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[ CAS No. 98541-64-1 ] {[proInfo.proName]}

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Chemical Structure| 98541-64-1
Chemical Structure| 98541-64-1
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Product Details of [ 98541-64-1 ]

CAS No. :98541-64-1 MDL No. :MFCD01318414
Formula : C8H13NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :HRJDEHQWXAPGBG-YFKPBYRVSA-N
M.W :187.19 Pubchem ID :2763194
Synonyms :

Calculated chemistry of [ 98541-64-1 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.75
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.25
TPSA : 64.63 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) : -6.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.64
Log Po/w (XLOGP3) : 0.66
Log Po/w (WLOGP) : 0.44
Log Po/w (MLOGP) : 0.12
Log Po/w (SILICOS-IT) : 0.32
Consensus Log Po/w : 0.63

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.15
Solubility : 13.2 mg/ml ; 0.0704 mol/l
Class : Very soluble
Log S (Ali) : -1.59
Solubility : 4.78 mg/ml ; 0.0255 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.06
Solubility : 16.2 mg/ml ; 0.0867 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.69

Safety of [ 98541-64-1 ]

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 [ 98541-64-1 ]

* 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 [ 98541-64-1 ]
  • Downstream synthetic route of [ 98541-64-1 ]

[ 98541-64-1 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 3262-72-4 ]
  • [ 98541-64-1 ]
YieldReaction ConditionsOperation in experiment
72% With dimethyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; acetonitrile at -55℃; for 2 h; Inert atmosphere Example 2; Standard Procedure for the Synthesis of Boc-Imidazol-1-yl-Ala (AA2); Step 2-1. Boc-Serine-β-lactone (AA2-1).; This procedure is based on that found in the literature (Vederas, J. C.; et al. J. Am. Chem. Soc. 1987, 109, 4649-4659). Into a dry 250 mL 3-neck flask equipped with a mechanical stirrer under a nitrogen atmosphere was added triphenylphosphine (4.5 g, 17.1 mmol, 1.1 eq), followed by 100 mL of an anhydrous THF:CH3CN (1:9) mixture. The mixture was stirred until a solution was obtained, then cooled to -55° C. (bath temperature) and dimethylazodicarboxylate (DMAD, 1.9 mL, 17.1 mmol, 1.1 eq) added dropwise over 10 min. After the addition, the mixture was stirred for 20 min and a solution of Boc-Ser-OH (3.18 g, 15.5 mmol, 1.0 eq.) in 50 mL of anhydrous THF:CH3CN (1:9) was added dropwise over 30 min. The mixture was stirred at -55° C. for 1.5 h, then the bath was removed and the solution allowed to warm slowly to room temperature. Once the mixture reached room temperature, the solvent was evaporated under reduced pressure. The resulting yellow oil was purified by flash chromatography [gradient, hexanes:EtOAc, (80:20) to (60:40)] to give 2.10 g of AA2-1 as a white solid in 72percent yield. Purification of the crude material is best performed on the same day as the reaction to avoid decomposition. DCM can be added to help dissolve the crude residue.TLC (Hex/EtOAc, 60/40): Rf=0.55 (CMA)
53% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at -78 - 20℃; for 2.83333 h; Inert atmosphere Anhydrous tetrahydrofuran (THF) (100 mL) was added dropwise to triphenylphosphine (Ph3P) (6.3 g, 24.00 mmol), stirred at -78 ° C under argon for more than 10 min. A solution of diethyl azodicarboxylate (DEAD) was added dropwise and the resulting solution was stirred for 10 min. The above tetrahydrofuran mixed solution was added dropwise to a solution of N- (tert-butoxycarbonyl 1) -L-serine (5 g, 24.36 mmol) and stirred for more than 20 min. The resulting solution was stirred at -78 ° C for 20 min and then further stirred at room temperature for 2.5 h. The solvent was removed from tetrahydrofuran and the crude product was purified by chromatography on a column (3: 1 by volume ethane / ethyl acetate). And finally purified by recrystallization from ethyl acetate / n-hexane to give white solid compound 2 (2.4 g, yield 53percent).
Reference: [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 3, p. 1330 - 1340
[2] Journal of the American Chemical Society, 1985, vol. 107, # 24, p. 7105 - 7109
[3] Patent: US2010/93720, 2010, A1, . Location in patent: Page/Page column 37
[4] Heterocycles, 2001, vol. 55, # 1, p. 1 - 4
[5] Journal of Medicinal Chemistry, 1996, vol. 39, # 22, p. 4430 - 4438
[6] Canadian Journal of Chemistry, 1994, vol. 72, # 4, p. 1066 - 1075
[7] Journal of the American Chemical Society, 1989, vol. 111, # 11, p. 3973 - 3976
[8] Journal of Organic Chemistry, 2008, vol. 73, # 2, p. 517 - 521
[9] Patent: CN106083856, 2016, A, . Location in patent: Paragraph 0019; 0023; 0026
[10] Organic letters, 2000, vol. 2, # 23, p. 3603 - 3606
[11] Organic and Biomolecular Chemistry, 2008, vol. 6, # 20, p. 3661 - 3663
[12] Tetrahedron Letters, 2006, vol. 47, # 6, p. 1019 - 1021
[13] European Journal of Organic Chemistry, 2014, vol. 2014, # 35, p. 7806 - 7809
[14] Organic Syntheses, 1992, vol. 70, p. 10 - 10
[15] MedChemComm, 2016, vol. 7, # 11, p. 2136 - 2144
[16] Angewandte Chemie, International Edition, 2009, vol. 48, p. 4718 - 4724[17] Angewandte Chemie, 2009, vol. 121, p. 4812 - 4818
[18] Canadian Journal of Chemistry, 1994, vol. 72, # 4, p. 1051 - 1065
[19] Journal of Organic Chemistry, 1996, vol. 61, # 10, p. 3548 - 3550
[20] European Journal of Organic Chemistry, 2002, # 23, p. 3995 - 4004
[21] Organic and Biomolecular Chemistry, 2005, vol. 3, # 6, p. 1058 - 1066
[22] Patent: EP1205471, 2002, A1, . Location in patent: Page 7
[23] Patent: US6953788, 2005, B1, . Location in patent: Page/Page column 50
[24] Journal of Medicinal Chemistry, 2010, vol. 53, # 15, p. 5770 - 5781
[25] Journal of Medicinal Chemistry, 2012, vol. 55, # 10, p. 4824 - 4836
[26] Advanced Synthesis and Catalysis, 2016, vol. 358, # 1, p. 34 - 40
[27] Patent: US9321743, 2016, B2, . Location in patent: Page/Page column 9
[28] Journal of Organometallic Chemistry, 2018, vol. 876, p. 1 - 9
[29] Patent: WO2018/167506, 2018, A1, . Location in patent: Page/Page column 28
  • 2
  • [ 3262-72-4 ]
  • [ 98541-64-1 ]
Reference: [1] Patent: US2003/27800, 2003, A1,
[2] Patent: US2003/130237, 2003, A1,
  • 3
  • [ 24424-99-5 ]
  • [ 98541-64-1 ]
Reference: [1] Heterocycles, 2001, vol. 55, # 1, p. 1 - 4
[2] Advanced Synthesis and Catalysis, 2016, vol. 358, # 1, p. 34 - 40
  • 4
  • [ 2766-43-0 ]
  • [ 98541-64-1 ]
Reference: [1] Journal of Organometallic Chemistry, 2018, vol. 876, p. 1 - 9
  • 5
  • [ 98541-64-1 ]
  • [ 76387-70-7 ]
Reference: [1] Journal of the American Chemical Society, 1985, vol. 107, # 24, p. 7105 - 7109
  • 6
  • [ 4498-99-1 ]
  • [ 98541-64-1 ]
  • [ 61925-78-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 10, p. 2992 - 3004
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