 0.166667 h; Stage #2: at 20℃; for 6 h; |
(1 mol) was homogeneously dispersed in 3 L of absolute ethanol, and 3.5 mol of sodium hydroxide solution (20 mol / L) was added dropwise under magnetic stirring at room temperature and stirring was continued for 10 min. 1.1 moles of allyl bromide and reacted at room temperature for 6 h to form a crude solution of deoxythioallyl cysteine sulfoxide (2-PeCS).The solution was transferred to a clean container and adjusted to pH 5.5.4 ° C for 12 h at 30 ° C to form a white deoxy 2-PeCS crystal.(2) The 2-PeCS crystal obtained in step (1) was filtered, dried at 50 ° C, and then redissolved in 10 mL of distilled water containing 1percent glacial acetic acid and heated to boiling.The solution was poured into 150 mL of boiling ethanol and recrystallized.The solution was allowed to stand at 12 ° C for 12 h and the crystals were collected by filtration and dried at 50 ° C to give about 69 g of pure 2-PeCS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.1 mg | at 80℃; for 24 h; Sealed tube | Aliin(Manufactured by Funakoshi Co., Ltd.) and 24.2 mg of L-cysteine (Wako Pure Chemical Industries, Ltd.) were dissolved in 10 mL of water, placed in a plastic container, sealed, kept at 80 ° C. and reacted for 24 hours . After completion of the reaction, this solution was measured using LC / TOF-MS (microTOF 2-kp manufactured by Bruker-Dartonics) to find a mass of 162.0583 as [M + H] + to produce S-allyl cysteine It was confirmed that it was doing. The content of S-allyl cysteine in the aqueous solution was analyzed by HPLC, and it was 0.28 mg / ml. Furthermore, S-allyl cysteine was purified from this aqueous solution using preparative HPLC to obtain 2.1 mg of a white powder, and its purity was analyzed by HPLC,It was 98percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | Stage #1: With hydrogenchloride In diethyl ether; water for 3 h; Stage #2: With sodium hydroxide In diethyl ether; water at 20℃; for 2 h; |
(Step 1)To a mixed solution of diethyl ether (400 ml) and conc. hydrochloric acid (400 ml) was added in drops 4-methoxybenzyl chloride (280 g, 1780 mmol) dissolved in diethyl ether (400 ml) for 2 h, and the mixture was stirred for 1 h. The organic layer was separated and added to a solution which was prepared by dissolving L-cysteine (197 g, 1625 mmol) and 2N aqueous sodium hydroxide solution (980 ml) in ethanol (1890 ml). The mixture was stirred for 2 h at room temperature. After completion of the reaction, the mixture was cooled to 0, and neutralized to pH 7 using 3N aqueous hydrochloric acid solution. The resulting solid was filtered and dried to give (R)-2-amino-3-(4-methoxy-benzylsulfanyl)-propionic acid (250 g, 1035 mmol, Yield 64percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | Stage #1: With hydrogenchloride In diethyl ether; water for 3 h; Stage #2: With sodium hydroxide In diethyl ether; ethanol; water at 20℃; for 2 h; Stage #3: With hydrogenchloride In diethyl ether; ethanol; water at 0℃; |
4-Methoxybenzyl alcohol (280 g, 1780 mmol) dissolved in diethylether (400 mL) was added in drops to a mixture of diethylether (400 niL) and cone, hydrochloric acid (400 mL) over 2 h, and the mixture was stirred for 1 h. The organic layer was separated, and added to a solution prepared by dissolving L-cysteine (197 g, 1625 mmol) and 2N aqueous sodium hydroxide solution (980 mL) to ethanol (1890 mL).The mixture was stirred for 2 h at room temperature. After completion of the reaction, the reaction mixture was cooled to 0°C, and neutralized to pH 7 using 3N aqueous hydrochloric acid solution. The resulting solid was filtered and dried to give the title compound (250 g, Yield 64percent). |
64% | Stage #1: With hydrogenchloride In diethyl ether Stage #2: With sodium hydroxide In diethyl ether; ethanol; water at 20℃; for 2 h; Stage #3: With hydrogenchloride In diethyl ether; ethanol; water at 0℃; |
4-Methoxybenzyl alcohol (280 g, 1780 mmol) dissolved in diethylether (400 mL) was added in drops to a mixture of diethylether (400 mL) and conc. hydrochloric acid (400 mL) over 2 h, and the mixture was stirred for 1 h. The organic layer was separated, and added to a solution prepared by dissolving L-cysteine (197 g, 1625 mmol) and 2N aqueous sodium hydroxide solution (980 mL) to ethanol (1890 mL). The mixture was stirred for 2 h at room temperature. After completion of the reaction, the reaction mixture was cooled to 0°, and neutralized to pH 7 using 3N aqueous hydrochloric acid solution. The resulting solid was filtered and dried to give the title compound (250 g, Yield 64percent). |
64% | Stage #1: With hydrogenchloride In diethyl ether; water for 3 h; Stage #2: With sodium hydroxide In diethyl ether; ethanol; water at 20℃; for 2 h; Stage #3: With hydrogenchloride In diethyl ether; ethanol; water |
To a solvent mixture of diethylether (400 ml) and conc. hydrochloric acid (400 ml) was added in drops 4-methoxybenzylalcohol (280 g, 1780 mmol) dissolved in diethylether (400 ml) for 2 h, and the mixture was stirred for 1 h. The organic layer was separated, and added to a solution prepared by dissolving L-cysteine (197 g, 1625 mmol) and 2N aqueous sodium hydroxide solution (980 ml) in ethanol (1890 ml). The mixture was stirred for 2 h at room temperature. After completion of the reaction, the reaction solution was cooled to 0° C., and neutralized to pH 7 using 3N aqueous hydrochloric acid solution. The resulting solid was filtered, and dried to give (R)-2-amino-3-(4-methoxy-benzylsulfanyl)-propionic acid (250 g, 1035 mmol, Yield: 64percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | at 20℃; for 5 h; | To a solution of l-cysteine (1.0 g, 5.69 mmol) in acetic acid (15 mL) was added triphenyl methanol (1.64 g, 6.30 mmol), followed by adding trifluoroboron ethylether (720 μL, 5.69 mmol) dropwise and the reaction was stirred at room temperature. After 5 h, the reaction mixture was neutralized with saturated sodium acetate. The resulting precipitate was washed with ethylether and collected to give the desired compound 3 (1.87 g, 90percent) as a white solid. 1H NMR (300 MHz, acetone-d6): δ = 7.46-7.23 (m, 15H), 3.64 (dd, J = 8.10 Hz, 4.20 Hz, 1H), 2.67-2.52 (m, 2H). 13C NMR (75 MHz, DMSO-d6): δ = 169.89, 144.42, 129.25, 128.11, 126.78, 65.95, 53.64, 34.39. MALDI-TOF-MS: Calcd for C22H20NO2S 362.1. Found 362.1 [M-H]-. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With thionyl chloride In methanol for 3 h; Reflux; Inert atmosphere | General procedure: These compounds 11a-f were prepared using the generalmethod described by Gududuru et al. [35].Thionyl chloride (8.3 mL, 110 mmol) was added dropwise underan atmosphere of argon to a solution of L-cysteine (8) (9.00 g,74 mmol) in 150mL MeOH. The reaction mixture was refluxed for3 h then evaporated in vacuo, then co-evaporated with toluene(2 5 mL) to afford the hydrochloride salt of the methyl ester of Lcysteine(9) as white solid. One-sixth of this material (9)(12.4 mmol) was dissolved in water/ethanol (1:1) (15 mL). Sodiumhydrogen carbonate (1.14 g, 13.6 mmol) was added and, after10 min, the aromatic aldehyde (10a-f) (12.38 mmol) was added andthe reaction mixture was stirred for 14 h. The ethanol was evaporatedin vacuo and the aqueous residue was extracted with DCM(50 mL). The organic layer was washed with water (25 mL), driedover Na2SO4, filtered and evaporated in vacuo to afford the crudeproducts 11a-f. |
96% | at 0℃; for 2 h; Reflux | General procedure: Acetyl chloride (1.6 mL, 22 mmol) was added to MeOH (100 mL), and the solution was cooled to 0°C. The solution was stirred for 5 min. Amino acid (L-serine, D-serine, L-cysteine, D-cysteine, L-2,3-diaminopropionic acid, and D-2,3-diaminopropionic acid) (20 mmol) was then added to the acetyl chloride solution in methanol (MeOH), and the solution was heated to reflux for 2 h, then cooled to room temperature.The reaction was evaporated under reduced pressure and gavea colorless solid. The solid was washed with CH2Cl2 (20 mL)to give amino acid methyl ester hydrochloride (2d–f, 2d–f)as a white solid. The yields of 2d, d, e, e, f and f were 95percent,96percent, 94percent, 96percent, 95percent, 95percent, respectively. |
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