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[ CAS No. 77128-73-5 ] {[proInfo.proName]}

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Chemical Structure| 77128-73-5
Chemical Structure| 77128-73-5
Structure of 77128-73-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 77128-73-5 ]

CAS No. :77128-73-5 MDL No. :MFCD00151938
Formula : C25H23NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :GBROUWPNYVBLFO-QHCPKHFHSA-N
M.W :401.45 Pubchem ID :978356
Synonyms :
Fmoc-N-Me-Phe-OH

Calculated chemistry of [ 77128-73-5 ]

Physicochemical Properties

Num. heavy atoms : 30
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.2
Num. rotatable bonds : 8
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 114.56
TPSA : 66.84 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.94
Log Po/w (XLOGP3) : 4.83
Log Po/w (WLOGP) : 4.56
Log Po/w (MLOGP) : 3.63
Log Po/w (SILICOS-IT) : 3.99
Consensus Log Po/w : 3.99

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.29
Solubility : 0.00207 mg/ml ; 0.00000515 mol/l
Class : Moderately soluble
Log S (Ali) : -5.97
Solubility : 0.000433 mg/ml ; 0.00000108 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.04
Solubility : 0.0000368 mg/ml ; 0.0000000916 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 4.06

Safety of [ 77128-73-5 ]

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 [ 77128-73-5 ]

* 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 [ 77128-73-5 ]
  • Downstream synthetic route of [ 77128-73-5 ]

[ 77128-73-5 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 84000-03-3 ]
  • [ 77128-73-5 ]
YieldReaction ConditionsOperation in experiment
80% With triethylsilane; trifluoroacetic acid In chloroform at 20℃; The Fmoc-phenylalaninyloxazolidinone (4.60g, 11.6mmol) was dissolved in chloroform (58mL). Trifluoroacetic acid (2.68mL, 34.8equiv) and triethylsilane (5.56mL, 34.8equiv) were added to the solution. The reaction mixture was stirred at room temperature until the reaction was complete (24–72h). The solution was concentrated and partitioned between ether and saturated sodium bicarbonate solution. The combined aqueous phase was acidified with 5M hydrochloric acid to pH 2 and extracted with ethyl acetate. The desired organic phase was then dried (MgSO4) and concentrated to give the product as a dark yellow oil. The crude product was dissolved in dichloromethane and evaporated repeatedly to give Fmoc-N-methylphenylalanine as a brown solid (3.73g, 80percent): mp 106–107°C; LRMS (ESI) m/z [M+H]+ 402.1 (100percent); 1H NMR (300MHz, CDCl3) δH (ppm) (rotamers) 7.74 (2H, d, J=7.5Hz, ArH), 7.49 (1H, d, J=7.8Hz, ArH), 7.43 (1H, t, J=6.9Hz, ArH), 7.37 (2H, t, J=7.5Hz, ArH), 7.25–7.21 (6H, m, ArH), 6.95 (1H, d, J=6.3Hz, ArH), 4.89 (1H, dd, J=5.1, 11.1Hz, NCHCOOH), 4.59–4.53 (1H, m, (Ar)2CHCH2), 4.38 (2H, d, J=14.4Hz, CHCH2O), 3.41–3.35 (1H, m, CHCHHAr), 3.16–3.08 (1H, m, CHCHHAr), 2.77 (3H, s, NCH3), 2.75 (3H, s, NCH3) (1H NMR data was in agreement with that previously described);33 13C NMR (75MHz, CDCl3) δC (ppm) 175.5, 156.5, 143.4, 140.9, 136.4, 128.4, 128.3, 127.3, 126.7, 126.5, 124.6, 124.3, 119.6, 67.6, 60.7, 46.7, 34.3, 32.3.
826 mg With triethylsilane; trifluoroacetic acid In chloroform at 20℃; for 16 h; To a solution of Fmoc-l-Phe 12 (740 mg, 1.91 mmol) in toluene (40 ml) was added 75percent paraformaldehyde (395 mg) and p-toluenesulfonic acid monohydrate (44 mg, 0.23 mmol) and refluxed for 30 min with azeotropic water removal. After cooling to room temperature, the organic layer was washed with 1 N NaHCO3 aq (2.x.20 ml), dried over Na2SO4, filtered, and concentrated in vacuo to yield oxazolidine 13 as an oil. To a solution of the oxazolidine 13 (970 mg, 2.43 mmol) in CHCl3 (10 ml) was added TFA (10 ml) and Et3SiH (0.55 ml, 3.44 mmol). The reaction mixture was stirred for 16 h at room temperature and concentrated in vacuo. The oil was dissolved in CHCl3 and reconcentrated three times and purified by a silica gel column chromatography (n-hexane/acetone 7:1-->4:1-->2:1-->1:1-->1:2) to yield N-Fmoc-N-methyl-Phe 8 (826 mg, 2.06 mmol, 85percent, 2 steps) as a white powder; Mp 137-138 °C; 1H NMR (400 MHz, CDCl3) (isomer I) δH 7.76-6.95 (13H, m), 4.88 (1H, br q) 4.36 (2H, br m) 4.21 (1H, br s), 3.39 (1H, br d), 3.14 (1H, br t), 2.80 (3H, d, J=3.2 Hz); (isomer II) δH 7.76-6.95 (13H, m), 4.56 (2H, m), 4.36 (2H, br m), 4.16 (1H, br s), 3.14 (1H, br t), 2.78 (3H, s).
2.39 g With triethylsilane; trifluoroacetic acid In chloroform at 20℃; General procedure: Paraformaldehyde (1.92 g, 64.0 mmol) and p-toluenesulfonic acid (0.1920 g, 0.12 mmol) were added to a solution of Fmoc-Ala-OH (3.00 g, 9.6 mmol) in toluene (150 mL). The mixture was refluxed for 3 h with Dean–Stark apparatus. After cooled to room temperature, the resultant mixture was washed with saturated NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. After recrystallization with ethylacetate and petroleum ether, the intermediate was obtained without further purification. Trifluoroacetic acid (48.0 mL) and triethylsilane (4.60 mL,28.8 mmol) were added to a solution of above intermediate in CHCl3 (25 mL). The resultant mixture was stirred at room temperature overnight. After concentration, the residue was dissolved in CH2Cl2 and concentrated again; after repeated for three times, the oil liquid was turned to white solid. Then the white solid was dissolved in diethyl ether, concentrated, washed three times with petroleum ether. The residue was purified by flash-column chromatography on silica gel, to yield the white solid product (2.51 g,80percent yield).
Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 17, p. 6918 - 6920
[2] European Journal of Organic Chemistry, 2013, # 21, p. 4509 - 4513
[3] Tetrahedron, 2014, vol. 70, # 14, p. 2351 - 2358
[4] Tetrahedron Letters, 2006, vol. 47, # 11, p. 1691 - 1694
[5] Angewandte Chemie - International Edition, 2008, vol. 47, # 14, p. 2595 - 2599
[6] Tetrahedron, 2012, vol. 68, # 31, p. 6186 - 6192
[7] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 6, p. 1163 - 1170
  • 2
  • [ 2566-30-5 ]
  • [ 28920-43-6 ]
  • [ 77128-73-5 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 15, p. 4615 - 4625
[2] Biochemistry, 2010, vol. 49, # 10, p. 2177 - 2185
  • 3
  • [ 1208119-54-3 ]
  • [ 28920-43-6 ]
  • [ 77128-73-5 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 5, p. 1386 - 1392
  • 4
  • [ 50-00-0 ]
  • [ 35661-40-6 ]
  • [ 77128-73-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 24, p. 5878 - 5881
  • 5
  • [ 35661-40-6 ]
  • [ 77128-73-5 ]
Reference: [1] Tetrahedron, 2012, vol. 68, # 31, p. 6186 - 6192
[2] European Journal of Organic Chemistry, 2013, # 21, p. 4509 - 4513
[3] Tetrahedron, 2014, vol. 70, # 14, p. 2351 - 2358
[4] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 6, p. 1163 - 1170
  • 6
  • [ 28920-43-6 ]
  • [ 77128-73-5 ]
Reference: [1] Tetrahedron, 2012, vol. 68, # 31, p. 6186 - 6192
  • 7
  • [ 63-91-2 ]
  • [ 28920-43-6 ]
  • [ 74-88-4 ]
  • [ 77128-73-5 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 42, p. 7307 - 7310
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