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[ CAS No. 82311-69-1 ] {[proInfo.proName]}

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Chemical Structure| 82311-69-1
Chemical Structure| 82311-69-1
Structure of 82311-69-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 82311-69-1 ]

CAS No. :82311-69-1 MDL No. :MFCD06659110
Formula : C9H10BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :GDMOHOYNMWWBAU-QMMMGPOBSA-N
M.W : 244.09 Pubchem ID :2762259
Synonyms :
H-Phe(3-Br)-OH
Chemical Name :(S)-2-Amino-3-(3-bromophenyl)propanoic acid

Calculated chemistry of [ 82311-69-1 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 53.2
TPSA : 63.32 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.38 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.77
Log Po/w (XLOGP3) : -0.83
Log Po/w (WLOGP) : 1.4
Log Po/w (MLOGP) : -0.39
Log Po/w (SILICOS-IT) : 1.55
Consensus Log Po/w : 0.7

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.97
Solubility : 25.9 mg/ml ; 0.106 mol/l
Class : Very soluble
Log S (Ali) : -0.02
Solubility : 233.0 mg/ml ; 0.956 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.72
Solubility : 0.461 mg/ml ; 0.00189 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 82311-69-1 ]

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 [ 82311-69-1 ]

* 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 [ 82311-69-1 ]
  • Downstream synthetic route of [ 82311-69-1 ]

[ 82311-69-1 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 82278-73-7 ]
  • [ 82311-69-1 ]
YieldReaction ConditionsOperation in experiment
89% With hydrogenchloride In 1,4-dioxane at 20℃; for 16 h; (2S)-3-(3-Bromophenyl)-2-(ter^butoxycarbonylamino)propionic acid (5.0 g, 14.5 mmol) was suspended in 4M HCl in 1 ,4-dioxane (75 mL) and stirred for 16 h at r.t. The white precipitate was filtered and washed with Et2O to give the title compound (3.2 g, 89percent) as a white solid that required no further purification. δH (CDCl3) 8.32 (2H, s), 7.50- 7.48 (2H, m), 7.34-7.29 (2H, m), 4.22 (IH, t, J6.2 Hz), 3.13-3.11 (2H, m).
89% With hydrogenchloride In 1,4-dioxane at 20℃; for 16 h; INTERMEDIATE 65 3 -Bromo-L-phenylalanine(2jS)-3-(3-Bromophenyl)-2-(tert-butoxycarbonylamino)propiomc acid (5.0 g, 14.5 mmol) was suspended in 4M HCl in 1,4-dioxane (75 mL) and stirred for 16 h at r.t.. The white precipitate was filtered and washed with Et2O to give the title compound as a white solid (3.2 g, 89percent) that required no further purification. δH (CDCl3) 8.32 (2H, s), 7.50- 7.48 (2H, m), 7.34-7.29 (2H, m), 4.22 (IH, t, J 6.2 Hz), 3.13-3.11 (2H, m). An exchangeable proton was not observed.
Reference: [1] Patent: WO2008/47109, 2008, A1, . Location in patent: Page/Page column 42
[2] Patent: WO2006/114606, 2006, A1, . Location in patent: Page/Page column 61
  • 2
  • [ 14473-91-7 ]
  • [ 82311-69-1 ]
Reference: [1] Journal of Organic Chemistry, 2009, vol. 74, # 23, p. 9152 - 9157
[2] Tetrahedron, 2016, vol. 72, # 46, p. 7343 - 7347
  • 3
  • [ 14473-91-7 ]
  • [ 82311-69-1 ]
Reference: [1] Catalysis Science and Technology, 2016, vol. 6, # 12, p. 4086 - 4089
  • 4
  • [ 117391-50-1 ]
  • [ 14473-91-7 ]
  • [ 82311-69-1 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 9, p. 1570 - 1576
  • 5
  • [ 14473-91-7 ]
  • [ 82311-69-1 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 40, p. 12977 - 12983
  • 6
  • [ 14473-91-7 ]
  • [ 82311-69-1 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 40, p. 12977 - 12983
  • 7
  • [ 3132-99-8 ]
  • [ 82311-69-1 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 9, p. 1570 - 1576
  • 8
  • [ 14473-91-7 ]
  • [ 82311-69-1 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 40, p. 12977 - 12983
  • 9
  • [ 24424-99-5 ]
  • [ 82311-69-1 ]
  • [ 82278-73-7 ]
YieldReaction ConditionsOperation in experiment
98% With sodium hydrogencarbonate In 1,4-dioxane; water [00121] t-Butylcarbamate (Boc) protection of the amino group of bromophenylalaninewas accomplished, using sodium bicarbonate (3 equivalents), t-butyl dicarbonate (Boc2O, 1.1equivalent) in dioxane and water, to obtain compound 7 in 98percent yield. A methyl sulfone functionality was introduced by treating the bromo compound 7 with copper iodide (0.4 equivalents), cesium carbonate (0.5 equivalents), L-proline (0.8 equivalents), and the sodium salt of methanesulfinic acid (3.9 equivalents) in dimethylsulfoxide (DMSO) at 95-100°C for a totalof 9 hours, with two further additions of copper iodide (0.2 equivalents) and L-proline (0.4 equivalents) during that period. Compound 8 was isolated in 96percent yield. The carboxylic acid of compound 8 was converted to the benzyl ester, compound 9, in 99percent yield, using benzyl alcohol (1 .1 equivalent), dimethylaminopyridine (DMAP, 0.1 equivalent) and N-(3 - dimethylaminopropyl)-N-ethylcarbodiimide (EDC, 1.0 equivalent). The amino group ofcompound 9 is deprotected by adding a 4N solution of HC1 in dioxane to compound 9 at 0°C in methylene chloride. The HC1 salt of the free amino species, compound 10 was isolated in 94percent yield.
Reference: [1] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 3, p. 203 - 206
[2] Patent: WO2014/18748, 2014, A1, . Location in patent: Paragraph 00120; 00121; 00122; 00123; 00124; 00125
[3] Catalysis Science and Technology, 2016, vol. 6, # 12, p. 4086 - 4089
[4] Patent: WO2009/102876, 2009, A1, . Location in patent: Page/Page column 56
  • 10
  • [ 82311-69-1 ]
  • [ 1194550-59-8 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 3, p. 203 - 206
[2] Patent: WO2014/18748, 2014, A1,
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