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[ CAS No. 7524-50-7 ] {[proInfo.proName]}

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Chemical Structure| 7524-50-7
Chemical Structure| 7524-50-7
Structure of 7524-50-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 7524-50-7 ]

CAS No. :7524-50-7 MDL No. :MFCD00012489
Formula : C10H14ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :SWVMLNPDTIFDDY-FVGYRXGTSA-N
M.W :215.68 Pubchem ID :75736
Synonyms :
H-Phe-OMe.hydrochloride

Calculated chemistry of [ 7524-50-7 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 56.79
TPSA : 52.32 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) : -6.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.45
Log Po/w (WLOGP) : 1.53
Log Po/w (MLOGP) : 1.7
Log Po/w (SILICOS-IT) : 1.37
Consensus Log Po/w : 1.21

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.14
Solubility : 1.55 mg/ml ; 0.00718 mol/l
Class : Soluble
Log S (Ali) : -2.15
Solubility : 1.51 mg/ml ; 0.00701 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.57
Solubility : 0.586 mg/ml ; 0.00272 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.75

Safety of [ 7524-50-7 ]

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 [ 7524-50-7 ]

* 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 [ 7524-50-7 ]
  • Downstream synthetic route of [ 7524-50-7 ]

[ 7524-50-7 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 7524-50-7 ]
  • [ 5241-58-7 ]
YieldReaction ConditionsOperation in experiment
76% at 20℃; The intermediate 1 was dissolved in 20percent aqueous ammonia, and the reaction was stirred at room temperature for 20 hours. After the reaction was completed, 50 mL of ethyl acetate was added and extracted three times.The organic layer was combined, and the solvent was evaporated to dryness to give Intermediate 2,White solid, 2.5 g, yield 76percent.
59% With ammonia In water at 20℃; for 64 h; PREPARATION 17; Preparation of (S)-3-phenylpropane-l,2-diamine; A. A mixture of L-phenylalanine methyl ester hydrochloride (6.50 g, 30.1 mmol) and ammonium hydroxide solution (28percent in water, 15 mL) in water (60 mL) was stirred at ambient temperature for 64 h. The aqueous layer was extracted with dichloromethane (6 x 100 mL), and the combined organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford (5)-2-amino-3-phenylpropanamide as a colorless solid in 59percent yield (2.92 g): 1H NMR (300 MHz, DMSO-4) δ 7.38-7.21
19.5 g
Stage #1: With sodium hydrogencarbonate In chloroform
Stage #2: With ammonium hydroxide In toluene at 20℃; for 24 h;
To a solution of L-Phenylalanine methyl ester hydrochloride (26.1 g, 121 mmol, 1 eq) in chloroform (200 ml) was added saturated NaHC03 solution until pH paper indicated the solution to be basic. The free amine was extracted with chloroform (2 x 200 ml), dried over MgS04 and evaporated under reduced pressure. The resulting L-Phenylalanine methyl ester was dissolved in toluene (300 ml) and to this solution was added saturated ammonium hydroxide solution (150 ml). The reaction was stirred at room temperature for 24 hours before being evaporated to dryness under reduced pressure. The crude product did not require further purification (19.5 g, 1 19 mmol, 98 percent). 1H NMR (400 MHz, DMSO): δ = 1 .90 (brs, 2H, NH2), 2.59 (dd, J = 13.4 Hz, 8.3 Hz, 1 H), 2.92 (dd, J = 13.4 Hz, J = 5.1 Hz, 1 H), 3.34 (dd, J = 8.3 Hz, 5.1 Hz, 1 H), 6.96 (brs, 1 H), 7.16-7.30 (m, 5H), 7.32 (brs, 1 H); 13C NMR (100.6 MHz, CDCI3): δ = 42.0, 57.1 , 126.9, 128.9, 130.2, 139.8, 177.6.
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[2] Organic and Biomolecular Chemistry, 2012, vol. 10, # 30, p. 6074 - 6086
[3] Chemistry - An Asian Journal, 2011, vol. 6, # 6, p. 1321 - 1324
[4] Bulletin de la Societe Chimique de France, 1989, # 5, p. 673 - 676
[5] Patent: CN108610292, 2018, A, . Location in patent: Paragraph 0041; 0051; 0052
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[7] Patent: WO2008/127349, 2008, A2, . Location in patent: Page/Page column 104
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[9] European Journal of Medicinal Chemistry, 1985, vol. 20, # 6, p. 509 - 512
[10] European Journal of Medicinal Chemistry, 1986, vol. 21, # 4, p. 333 - 338
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[13] Chemistry - A European Journal, 2008, vol. 14, # 35, p. 10888 - 10891
[14] Patent: WO2014/68341, 2014, A2, . Location in patent: Page/Page column 41
  • 2
  • [ 7524-50-7 ]
  • [ 13122-90-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 1992, vol. 27, # 3, p. 179 - 186
[2] Chemical Communications, 2014, vol. 50, # 42, p. 5551 - 5553
[3] Journal of the American Chemical Society, 2016, vol. 138, # 38, p. 12387 - 12394
  • 3
  • [ 7524-50-7 ]
  • [ 17193-39-4 ]
Reference: [1] Synthesis, 2009, # 14, p. 2440 - 2446
[2] Journal of Medicinal Chemistry, 1994, vol. 37, # 7, p. 913 - 923
  • 4
  • [ 7524-50-7 ]
  • [ 17193-39-4 ]
  • [ 117160-99-3 ]
Reference: [1] Advanced Synthesis and Catalysis, 2001, vol. 343, # 8, p. 802 - 808
  • 5
  • [ 5619-07-8 ]
  • [ 7524-50-7 ]
  • [ 13033-84-6 ]
Reference: [1] Patent: WO2010/148191, 2010, A2, . Location in patent: Page/Page column 45-49; 59
  • 6
  • [ 7524-50-7 ]
  • [ 65864-22-4 ]
Reference: [1] Liebigs Annalen der Chemie, 1992, # 9, p. 921 - 926
[2] Journal fur Praktische Chemie - Chemiker - Zeitung, 1996, vol. 338, # 3, p. 251 - 256
[3] Advanced Synthesis and Catalysis, 2012, vol. 354, # 17, p. 3327 - 3332
  • 7
  • [ 7524-50-7 ]
  • [ 132278-63-8 ]
Reference: [1] Beilstein Journal of Organic Chemistry, 2012, vol. 8, p. 1385 - 1392
[2] Chemistry - A European Journal, 2015, vol. 21, # 28, p. 10031 - 10038
  • 8
  • [ 24424-99-5 ]
  • [ 7524-50-7 ]
  • [ 87694-53-9 ]
Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 135, p. 142 - 158
  • 9
  • [ 7524-50-7 ]
  • [ 52071-65-5 ]
Reference: [1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2004, vol. 59, # 7, p. 817 - 820
  • 10
  • [ 7524-50-7 ]
  • [ 30189-48-1 ]
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[4] New Journal of Chemistry, 2018, vol. 42, # 6, p. 4344 - 4351
  • 11
  • [ 7524-50-7 ]
  • [ 84773-29-5 ]
Reference: [1] Journal of Organometallic Chemistry, 1986, vol. 317, p. 93 - 104
  • 12
  • [ 7524-50-7 ]
  • [ 141403-49-8 ]
Reference: [1] European Journal of Medicinal Chemistry, 1989, vol. 24, # 5, p. 503 - 510
  • 13
  • [ 7524-50-7 ]
  • [ 52485-51-5 ]
Reference: [1] Tetrahedron, 2014, vol. 70, # 31, p. 4602 - 4610
[2] Chemical Communications, 2015, vol. 51, # 49, p. 9991 - 9994
  • 14
  • [ 7524-50-7 ]
  • [ 114457-94-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 9, p. 1416 - 1426
[2] Patent: WO2012/48745, 2012, A1,
[3] Synthesis (Germany), 2013, vol. 45, # 20, p. 2843 - 2852
[4] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 8, p. 1958 - 1962
[5] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 15, p. 4031 - 4044
  • 15
  • [ 7524-50-7 ]
  • [ 205393-22-2 ]
Reference: [1] Patent: WO2012/48745, 2012, A1,
  • 16
  • [ 7524-50-7 ]
  • [ 868539-96-2 ]
Reference: [1] Patent: WO2014/18807, 2014, A1,
[2] Patent: WO2016/170544, 2016, A1,
  • 17
  • [ 7524-50-7 ]
  • [ 745017-94-1 ]
Reference: [1] Patent: WO2012/166560, 2012, A1,
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