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[ CAS No. 5545-52-8 ] {[proInfo.proName]}

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Chemical Structure| 5545-52-8
Chemical Structure| 5545-52-8
Structure of 5545-52-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 5545-52-8 ]

CAS No. :5545-52-8 MDL No. :MFCD00042857
Formula : C16H21NO6 Boiling Point : -
Linear Structure Formula :- InChI Key :HLSLRFBLVZUVIE-LBPRGKRZSA-N
M.W : 323.34 Pubchem ID :111082
Synonyms :

Calculated chemistry of [ 5545-52-8 ]

Physicochemical Properties

Num. heavy atoms : 23
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.44
Num. rotatable bonds : 10
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 82.24
TPSA : 101.93 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.6
Log Po/w (XLOGP3) : 1.88
Log Po/w (WLOGP) : 1.95
Log Po/w (MLOGP) : 1.59
Log Po/w (SILICOS-IT) : 1.58
Consensus Log Po/w : 1.92

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.56
Solubility : 0.886 mg/ml ; 0.00274 mol/l
Class : Soluble
Log S (Ali) : -3.64
Solubility : 0.0736 mg/ml ; 0.000228 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.25
Solubility : 0.183 mg/ml ; 0.000566 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.4

Safety of [ 5545-52-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P272-P280-P302+P352-P304+P340+P312-P305+P351+P338-P333+P313-P337+P313-P362+P364-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H317-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5545-52-8 ]

* 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 [ 5545-52-8 ]
  • Downstream synthetic route of [ 5545-52-8 ]

[ 5545-52-8 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 5545-52-8 ]
  • [ 1676-90-0 ]
Reference: [1] Tetrahedron, 1972, vol. 28, p. 2649 - 2654
[2] Chemische Berichte, 1972, vol. 105, # 11, p. 3650 - 3657
  • 2
  • [ 63327-57-1 ]
  • [ 5545-52-8 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 23, p. 2719 - 2721
[2] Synthetic Communications, 1992, vol. 22, # 6, p. 883 - 891
[3] Gazzetta Chimica Italiana, 1964, vol. 94, p. 695 - 709
  • 3
  • [ 23632-69-1 ]
  • [ 5545-52-8 ]
Reference: [1] Tetrahedron Letters, 1993, vol. 34, # 46, p. 7409 - 7412
  • 4
  • [ 540-88-5 ]
  • [ 1152-61-0 ]
  • [ 47307-26-6 ]
  • [ 5545-52-8 ]
  • [ 42417-76-5 ]
YieldReaction ConditionsOperation in experiment
48.9 %Chromat. at 20℃; for 5.5 h; The transesterication reactions were set up in the same manner as described in EXAMPLE 1. However, in place of BF3.Et2O, an alternative catalyst was used. The catalysts tested were acids or salts, as listed in TABLE I below. Each reaction was run at room temperature or at about 50 C., for a period of about 5.5 to 15 hours. At the end of the reaction time, the reaction mixture was analyzed using the HPLC technique, as described in EXAMPLE 1. The results in TABLE I show that the transesterification reactions in the presence of certain catalysts, namely, concentrated sulfuric acid (H2SO4), methanesulfonic acid (MsOH), zinc chloride (ZnCl2) and titanium tetrachloride in dichloromethane (TiCl4 in DCM), yielded significant amounts of the Z-Asp(OtBu)2. In contrary, aluminum chloride (AlCl3), ferric chloride (FeCl3) and titanium tetraisopropoxide (Ti [ OiPr]4) were not as effective, even with the increase in the reaction temperature and the reaction time.
0 - 0.17 %Chromat. at 20 - 50℃; for 5.5 - 15 h; The transesterication reactions were set up in the same manner as described in EXAMPLE 1. However, in place of BF3.Et2O, an alternative catalyst was used. The catalysts tested were acids or salts, as listed in TABLE I below. Each reaction was run at room temperature or at about 50 C., for a period of about 5.5 to 15 hours. At the end of the reaction time, the reaction mixture was analyzed using the HPLC technique, as described in EXAMPLE 1. The results in TABLE I show that the transesterification reactions in the presence of certain catalysts, namely, concentrated sulfuric acid (H2SO4), methanesulfonic acid (MsOH), zinc chloride (ZnCl2) and titanium tetrachloride in dichloromethane (TiCl4 in DCM), yielded significant amounts of the Z-Asp(OtBu)2. In contrary, aluminum chloride (AlCl3), ferric chloride (FeCl3) and titanium tetraisopropoxide (Ti [ OiPr]4) were not as effective, even with the increase in the reaction temperature and the reaction time.
1.44 - 1.78 %Chromat. at 20 - 50℃; for 5.5 - 15 h; The transesterication reactions were set up in the same manner as described in EXAMPLE 1. However, in place of BF3.Et2O, an alternative catalyst was used. The catalysts tested were acids or salts, as listed in TABLE I below. Each reaction was run at room temperature or at about 50 C., for a period of about 5.5 to 15 hours. At the end of the reaction time, the reaction mixture was analyzed using the HPLC technique, as described in EXAMPLE 1. The results in TABLE I show that the transesterification reactions in the presence of certain catalysts, namely, concentrated sulfuric acid (H2SO4), methanesulfonic acid (MsOH), zinc chloride (ZnCl2) and titanium tetrachloride in dichloromethane (TiCl4 in DCM), yielded significant amounts of the Z-Asp(OtBu)2. In contrary, aluminum chloride (AlCl3), ferric chloride (FeCl3) and titanium tetraisopropoxide (Ti [ OiPr]4) were not as effective, even with the increase in the reaction temperature and the reaction time.
48.55 %Chromat. at 20℃; for 6.5 h; The transesterication reactions were set up in the same manner as described in EXAMPLE 1. However, in place of BF3.Et2O, an alternative catalyst was used. The catalysts tested were acids or salts, as listed in TABLE I below. Each reaction was run at room temperature or at about 50 C., for a period of about 5.5 to 15 hours. At the end of the reaction time, the reaction mixture was analyzed using the HPLC technique, as described in EXAMPLE 1. The results in TABLE I show that the transesterification reactions in the presence of certain catalysts, namely, concentrated sulfuric acid (H2SO4), methanesulfonic acid (MsOH), zinc chloride (ZnCl2) and titanium tetrachloride in dichloromethane (TiCl4 in DCM), yielded significant amounts of the Z-Asp(OtBu)2. In contrary, aluminum chloride (AlCl3), ferric chloride (FeCl3) and titanium tetraisopropoxide (Ti [ OiPr]4) were not as effective, even with the increase in the reaction temperature and the reaction time.
0 - 19.01 %Chromat. at 20 - 50℃; for 6.5 - 15 h; The transesterication reactions were set up in the same manner as described in EXAMPLE 1. However, in place of BF3.Et2O, an alternative catalyst was used. The catalysts tested were acids or salts, as listed in TABLE I below. Each reaction was run at room temperature or at about 50 C., for a period of about 5.5 to 15 hours. At the end of the reaction time, the reaction mixture was analyzed using the HPLC technique, as described in EXAMPLE 1. The results in TABLE I show that the transesterification reactions in the presence of certain catalysts, namely, concentrated sulfuric acid (H2SO4), methanesulfonic acid (MsOH), zinc chloride (ZnCl2) and titanium tetrachloride in dichloromethane (TiCl4 in DCM), yielded significant amounts of the Z-Asp(OtBu)2. In contrary, aluminum chloride (AlCl3), ferric chloride (FeCl3) and titanium tetraisopropoxide (Ti [ OiPr]4) were not as effective, even with the increase in the reaction temperature and the reaction time.
1.63 - 4.09 %Chromat. at 20 - 50℃; for 5.5 - 15 h; The transesterication reactions were set up in the same manner as described in EXAMPLE 1. However, in place of BF3.Et2O, an alternative catalyst was used. The catalysts tested were acids or salts, as listed in TABLE I below. Each reaction was run at room temperature or at about 50 C., for a period of about 5.5 to 15 hours. At the end of the reaction time, the reaction mixture was analyzed using the HPLC technique, as described in EXAMPLE 1. The results in TABLE I show that the transesterification reactions in the presence of certain catalysts, namely, concentrated sulfuric acid (H2SO4), methanesulfonic acid (MsOH), zinc chloride (ZnCl2) and titanium tetrachloride in dichloromethane (TiCl4 in DCM), yielded significant amounts of the Z-Asp(OtBu)2. In contrary, aluminum chloride (AlCl3), ferric chloride (FeCl3) and titanium tetraisopropoxide (Ti [ OiPr]4) were not as effective, even with the increase in the reaction temperature and the reaction time.
0.18 - 0.45 %Chromat. at 20 - 50℃; for 6.5 - 15 h; The transesterication reactions were set up in the same manner as described in EXAMPLE 1. However, in place of BF3.Et2O, an alternative catalyst was used. The catalysts tested were acids or salts, as listed in TABLE I below. Each reaction was run at room temperature or at about 50 C., for a period of about 5.5 to 15 hours. At the end of the reaction time, the reaction mixture was analyzed using the HPLC technique, as described in EXAMPLE 1. The results in TABLE I show that the transesterification reactions in the presence of certain catalysts, namely, concentrated sulfuric acid (H2SO4), methanesulfonic acid (MsOH), zinc chloride (ZnCl2) and titanium tetrachloride in dichloromethane (TiCl4 in DCM), yielded significant amounts of the Z-Asp(OtBu)2. In contrary, aluminum chloride (AlCl3), ferric chloride (FeCl3) and titanium tetraisopropoxide (Ti [ OiPr]4) were not as effective, even with the increase in the reaction temperature and the reaction time.

Reference: [1] Patent: US2003/236430, 2003, A1, . Location in patent: Page 3
[2] Patent: US2003/236430, 2003, A1, . Location in patent: Page 3
[3] Patent: US2003/236430, 2003, A1, . Location in patent: Page 3
[4] Patent: US2003/236430, 2003, A1, . Location in patent: Page 3
[5] Patent: US2003/236430, 2003, A1, . Location in patent: Page 3
[6] Patent: US2003/236430, 2003, A1, . Location in patent: Page 3
[7] Patent: US2003/236430, 2003, A1, . Location in patent: Page 3
  • 5
  • [ 2131-29-5 ]
  • [ 5545-52-8 ]
Reference: [1] Journal of Organic Chemistry, 1963, vol. 28, p. 1251 - 1253
  • 6
  • [ 57933-83-2 ]
  • [ 1152-61-0 ]
  • [ 75-65-0 ]
  • [ 47307-26-6 ]
  • [ 5545-52-8 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 15, p. 1665 - 1668
  • 7
  • [ 540-88-5 ]
  • [ 1152-61-0 ]
  • [ 47307-26-6 ]
  • [ 5545-52-8 ]
Reference: [1] Patent: US2003/236430, 2003, A1, . Location in patent: Page 3
  • 8
  • [ 774-65-2 ]
  • [ 1152-61-0 ]
  • [ 47307-26-6 ]
  • [ 5545-52-8 ]
YieldReaction ConditionsOperation in experiment
68.56 %Chromat. at 20℃; for 5 h; The transesterification reactions were set up in the same manner described in EXAMPLE 1. However, in place of tert-butyl acetate, an alternative tert-butyl compound was added to the starting material (Z-L-Asp). The tert-butyl compounds tested were in the form of solvents. Each reaction was run at room temperature for about 4.5 to 5 hours. At the end of the reaction time, each mixture was analyzed using the UPLC technique, as described in EXAMPLE 1. The results in TABLE II show that the transesterification reactions in the presence of certain tert-butyl compounds, namely, tert-butyl benzoate, tert-butyl methacrylate, tert butyl propionate, and tert-butyl bromoacetate, yielded significant amounts of Z-Asp(OtBu)2. In contrary, methyl-tert butyl ether (MTBE), and tert-butyl formate were not as effective for producing Z-Asp(OtBu)2.
Reference: [1] Patent: US2003/236430, 2003, A1, . Location in patent: Page column 4
  • 9
  • [ 23632-66-8 ]
  • [ 5545-52-8 ]
Reference: [1] Tetrahedron Letters, 1993, vol. 34, # 46, p. 7409 - 7412
  • 10
  • [ 4515-23-5 ]
  • [ 5545-52-8 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1964, vol. 673, p. 208 - 220
[2] Chemische Berichte, 1972, vol. 105, # 11, p. 3650 - 3657
  • 11
  • [ 762-75-4 ]
  • [ 1152-61-0 ]
  • [ 47307-26-6 ]
  • [ 5545-52-8 ]
  • [ 42417-76-5 ]
YieldReaction ConditionsOperation in experiment
2.24 %Chromat. at 20℃; for 5 h; The transesterification reactions were set up in the same manner described in EXAMPLE 1. However, in place of tert-butyl acetate, an alternative tert-butyl compound was added to the starting material (Z-L-Asp). The tert-butyl compounds tested were in the form of solvents. Each reaction was run at room temperature for about 4.5 to 5 hours. At the end of the reaction time, each mixture was analyzed using the UPLC technique, as described in EXAMPLE 1. The results in TABLE II show that the transesterification reactions in the presence of certain tert-butyl compounds, namely, tert-butyl benzoate, tert-butyl methacrylate, tert butyl propionate, and tert-butyl bromoacetate, yielded significant amounts of Z-Asp(OtBu)2. In contrary, methyl-tert butyl ether (MTBE), and tert-butyl formate were not as effective for producing Z-Asp(OtBu)2.
Reference: [1] Patent: US2003/236430, 2003, A1, . Location in patent: Page column 4
  • 12
  • [ 5292-43-3 ]
  • [ 1152-61-0 ]
  • [ 47307-26-6 ]
  • [ 5545-52-8 ]
  • [ 42417-76-5 ]
YieldReaction ConditionsOperation in experiment
29.58 %Chromat. at 20℃; for 4.5 h; The transesterification reactions were set up in the same manner described in EXAMPLE 1. However, in place of tert-butyl acetate, an alternative tert-butyl compound was added to the starting material (Z-L-Asp). The tert-butyl compounds tested were in the form of solvents. Each reaction was run at room temperature for about 4.5 to 5 hours. At the end of the reaction time, each mixture was analyzed using the UPLC technique, as described in EXAMPLE 1. The results in TABLE II show that the transesterification reactions in the presence of certain tert-butyl compounds, namely, tert-butyl benzoate, tert-butyl methacrylate, tert butyl propionate, and tert-butyl bromoacetate, yielded significant amounts of Z-Asp(OtBu)2. In contrary, methyl-tert butyl ether (MTBE), and tert-butyl formate were not as effective for producing Z-Asp(OtBu)2.
Reference: [1] Patent: US2003/236430, 2003, A1, . Location in patent: Page column 4
  • 13
  • [ 1634-04-4 ]
  • [ 1152-61-0 ]
  • [ 47307-26-6 ]
  • [ 5545-52-8 ]
  • [ 42417-76-5 ]
YieldReaction ConditionsOperation in experiment
0.99 - 2.15 %Chromat. at 20℃; for 4.5 - 48 h; The transesterification reactions were set up in the same manner described in EXAMPLE 1. However, in place of tert-butyl acetate, an alternative tert-butyl compound was added to the starting material (Z-L-Asp). The tert-butyl compounds tested were in the form of solvents. Each reaction was run at room temperature for about 4.5 to 5 hours. At the end of the reaction time, each mixture was analyzed using the UPLC technique, as described in EXAMPLE 1. The results in TABLE II show that the transesterification reactions in the presence of certain tert-butyl compounds, namely, tert-butyl benzoate, tert-butyl methacrylate, tert butyl propionate, and tert-butyl bromoacetate, yielded significant amounts of Z-Asp(OtBu)2. In contrary, methyl-tert butyl ether (MTBE), and tert-butyl formate were not as effective for producing Z-Asp(OtBu)2.
Reference: [1] Patent: US2003/236430, 2003, A1, . Location in patent: Page column 4
  • 14
  • [ 585-07-9 ]
  • [ 1152-61-0 ]
  • [ 47307-26-6 ]
  • [ 5545-52-8 ]
  • [ 42417-76-5 ]
YieldReaction ConditionsOperation in experiment
54.81 %Chromat. at 20℃; for 5 h; The transesterification reactions were set up in the same manner described in EXAMPLE 1. However, in place of tert-butyl acetate, an alternative tert-butyl compound was added to the starting material (Z-L-Asp). The tert-butyl compounds tested were in the form of solvents. Each reaction was run at room temperature for about 4.5 to 5 hours. At the end of the reaction time, each mixture was analyzed using the UPLC technique, as described in EXAMPLE 1. The results in TABLE II show that the transesterification reactions in the presence of certain tert-butyl compounds, namely, tert-butyl benzoate, tert-butyl methacrylate, tert butyl propionate, and tert-butyl bromoacetate, yielded significant amounts of Z-Asp(OtBu)2. In contrary, methyl-tert butyl ether (MTBE), and tert-butyl formate were not as effective for producing Z-Asp(OtBu)2.
Reference: [1] Patent: US2003/236430, 2003, A1, . Location in patent: Page column 4
  • 15
  • [ 20487-40-5 ]
  • [ 1152-61-0 ]
  • [ 47307-26-6 ]
  • [ 5545-52-8 ]
  • [ 42417-76-5 ]
YieldReaction ConditionsOperation in experiment
45.76 %Chromat. at 20℃; for 5 h; The transesterification reactions were set up in the same manner described in EXAMPLE 1. However, in place of tert-butyl acetate, an alternative tert-butyl compound was added to the starting material (Z-L-Asp). The tert-butyl compounds tested were in the form of solvents. Each reaction was run at room temperature for about 4.5 to 5 hours. At the end of the reaction time, each mixture was analyzed using the UPLC technique, as described in EXAMPLE 1. The results in TABLE II show that the transesterification reactions in the presence of certain tert-butyl compounds, namely, tert-butyl benzoate, tert-butyl methacrylate, tert butyl propionate, and tert-butyl bromoacetate, yielded significant amounts of Z-Asp(OtBu)2. In contrary, methyl-tert butyl ether (MTBE), and tert-butyl formate were not as effective for producing Z-Asp(OtBu)2.
Reference: [1] Patent: US2003/236430, 2003, A1, . Location in patent: Page column 4
  • 16
  • [ 27486-72-2 ]
  • [ 5545-52-8 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1964, vol. 673, p. 208 - 220
  • 17
  • [ 36702-55-3 ]
  • [ 5545-52-8 ]
Reference: [1] Chemische Berichte, 1972, vol. 105, # 11, p. 3650 - 3657
  • 18
  • [ 4668-42-2 ]
  • [ 5545-52-8 ]
Reference: [1] Gazzetta Chimica Italiana, 1964, vol. 94, p. 695 - 709
  • 19
  • [ 88966-25-0 ]
  • [ 5545-52-8 ]
Reference: [1] Gazzetta Chimica Italiana, 1964, vol. 94, p. 695 - 709
  • 20
  • [ 4668-44-4 ]
  • [ 5545-52-8 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1964, vol. 673, p. 208 - 220
  • 21
  • [ 4668-43-3 ]
  • [ 5545-52-8 ]
Reference: [1] Chemische Berichte, 1972, vol. 105, # 11, p. 3650 - 3657
  • 22
  • [ 3057-74-7 ]
  • [ 501-53-1 ]
  • [ 5545-52-8 ]
Reference: [1] Journal of Organic Chemistry, 1963, vol. 28, p. 1251 - 1253
  • 23
  • [ 5545-52-8 ]
  • [ 3057-74-7 ]
Reference: [1] Synthesis, 2011, # 18, p. 2893 - 2896
[2] Tetrahedron, 1972, vol. 28, p. 2649 - 2654
[3] Chemische Berichte, 1972, vol. 105, # 11, p. 3650 - 3657
  • 24
  • [ 5545-52-8 ]
  • [ 4668-42-2 ]
Reference: [1] Synthetic Communications, 1992, vol. 22, # 6, p. 883 - 891
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