Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 312-84-5 | MDL No. : | MFCD00004269 |
Formula : | C3H7NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MTCFGRXMJLQNBG-UWTATZPHSA-N |
M.W : | 105.09 | Pubchem ID : | 71077 |
Synonyms : |
(R)-Serine;NSC 77689
|
Chemical Name : | H-D-Ser-OH |
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) : | 0.19 |
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 |
---|---|---|
95% | Stage #1: With sodium hydrogencarbonate In water at 0 - 5℃; Stage #2: at 0 - 20℃; |
A solution of NaHCO3 (605 g, 5.72 mol) in water(3 l) was cooled to 0–5°C on an ice bath, and D-serine (200 g, 1.90 mol) was added in portions (8–10 portions with 20–30 min interval). Then 50percent solution of benzyl chloroformate in toluene (780 g, 2.29 mol) at 0–5°C was added dropwise over a 1 h period. Reaction mixture was stirred for 2 h at 0–5°C, then warmed up to room temperature and stirred for 2 h more. Then EtOAc (400 ml) was added and pH adjusted to 2.0 with hydrochloric acid.Product was extracted with EtOAc (2×800 ml). Combined exstracts were concentrated under reduced pressure up to~640 ml affording a suspension. Cyclohexane (1200 ml) was added and resulting mixture slurried for 6 h. The purified product was isolated by filtration and dried under reduced pressure at 50°C to afford compound 2. Yield432.5 g (95percent), white solid, mp 119–120°C (mp 119°C27),[α]D25 –5.08 (c 2.7, AcOH). IR spectrum, ν, cm–1: 1689(C=O), 1749 (C=O), 3319 (NH), 3338 (OH). UV spectrum, λmax, nm: 208. 1H NMR spectrum (CD3OD), δ, ppm(J, Hz): 3.83–3.92 (2H, m, CH2); 4.30 (1H, t, J = 8.8,NCH); 5.13 (2H, s, CH2); 7.29–7.40 (5H, m, H Ph). 13C NMR spectrum (CD3OD), δ, ppm: 57.7; 63.1; 67.7;128.9 (2C); 129.0; 129.5 (2C); 138.1; 158.6; 173.8. Massspectrum, m/z (Irel,percent): 238 [M–H]– (100). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | at 20℃; for 24 h; Inert atmosphere | 4.2.1.1 (R)-Methyl 2-isopropyl-4,5-dihydrooxazole-4-carboxylate At first, SOCl2 (7.60 mL, 104.2 mmol) was added to d-serine (10.0 g, 95.1 mmol) in MeOH and allowed to react at room temperature for 24 h. 9a Removal of the solvents left a white solid that upon washing with n-hexane (3 * 25 mL) provided the d-serine methylester HCl salt (14.4 g, 97percent) as a colourless solid. 1H NMR (300 MHz, D2O) δ 4.32-4.28 (1H, m, CH), 4.12 (1H, dd, J 4.2, 12.5 Hz, CHaHbOH), 4.02 (1H, dd, J 3.4, 12.5 Hz, CHaHbOH), 3.88 (3H, s, CH3). |
96% | at 20℃; for 12 h; Inert atmosphere | Dichlorosulfoxide (18.68 g, 157.00 mmol) was slowly added dropwise to anhydrous salt-cooled anhydrous CH3OH (30 mL)under N2 protection. After the addition was completed, the reaction solution was warmed to room temperature and stirred for half an hour. Then, Compound 1 (5.00 g, 47.58 mmol) as described in the above reaction formula was added and reacted at room temperature for 12 hours, and the reaction solution became clear from turbidity. The reaction was concentrated and dried in vacuo to give a white solid: Compound 2 (7.10 g, 96percent). |
96% | at 5 - 20℃; for 4 h; | 10 g of D-serine and 40 ml of methanol were placed in a reaction flask, 10 ml of thionyl chloride was added dropwise at 5±2 ° C, and reacted at room temperature for 4 hours. After the reaction was completed, it was concentrated to dryness.The crude cycloserine ester hydrochloride salt was 14.00 g. |
95% | 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. |
93% | at -5 - 20℃; Inert atmosphere; Reflux; Green chemistry | Dissolve 105.09g D-serine in 1.5L dry methanol and cool down to -50°C.With nitrogen protection, 178.46 g of thionyl chloride was added dropwise, and after completion of the addition, the reaction was allowed to warm to room temperature and stirred for 2 hours.Then continue to heat up to reflux, stirring and refluxing overnight, after the reaction is complete, the solvent is evaporated under reduced pressure,Ethyl acetate was washed by washing with suction to obtain 219 g of white solid D-serine methyl ester hydrochloride in 93percent yield. |
67.75% | at 0 - 20℃; for 16 h; Inert atmosphere | To a stirred solution of D-serine (10 g, 95.23 mmol) in MeOH (100 mL) under an argon atmosphere was added thionylchloride (56.65 g, 476.19 mmol) at 0 oC. The reaction mixture was warmed to room temperature and stirred for 16 h. After consumption of the starting material (monitored by TLC), the volatile components were concentrated in vacuo. The crude material was washed with ether (2 x 100 mL) and dried in vacuo to obtain the methyl D-serinate hydrochloride (10 g, 67.75percent) as an off-white solid.1H-NMR (DMSO-d6, 500 MHz): δ 8.60-8.55 (m, 3H), 5.61-5.59 (m, 1H), 4.10-4.08 (m, 1H), 3.83-3.79 (m, 2H), 3.74 (s, 3H); TLC: 10percent MeOH/ CH2Cl2 (Rf: 0.3). |
67.75% | at 0 - 20℃; for 16 h; Inert atmosphere | Synthesis of methyl D-serinate hydrochloride To a stirred solution of D-serine (10 g, 95.23 mmol) in MeOH (100 mL) under an argon atmosphere was added thionylchloride (56.65 g, 476.19 mmol) at 0° C. The reaction mixture was warmed to room temperature and stirred for 16 h. After consumption of the starting material (monitored by TLC), the volatile components were concentrated in vacuo. The crude material was washed with ether (2*100 mL) and dried in vacuo to obtain the methyl D-serinate hydrochloride (10 g, 67.75percent) as an off-white solid. 1H-NMR (DMSO-d6, 500 MHz): δ 8.60-8.55 (m, 3H), 5.61-5.59 (m, 1H), 4.10-4.08 (m, 1H), 3.83-3.79 (m, 2H), 3.74 (s, 3H); TLC: 10percent MeOH/CH2Cl2 (Rf: 0.3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | for 15.5 h; Reflux | Example-1 Preparation of D-Serine Methyl Ester Hydrochloride D-serine (100 g, 0.9515 mole) was suspended in 600 ml methanol at room temperature. Acetyl chloride (224.0 g, 2.8545 mole) was added drop wise at -5° C. to 0° C. and stirred for 30 minutes. The reaction mixture was refluxed for 15 hours. Evaporation of the reaction mixture under reduced pressure followed by crystallization of the resulting residue from methanol and methyl tert-butyl ether, resulted in colorless solid of D-serine methyl ester hydrochloride (134.7 g, Yield: 91percent, HPLC: 99.6percent) M.R: 165−167° C. (Lit.: 163−165° C., Tetrahedron Letters, 2012, 53, 1668-1670,)[α]D20=3.7 (C=4 in EtOH); IR(KBr): 3361, 2921, 2660, 2732, 2550, 2488, 2134, 2079, 1922, 1747, 1592, 1505, 1471, 1444, 1431, 1382, 1343, 1297, 1258, 1187, 1158, 1128, 1094, 1038, 969, 900, 793, 844, 580, 469 Cm−1; H1NMR: (300 MHz, DMSO), δ3.745 (s, 3H), 3.82 (s, 2H), 4.11 (s, 1H), 5.63 (s, 1H), 8.58 (s, 2H); 13CNMR: (300 MHz, DMSO), δ 52.66, 54.37, 59.38, 161.39. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | Stage #1: for 0.0833333 h; Cooling with ice Stage #2: for 2 h; Reflux |
Acetyl chloride (4.06 mL, 57.14 mmol) was added to MeOH (100 mL) cooled in ice. The solution was stirred for 5 min. d-Serine (2 g, 19.04 ml) was added in one portion to a solution of d-serine in MeOH, and the solution was heated to reflux. The mixture was stirred for 2 h at reflux and cooled to room temperature. The reaction was evaporated under reduced pressure and gave a colorless solid. The solid was filtered and washed with CH2Cl2 (100 ml) to give d-serine methyl ester hydrochloride 2 (2.86 g, 97percent) as a white solid. mp 164-166 °C; -4 (c = 4.0, EtOH); 1H NMR (CD3OD, 300 MHz) δ 4.03 (m, 1H), 3.90 (dd, J = 6.6 Hz, J = 18.6 Hz, 1H), 3.82 (dd, J = 4.8 Hz, J = 17.4 Hz, 1H), 3.81 (s, 3H); 13C NMR (DMSO-d6, 75 MHz) δ 168.5, 59.5, 54.4, 52.8; HRMS (ESI) m/z (M+H)+ calculated for C4H10ClNO3 = 155.5801, found 155.4573. |
[ 6003-05-0 ]
(S)-2-Aminopropanoic acid hydrochloride
Similarity: 0.88