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[ CAS No. 598-55-0 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 598-55-0
Chemical Structure| 598-55-0
Chemical Structure| 598-55-0
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Product Details of [ 598-55-0 ]

CAS No. :598-55-0 MDL No. :MFCD00007964
Formula : C2H5NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :GTCAXTIRRLKXRU-UHFFFAOYSA-N
M.W : 75.07 Pubchem ID :11722
Synonyms :

Calculated chemistry of [ 598-55-0 ]

Physicochemical Properties

Num. heavy atoms : 5
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 16.11
TPSA : 52.32 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) : -7.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.91
Log Po/w (XLOGP3) : -0.66
Log Po/w (WLOGP) : -0.29
Log Po/w (MLOGP) : -0.96
Log Po/w (SILICOS-IT) : -0.9
Consensus Log Po/w : -0.38

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.18
Solubility : 113.0 mg/ml ; 1.5 mol/l
Class : Highly soluble
Log S (Ali) : 0.03
Solubility : 81.4 mg/ml ; 1.08 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.53
Solubility : 257.0 mg/ml ; 3.42 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.18

Safety of [ 598-55-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P201-P202-P264-P280-P305+P351+P338-P312-P337+P313-P405-P501 UN#:N/A
Hazard Statements:H302+H312-H319-H351 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 598-55-0 ]

* 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.

  • Upstream synthesis route of [ 598-55-0 ]
  • Downstream synthetic route of [ 598-55-0 ]

[ 598-55-0 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 66766-07-2 ]
  • [ 598-55-0 ]
  • [ 1665-48-1 ]
YieldReaction ConditionsOperation in experiment
92% at 145 - 150℃; for 10 h; Example 1 :; 50 g (0.2564 mol) of 3-(3,5-dimethylphenoxy)-l-amino-2-propanol was reacted at 145°C- 1500C for 10 hours with 25.0 g (0.333 mol) of methyl carbamate in the presence of 0.005- 0.006 mol of base (LiNH2, methanolic solution of NaOCH3, NaOH, or KOH). The completion of the reaction is checked by HPLC. The hot reaction mixture was treated with 100 mL of water and 150 mL of butyl acetate. The pH of the mixture was adjusted to 5 with acetic acid. Two layers were separated at 80°C-90°C. The residual water in the organic layer is separated by distillation. Upon cooling, the organic phase separated metaxalone crude at 70percent-72percent yield. The crude metaxalone is purified by crystallization from a carbon treated butyl acetate solution. Yield: 92percent-95percentFurther experiments concerning the reaction parameters have shown that: a. the reaction time is solely a function of temperature; b. the amount of 3-(3,5-dimethylphenoxy)-l-amino-2-propanol residual (unreacted) starting material is also a function of temperature; c. the concentration of the impurities is a function of both temperature and methyl carbamate stoichiometry, where lower temperatures and lower mole ratios of methyl carbamate to 3-(3,5-dimethylphenoxy)-l-amino-2-propanol minimize the impurities formation; and d. the yield is increased at lower mole ratios of methyl carbamate to 3 -(3, 5- dimethylphenoxy)-l-amino-2-propanol and at higher temperatures. <n="5"/>In summary, the reaction should be run at the lower temperature in order to minimize the formation of impurities and lower molar ratio of methyl carbamate to 3 -(3, 5- dimethylphenoxy)-l-amino-2-propanol is preferable.
92% at 145 - 150℃; for 10 h; Example 1 :; 50 g (0.2564 mol) of 3-(3,5-dimethylphenoxy)-l-amino-2-propanol was reacted at 145°C- 1500C for 10 hours with 25.0 g (0.333 mol) of methyl carbamate in the presence of 0.005- 0.006 mol of base (LiNH2, methanolic solution of NaOCH3, NaOH, or KOH). The completion of the reaction is checked by HPLC. The hot reaction mixture was treated with 100 mL of water and 150 mL of butyl acetate. The pH of the mixture was adjusted to 5 with acetic acid. Two layers were separated at 80°C-90°C. The residual water in the organic layer is separated by distillation. Upon cooling, the organic phase separated metaxalone crude at 70percent-72percent yield. The crude metaxalone is purified by crystallization from a carbon treated butyl acetate solution. Yield: 92percent-95percentFurther experiments concerning the reaction parameters have shown that: a. the reaction time is solely a function of temperature; b. the amount of 3-(3,5-dimethylphenoxy)-l-amino-2-propanol residual (unreacted) starting material is also a function of temperature; c. the concentration of the impurities is a function of both temperature and methyl carbamate stoichiometry, where lower temperatures and lower mole ratios of methyl carbamate to 3-(3,5-dimethylphenoxy)-l-amino-2-propanol minimize the impurities formation; and d. the yield is increased at lower mole ratios of methyl carbamate to 3 -(3, 5- dimethylphenoxy)-l-amino-2-propanol and at higher temperatures. <n="5"/>In summary, the reaction should be run at the lower temperature in order to minimize the formation of impurities and lower molar ratio of methyl carbamate to 3 -(3, 5- dimethylphenoxy)-l-amino-2-propanol is preferable.
91.3% at 145 - 150℃; for 10 - 14 h; Example 1 :; 50 g (0.2564 mol) of 3-(3,5-dimethylphenoxy)-l-amino-2-propanol was reacted at 145°C- 1500C for 10 hours with 25.0 g (0.333 mol) of methyl carbamate in the presence of 0.005- 0.006 mol of base (LiNH2, methanolic solution of NaOCH3, NaOH, or KOH). The completion of the reaction is checked by HPLC. The hot reaction mixture was treated with 100 mL of water and 150 mL of butyl acetate. The pH of the mixture was adjusted to 5 with acetic acid. Two layers were separated at 80°C-90°C. The residual water in the organic layer is separated by distillation. Upon cooling, the organic phase separated metaxalone crude at 70percent-72percent yield. The crude metaxalone is purified by crystallization from a carbon treated butyl acetate solution. Yield: 92percent-95percentFurther experiments concerning the reaction parameters have shown that: a. the reaction time is solely a function of temperature; b. the amount of 3-(3,5-dimethylphenoxy)-l-amino-2-propanol residual (unreacted) starting material is also a function of temperature; c. the concentration of the impurities is a function of both temperature and methyl carbamate stoichiometry, where lower temperatures and lower mole ratios of methyl carbamate to 3-(3,5-dimethylphenoxy)-l-amino-2-propanol minimize the impurities formation; and d. the yield is increased at lower mole ratios of methyl carbamate to 3 -(3, 5- dimethylphenoxy)-l-amino-2-propanol and at higher temperatures. <n="5"/>In summary, the reaction should be run at the lower temperature in order to minimize the formation of impurities and lower molar ratio of methyl carbamate to 3 -(3, 5- dimethylphenoxy)-l-amino-2-propanol is preferable.; Example 2:; The methyl carbamate stoichiometry is determinant for the formation of the major impurity. The limit of diminishing returns has been demonstrated to be at 1.25-1.35 equivalents of methyl carbamate. As shown in Table 1, the data also show that LiNH2 or CH3ONa can be used interchangeably. <n="6"/> <n="7"/>The 3-(3,5-dimethylphenoxy)-l-amino-2-propanol starting material has to be of good quality including chemical purity and color. Colored impurities are only partially removed by the butyl acetate treatment and impact the quality of the final product with respect to color. Accordingly, it is advantageous for carbon treatment to be applied either to the crude or to the final purification step.In addition, the filtrate from the final purification can be recycled in part. Unreacted 3-(3,5- dimethylphenoxy)-l-amino-2-propanol can be separated from the concentrated filtrates and can be recycled after separation by filtration and drying. A better alternative would be to run the reaction as close to completion as practical.
90.7% at 145 - 150℃; for 5.5 - 10 h; Example 1 :; 50 g (0.2564 mol) of 3-(3,5-dimethylphenoxy)-l-amino-2-propanol was reacted at 145°C- 1500C for 10 hours with 25.0 g (0.333 mol) of methyl carbamate in the presence of 0.005- 0.006 mol of base (LiNH2, methanolic solution of NaOCH3, NaOH, or KOH). The completion of the reaction is checked by HPLC. The hot reaction mixture was treated with 100 mL of water and 150 mL of butyl acetate. The pH of the mixture was adjusted to 5 with acetic acid. Two layers were separated at 80°C-90°C. The residual water in the organic layer is separated by distillation. Upon cooling, the organic phase separated metaxalone crude at 70percent-72percent yield. The crude metaxalone is purified by crystallization from a carbon treated butyl acetate solution. Yield: 92percent-95percentFurther experiments concerning the reaction parameters have shown that: a. the reaction time is solely a function of temperature; b. the amount of 3-(3,5-dimethylphenoxy)-l-amino-2-propanol residual (unreacted) starting material is also a function of temperature; c. the concentration of the impurities is a function of both temperature and methyl carbamate stoichiometry, where lower temperatures and lower mole ratios of methyl carbamate to 3-(3,5-dimethylphenoxy)-l-amino-2-propanol minimize the impurities formation; and d. the yield is increased at lower mole ratios of methyl carbamate to 3 -(3, 5- dimethylphenoxy)-l-amino-2-propanol and at higher temperatures. <n="5"/>In summary, the reaction should be run at the lower temperature in order to minimize the formation of impurities and lower molar ratio of methyl carbamate to 3 -(3, 5- dimethylphenoxy)-l-amino-2-propanol is preferable.; Example 2:; The methyl carbamate stoichiometry is determinant for the formation of the major impurity. The limit of diminishing returns has been demonstrated to be at 1.25-1.35 equivalents of methyl carbamate. As shown in Table 1, the data also show that LiNH2 or CH3ONa can be used interchangeably. <n="6"/> <n="7"/>The 3-(3,5-dimethylphenoxy)-l-amino-2-propanol starting material has to be of good quality including chemical purity and color. Colored impurities are only partially removed by the butyl acetate treatment and impact the quality of the final product with respect to color. Accordingly, it is advantageous for carbon treatment to be applied either to the crude or to the final purification step.In addition, the filtrate from the final purification can be recycled in part. Unreacted 3-(3,5- dimethylphenoxy)-l-amino-2-propanol can be separated from the concentrated filtrates and can be recycled after separation by filtration and drying. A better alternative would be to run the reaction as close to completion as practical.

Reference: [1] Patent: WO2008/6096, 2008, A1, . Location in patent: Page/Page column 2-4
[2] Patent: WO2008/6096, 2008, A1, . Location in patent: Page/Page column 2-4
[3] Patent: WO2008/6096, 2008, A1, . Location in patent: Page/Page column 2-6
[4] Patent: WO2008/6096, 2008, A1, . Location in patent: Page/Page column 2-6
  • 2
  • [ 598-55-0 ]
  • [ 298-12-4 ]
  • [ 110599-27-4 ]
Reference: [1] Tetrahedron, 1987, vol. 43, # 2, p. 439 - 450
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