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CAS No. : | 56-45-1 | MDL No. : | MFCD00064224 |
Formula : | C3H7NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MTCFGRXMJLQNBG-REOHCLBHSA-N |
M.W : | 105.09 | Pubchem ID : | 5951 |
Synonyms : |
Serine;(S)-Serine
|
Chemical Name : | (S)-2-Amino-3-hydroxypropanoic acid |
Num. heavy atoms : | 7 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.67 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 22.18 |
TPSA : | 83.55 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) : | -9.12 cm/s |
Log Po/w (iLOGP) : | 0.18 |
Log Po/w (XLOGP3) : | -3.07 |
Log Po/w (WLOGP) : | -1.61 |
Log Po/w (MLOGP) : | -3.91 |
Log Po/w (SILICOS-IT) : | -1.45 |
Consensus Log Po/w : | -1.97 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 3.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 1.57 |
Solubility : | 3950.0 mg/ml ; 37.5 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 1.88 |
Solubility : | 7970.0 mg/ml ; 75.9 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | 1.3 |
Solubility : | 2080.0 mg/ml ; 19.8 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.51 |
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 |
---|---|---|
65% | Stage #1: With bromic acid; potassium bromide; sodium nitrite In water at -10 - 20℃; Stage #2: With bromic acid In water at 65℃; for 48 h; |
[1496] Step 2: methyl 2-bromo-3-hydroxypropanoate[1497] To a solution of L-serine (5.0 g, 47.6 mmol), a 48 w/wpercent bromic acid solution (13.0 mL, 109.5 mmol), and potassium bromide (20.0 g, 157.1 mmol) in water (44.0 mL) was added portionwise sodium nitrite (6.0 g, 80.9 mmol) at -10 ℃. The reaction mixture was stirred at room temperature overnight. The reaction mixture was saturated with sodium chloride and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated. The residue was dissolved in methanol (50.0 mL) and then 48 w/wpercent bromic acid (0.2 mL) was added thereto. The reaction mixture was stirred at 65 ℃ for 2 days and then concentrated under reduced pressure to discard excess methanol. The resulting dark yellow residue was dissolved in dichloromethane (100.0 mL) and then washed with a saturated sodium hydrogen carbonate solution (50.0 mL) and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and then evaporated. The residue was dried under reduced pressure to give 5.7 g of the titled compound (Yield: 65percent).[1498] 1H NMR (CDCl3, 400 MHz) δ 4.36(t, 1H), 4.01-4.08(m, 1H), 3.93-3.97(m, 1H), 3.82(s, 3H), 2.56(t, 1H) |
65% | Stage #1: With bromic acid; potassium bromide; sodium nitrite In water at -10 - 20℃; Stage #2: at 65℃; for 48 h; |
Step 2: methyl 2-bromo-3-hydroxypropanoate To a solution of L-serine (5.0 g, 47.6 mmol), a 48 w/w percent bromic acid solution (13.0 mL, 109.5 mmol), and potassium bromide (20.0 g, 157.1 mmol) in water (44.0 mL) was added portionwise sodium nitrite (6.0 g, 80.9 mmol) at -10° C. The reaction mixture was stirred at room temperature overnight. The reaction mixture was saturated with sodium chloride and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated. The residue was dissolved in methanol (50.0 mL) and then 48 w/w percent bromic acid (0.2 mL) was added thereto. The reaction mixture was stirred at 65° C. for 2 days and then concentrated under reduced pressure to discard excess methanol. The resulting dark yellow residue was dissolved in dichloromethane (100.0 mL) and then washed with a saturated sodium hydrogen carbonate solution (50.0 mL) and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and then evaporated. The residue was dried under reduced pressure to give 5.7 g of the titled compound (Yield: 65percent). 1H NMR (CDCl3, 400 MHz) δ 4.36 (t, 1H), 4.01-4.08 (m, 1H), 3.93-3.97 (m, 1H), 3.82 (s, 3H), 2.56 (t, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.4% | for 11 h; Cooling with ice; Reflux | In 100 ml of ethanol is added in three-mouth bottle 40 ml, under the condition of the mechanical stirring ice-water bath, slow adds by drops two chlorine Asia sulphone 5.4 ml, after dripping, continue to stir 1h, (II) 6.00g the L-serine (57mmol) inputs in three-mouth bottle, heating reflux reaction, the reaction time is 10h rear, reduced pressure distillation to remove the solvent, to obtain L-serine methyl ester hydrochloride (III) 9.05g, yield 93.4percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | Stage #1: With toluene-4-sulfonic acid In tetrachloromethaneReflux Stage #2: With hydrogenchloride In water |
a) A 250-mL flask was charged with H-l-Ser-OH (15) (15.00 g, 0.14 mol) and p-TsOH (29.30 g, 0.15 mol) in a mixture of BnOH (70 mL) and CCl4 (70 mL). The reaction mixture was heated at reflux under Dean-Stark conditions overnight (7 mL H2O removed). CCl4 was removed by evaporation under reduced pressure. DCM (50 mL) was added to the mixture and the resulting solution was washed with sat. NaHCO3 (3 x 50 mL). The organic phase was extracted with 1 M HCl (3 x 50 mL). The aqueous solution was concentration in vacuo and dried to yield H-Ser-OBn HCl (17.52 g, 54percent) as colorless crystals. mp 169-171 °C. LC-MS m/z: 196.15 [M+1].b) Boc-Phe-OH (2.92 g, 11.00 mmol) was dissolved in DMF (50 mL) in a 100-mL dry flask. DIPEA (1.88 mL, 11.00 mmol), EDCI (1.95 mL, 11.00 mmol), and HOBt (1.49 g, 11.00 mmol) were added to the reaction mixture. After the solution was stirred for 5 min at rt, H-Ser-OBn (2.31 g, 10.00 mmol) was added and stirring was continued overnight. The reaction mixture was diluted with 150 mL Et2O and washed with 1M HCl (2 x 100 mL), brine (100 mL), sat. NaHCO3 (2 x 100 mL), and brine (100 mL). The organic phase was dried over anhydrous MgSO4 and concentrated in vacuo. Flash chromatography purification using a mobile phase of 1:1 EtOAc, hexane afforded 16 (2.08 g, 78percent) as a colorless oil. |
52.3% | Stage #1: for 12 h; Heating / reflux Stage #2: With sodium hydrogencarbonate In water Stage #3: With hydrogenchloride In dichloromethane at 0℃; for 1.5 h; |
To prepare L-Serine benzyl ester hydrichloride sale (2), L-Serine (5.25 g) and p- toluenesulfonic acid (0.6 g) were suspended in benzyl alcohol (25 mL) and dissolved by heating on an oil bath using the Dean and Stark apparatus. Benzene (25 mL) was added and refluxed for 12 h; the reaction was cooled to RT and concentrated. The sample was then redissolved in 5percent NaHCO3 solution and extracted with i-PrOH/CHCl3 (1:4, 3x50 mL), dried over MgSO4, filtered and evaporated to a residue. The residue was dissolved in 125 mL of CH2Cl2 and HCl gas bubbled into the solution at O0C for 30 minutes followed by stirring for 1 h. The precipitated white solid was washed with diethyl ether and recrystallized from i-PrOH/CH3OH (13:1) according to the procedure of Holden et al. (2002) J. Org. Chem. 67, 5913-5918. Yield 52.3percent (over two steps), m.p. = 170-1710C, [a]233D = -4.35° (c = 1.1), 1H NMR (DMSO, 500 MHz) d 3.87 (d, J= 3 Hz, 2H), 4.14 (t, J= 3 Hz, IH), 5.21 ( s, 2H), 5.70 (IH, broad), 7.36 (m, 5H); 13C NMR (DMSO, 500 MHz) d 54.55 (β-CH2), 59.54 (a-CH), 66.90 (CH2Ph), 127.90 (CH), 128.19 (2CH), 128.42 (2CH), 135.31 (C, q), and 167.95 (-COO-). |
[ 6003-05-0 ]
(S)-2-Aminopropanoic acid hydrochloride
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