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[ CAS No. 26348-70-9 ] {[proInfo.proName]}

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Chemical Structure| 26348-70-9
Chemical Structure| 26348-70-9
Structure of 26348-70-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 26348-70-9 ]

CAS No. :26348-70-9 MDL No. :MFCD00039067
Formula : C7H18Cl2N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :SXZCBVCQHOJXDR-ILKKLZGPSA-N
M.W : 233.14 Pubchem ID :117778
Synonyms :
H-Lys-OMe.2HCl

Calculated chemistry of [ 26348-70-9 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.86
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 56.39
TPSA : 78.34 Ų

Pharmacokinetics

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) : -7.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.97
Log Po/w (WLOGP) : 1.22
Log Po/w (MLOGP) : 0.55
Log Po/w (SILICOS-IT) : -0.18
Consensus Log Po/w : 0.51

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.5
Solubility : 7.36 mg/ml ; 0.0316 mol/l
Class : Very soluble
Log S (Ali) : -2.2
Solubility : 1.46 mg/ml ; 0.00627 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.9
Solubility : 29.7 mg/ml ; 0.127 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.14

Safety of [ 26348-70-9 ]

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:

Application In Synthesis of [ 26348-70-9 ]

* 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.

  • Downstream synthetic route of [ 26348-70-9 ]

[ 26348-70-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 67-56-1 ]
  • [ 657-27-2 ]
  • [ 13515-95-2 ]
YieldReaction ConditionsOperation in experiment
100% With thionyl chloride; for 17h;Reflux; Into a flask were added L-lysine hydrochloride (2, 5.00 g, 27.4 mmol, 1 equiv) and methanol (30 mL, 0.9 M). The suspension was heated to reflux (dissolving the solid). Thionyl chloride (2.59 mL, 35.6 mmol, 1.3 equiv) was added dropwise (over 15 min). The reaction was maintained at reflux (17 h). Most of the volatiles were removed by distillation (approximately 25 mL), and the remaining volatiles were removed under reduced pressure (toluene azeotrope) to yield pure lysine methyl ester dihydrochloride (3, quantitative mass recovery, white solid), which was used directly in the next step. Compound analysis is consistent with published data. 1
97% With thionyl chloride; at 0℃;Reflux; Inert atmosphere; L-Lysine hydrochloride (100.0 g, 547 mmol) dissolved inMeOH (1200 mL) was stirred for 30 min at 0 C under Ar. Thionyl chloride (80 mL, 1.10 mol) was addeddropwise over 20 min at 0 C. The solution was stirred for 1 h at room temperature, and refluxed forovernight. After removal of the solvent in vacuo, the crude product was recrystallized from MeOH to givemethyl L-lysinate dihydrochloride (124.1 g, yield 97percent). Methyl L-lysinate dihydrochloride (60.0 g, 257mmol) dissolved in MeOH (1200 mL) was stirred at room temperature under Ar. NaOMe (48.0 g, 889mmol) was added, and the solution was refluxed for 4 h. The mixture was hydrolyzed by addingammonium chloride (20.0 g), and the solution was filtered, and then the solvent was removed in vacuo.The residue was dissolved in dimethoxyethane (80 mL), and the solution was filtered, and then thesolvent was removed in vacuo. The residue was dissolved in EtOH (100 mL), and EtOH saturated withHCl (20 mL) was added to give the crude product. The crude product was recrystallized from MeOH togive (S)-3-aminozepan-2-one hydrochloride (5: 27.8 g, yield 66percent)
96% With thionyl chloride; In methanol; at 0℃;Reflux; Lysine hydrochloride (2 g, 10.95 mmol) was weighed into a roundbottom flask together with 80 mL methanol. The resulting suspension was then cooled to 0 °C on ice,before dropwise addition of thionyl chloride 8 mL (110 mmol). Upon addition the reaction mixtureturned homogenous. Subsequently, the flask was fitted with a reflux condenser and heated to refluxovernight. After allowing the mixture to reach room temperature, the solvent was removed underreduced pressure. The crude solid was then placed under high vacuum overnight to afford lysinemethyl ester dihydrochloride as a white solid (2.3 g, 9.83 mmol, 96percent).
91.6% With hydrogenchloride; In methanol; at 0℃; for 7h; Example-1 L-Lysine methyl ester dihydrochloride To a mixture of L-lysine HCl (100 grams, 547.49 mmol) in methanol (1.75 lit) at 0° C. was bubbled dry HCl for 7 hours. The crude solid product was filtered, dried to get pure 1 (117 grams, 91.6percent) as a white powder. M.p: 204.5-206° C. (lit 213-215° C.). 1H NMR (DMSO-d6) delta 1.48 (m, 2H, CH2), 1.68 (m, 2H, CH2), 1.90 (m, 2H, CH2), 2.80 (m, 2H, CH2), 3.78 (s, 3H, Ester), 4.00 (t, 1H, CH), 8.20 (Bs, 2H, NH2), 8.70 (Bs, 2H, NH2).
With thionyl chloride; Amino Acid Derivatives; In order to synthesize iminosugar-amino acid conjugates that contain just one single amino acid residue, different L-lysine and L-serine derivatives have to be prepared, following standard procedures (see Figure 13). Commercially available H-L-Lys(Boc)-OMe hydrochloride 41 can be used directly for reductive amination of the Nepsilon-amino function. Selective reaction of the Nepsilon-amino functionality can be achieved by the use of Boc-L-Lys(Z)-OMe 45, which can be prepared from Boc-L-Lys(Z)-OH 44 by simple treatment with TBTU and triethylamine in methanol at ambient temperature. For simultaneous reaction of both amino functions, L-lysine methyl ester dihydrochloride 43 can be used in the reductive amination process. Reaction of L-lysine hydrochloride 42 with SOCl2 in dry methanol furnishes the corresponding methyl ester dihydrochloride 43 in high yield. Although commercially available L-serine methyl ester hydrochloride 46 could be directly employed, Z-L-Ser-OMe 47 is prepared by treatment of 46 with benzyl chloroformate in pure DMF in the presence of triethylamine. Compound 47 is very easy to handle in the reductive amination process, since the addition of base is not necessary to deprotonate the hydrochloride, as it would be necessary for 46.

  • 2
  • [ 67-56-1 ]
  • [ 56-87-1 ]
  • [ 13515-95-2 ]
YieldReaction ConditionsOperation in experiment
100% Methanol (50 mL) was cooled down to 0 °C and thionyl chloride (100 mmol, 7.25 mL) was added dropwise. After stirring for ten minutes (S)-lysine (50.9 mmol, 7.31 g) was added portionwise and the reaction mixture was stirred for further ten minutes at 0 °C. Afterwards the mixture was heated to reflux for three hours. The reaction mixture was cooled down to room temperature and the solvent was removed under reduced pressure. After drying under vacuum (S)-lysine methyl ester dihydrochloride (50.9 mmol, 11.9 g, quant.) was obtained as white solid.1H-NMR (600 MHz, D2O): delta (ppm) = 1.27-1.41 (m, 2 H), 1.60 (td, J = 7.2 Hz,J = 15.5 Hz, 2 H), 1.75-1.81 (m, 1 H), 1.84-1.90 (m, 1 H), 2.84 (t, J = 7.7 Hz,2 H), 3.68 (s, 3 H), 4.00 (t, J = 6.5 Hz, 1 H).13C-NMR (91 MHz, D2O): delta (ppm) = 22.1 (CH2), 26.9 (CH2), 29.9 (CH2), 39.7 (CH2),53.3 (CH3), 54.2 (CH), 171.2 (Cq).
87% With hydrogenchloride; L-lysine (a) (14.60 g, 100 mmol) was dissolved in 150 mL of MeOH, anhydrous HCl gas was added until the solution changed from clarification to turbidity. Then, the solvent was evaporated with the desired compound b (17.10 g, 87 percent yield) being recrystallized as white solid by ester. Mp: 200-203 °C.
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