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[ CAS No. 13574-13-5 ] {[proInfo.proName]}

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Chemical Structure| 13574-13-5
Chemical Structure| 13574-13-5
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Product Details of [ 13574-13-5 ]

CAS No. :13574-13-5 MDL No. :MFCD00065569
Formula : C17H23NO6 Boiling Point : -
Linear Structure Formula :- InChI Key :AJDUMMXHVCMISJ-ZDUSSCGKSA-N
M.W :337.37 Pubchem ID :83589
Synonyms :

Calculated chemistry of [ 13574-13-5 ]

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.47
Num. rotatable bonds : 11
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 87.05
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) : -6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.91
Log Po/w (XLOGP3) : 2.23
Log Po/w (WLOGP) : 2.34
Log Po/w (MLOGP) : 1.83
Log Po/w (SILICOS-IT) : 1.99
Consensus Log Po/w : 2.06

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 1.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.8
Solubility : 0.54 mg/ml ; 0.0016 mol/l
Class : Soluble
Log S (Ali) : -4.01
Solubility : 0.0333 mg/ml ; 0.0000987 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.64
Solubility : 0.0768 mg/ml ; 0.000228 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.3

Safety of [ 13574-13-5 ]

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 [ 13574-13-5 ]

* 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 [ 13574-13-5 ]
  • Downstream synthetic route of [ 13574-13-5 ]

[ 13574-13-5 ] Synthesis Path-Upstream   1~22

  • 1
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  • [ 3190-71-4 ]
Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 9, p. 2755 - 2756
  • 2
  • [ 1676-73-9 ]
  • [ 24424-99-5 ]
  • [ 13574-13-5 ]
YieldReaction ConditionsOperation in experiment
100% at 0℃; Example 28 - Formula 125 - Compound 28aIntermediate B: (S)-5-(Benzyloxy)-2-(tert-butoxycarbonyl)-5-oxopentanoic acid To a solution of compound A (5.0 g, 21 .1 mmol) in dixoane and water (1 :1 , 40 mL) at 0 °C was added Boc20 (5.06 g, 23.1 mmol) and the mixture was stirred overnight. The solvent was removed under reduced pressure and the residue was diluted with water (30 mL), basified with Na2C03 (0.7 g) and washed with EtOAc (3 x 20 mL). The aqueous layer was adjusted to pH 2-3 with a 5 M aqueous HCI solution and extracted with EtOAc (4 x 50 mL). The combined organic extracts were washed with brine, dried over Na2S04 and the solvent was removed under reduced pressure to afford (S)-5-(benzyloxy)-2-(tert-butoxycarbonyl)-5-oxopentanoic acid (7.1 g, 100percent) as a viscous colourless oil.LC-MS (Agilent): Rt 3.40 min; m/z calculated for C17H23NO6 [M+Na]+ 360.15, found 360.1 .
100% at 0℃; To a solution of compound A (5.0 g, 21.1 mmol) in dixoane and water (1:1, 40 mL) at 0° C. was added Boc2O (5.06 g, 23.1 mmol) and the mixture was stirred overnight.
The solvent was removed under reduced pressure and the residue was diluted with water (30 mL), basified with Na2CO3 (0.7 g) and washed with EtOAc (3*20 mL).
The aqueous layer was adjusted to pH 2-3 with a 5 M aqueous HCl solution and extracted with EtOAc (4*50 mL).
The combined organic extracts were washed with brine, dried over Na2SO4 and the solvent was removed under reduced pressure to afford (S)-5-(benzyloxy)-2-(tert-butoxycarbonyl)-5-oxopentanoic acid (7.1 g, 100percent) as a viscous colourless oil.
LC-MS (Agilent): Rt 3.40 min; m/z calculated for C17H23NO6 [M+Na]+ 360.15. found 360.1.
Reference: [1] Patent: WO2012/63085, 2012, A2, . Location in patent: Page/Page column 115
[2] Patent: US2013/225594, 2013, A1, . Location in patent: Paragraph 0425; 0426
[3] Synthetic Communications, 1990, vol. 20, # 15, p. 2235 - 2249
[4] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 2, p. 501 - 517
[5] Organic Syntheses, 1985, vol. 63, p. 160 - 160
[6] Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 4, p. 242 - 249
[7] Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 4, p. 250 - 256
[8] Molecular Crystals and Liquid Crystals (1969-1991), 1989, vol. 170, p. 195 - 214
[9] Doklady Chemistry, 2006, vol. 408, # 1, p. 57 - 60
[10] Organic and Biomolecular Chemistry, 2007, vol. 5, # 12, p. 1915 - 1923
[11] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 12, p. 3220 - 3224
[12] Journal of Organic Chemistry, 2016, vol. 81, # 20, p. 9903 - 9911
[13] Chemical Communications, 2017, vol. 53, # 37, p. 5155 - 5158
  • 3
  • [ 132090-12-1 ]
  • [ 13574-13-5 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 3, p. 782 - 786
  • 4
  • [ 13574-84-0 ]
  • [ 13574-13-5 ]
Reference: [1] Russian Journal of Bioorganic Chemistry, 2000, vol. 26, # 6, p. 361 - 368
[2] Helvetica Chimica Acta, 1990, vol. 73, # 1, p. 13 - 24
[3] Pharmaceutical Chemistry Journal, 1981, vol. 15, # 10, p. 720 - 725[4] Khimiko-Farmatsevticheskii Zhurnal, 1981, vol. 15, # 10, p. 37 - 42
  • 5
  • [ 51814-47-2 ]
  • [ 13574-13-5 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 8, p. 2433 - 2438
[2] Organic Letters, 2005, vol. 7, # 9, p. 1723 - 1724
  • 6
  • [ 617-65-2 ]
  • [ 24424-99-5 ]
  • [ 104-15-4 ]
  • [ 100-51-6 ]
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Reference: [1] Chemical communications (Cambridge, England), 2001, # 19, p. 1908 - 1909
  • 7
  • [ 132090-12-1 ]
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Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 3, p. 782 - 786
  • 8
  • [ 56-86-0 ]
  • [ 13574-13-5 ]
Reference: [1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 12, p. 1915 - 1923
[2] Doklady Chemistry, 2006, vol. 408, # 1, p. 57 - 60
[3] Synthetic Communications, 1990, vol. 20, # 15, p. 2235 - 2249
  • 9
  • [ 100-51-6 ]
  • [ 13574-13-5 ]
Reference: [1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 12, p. 1915 - 1923
  • 10
  • [ 100-39-0 ]
  • [ 13574-13-5 ]
Reference: [1] Synthetic Communications, 1990, vol. 20, # 15, p. 2235 - 2249
  • 11
  • [ 18595-34-1 ]
  • [ 1676-73-9 ]
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Reference: [1] Justus Liebigs Annalen der Chemie, 1968, vol. 716, p. 175 - 185
  • 12
  • [ 1070-19-5 ]
  • [ 1676-73-9 ]
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Reference: [1] Justus Liebigs Annalen der Chemie, 1964, vol. 673, p. 196 - 207
  • 13
  • [ 1676-73-9 ]
  • [ 16965-08-5 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1972, p. 1523 - 1526
  • 14
  • [ 13574-13-5 ]
  • [ 72086-72-7 ]
Reference: [1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 12, p. 1915 - 1923
[2] Organic and Biomolecular Chemistry, 2007, vol. 5, # 9, p. 1459 - 1465
[3] Chemical Communications, 2005, # 37, p. 4652 - 4654
[4] Tetrahedron Letters, 1998, vol. 39, # 15, p. 2099 - 2102
[5] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 3, p. 331 - 336
[6] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 8, p. 1498 - 1509
[7] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 11, p. 4836 - 4846
[8] Journal of Organic Chemistry, 1987, vol. 52, # 24, p. 5331 - 5341
[9] Patent: WO2012/109164, 2012, A1,
[10] Tetrahedron Letters, 2014, vol. 55, # 14, p. 2274 - 2276
[11] Heterocycles, 2015, vol. 90, # 2, p. 1309 - 1316
  • 15
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  • [ 24277-39-2 ]
Reference: [1] Chemistry - An Asian Journal, 2012, vol. 7, # 9, p. 2052 - 2060
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1531 - 1544
  • 16
  • [ 13574-13-5 ]
  • [ 74-88-4 ]
  • [ 59279-58-2 ]
YieldReaction ConditionsOperation in experiment
82% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3 h; Step 1
Methyl iodide (1.01 mL, 16.3 mmol) was added dropwise to a solution of (2S)-5-(benzyloxy)-2-[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acid XII (5.00 g, 14.82 mmol) and K2CO3 (2.25 g, 16.3 mmol) in DMF (25 mL) at r.t.
The reaction mixture was stirred about 3 h at r.t. before adding additional methyl iodide (1.01 mL, 16.3 mmol).
EtOAc was then added to the reaction and washed 3*10percent Na2S2O3 and dried over MgSO4.
The solvent was removed under reduced pressure and the crude product was purified on a silica gel column (100:1 and then 50:1 CHCl3/MeOH) to give 5-benzyl 1-methyl (2S)-2-[(tert-butoxy)carbonyl]amino}pentanedioate XIII (4.20 g, 12.23 mmol, 82percent yield). ESIMS found for C18H25NO6 m/z 352 (M+H).
82% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3 h; Step 1[00181] Methyl iodide (1.01 mL, 16.3 mmol) was added dropwise to a solution of (2S)-5-(benzyloxy)-2-[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acid XII (5.00 g, 14.82 mmol) and K2CO3 (2.25 g, 16.3 mmol) in DMF (25 mL) at room temperature The reaction mixture was stirred about 3 h at room temperature before adding additional methyl iodide (1.01 mL, 16.3 mmol). EtOAc was then added to the reaction and washed 3x 10percent Na2S203 and dried over MgSC^. The solvent was removed under reduced pressure and the crude product was purified on a silica gel column (100: 1 and then 50: 1 CHCl3/MeOH) to give 5-benzyl 1-methyl (2S)-2-[(tert-butoxy)carbonyl]amino} pentanedioate XIII (4.20 g, 12.23 mmol, 82percent yield). ESIMS found for Ci8H25N06 mlz 352 (M+H).
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 5, p. 1899 - 1913
[2] Patent: US2008/318957, 2008, A1, . Location in patent: Page/Page column 41-42
[3] Patent: WO2012/109164, 2012, A1, . Location in patent: Page/Page column 39
[4] Organic and Biomolecular Chemistry, 2007, vol. 5, # 12, p. 1915 - 1923
[5] Organic Letters, 2016, vol. 18, # 9, p. 1968 - 1971
  • 17
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  • [ 77-78-1 ]
  • [ 59279-58-2 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With potassium carbonate In acetone for 0.166667 h; Inert atmosphere
Stage #2: at 20℃; for 1 h; Inert atmosphere
Boc-L-Glu(OBn)OH 3 (5 g,14.82 mmol) was added to a 50 mL round bottom flask containing acetone (25 mL).Potassium carbonate (4097 mg, 29.64 mmol) was then added. The reaction mixture wasstirred for 10 minutes and dimethylsulphate (1.55 mL, 16.3 mmol) was addedand stirred for 1 hour at rt. Thereaction was monitored by TLC and showed complete disappearance of startingmaterial. After removal of acetone, water was added and extracted with ethylacetate. The resultant organic layer was dried over sodium sulphate andconcentrated to obtain compound 4 asa colorless liquid.(4.95 g , 95percent). [α]21D = 23 (c 0.1, CHCl3). 1HNMR: (CDCl3, 400 MHz) 1.39(s, 9H), 1.88-2.03 (m, 1H), 2.13-2.20 (m, 1H), 2.35-2.49 (m, 2H), 3.66 (s, 3H),4.30-4.31 (m, 1H), 5.07 (s, 2H), 5.25-5.27 (d, 1H, J = 7.6 Hz), 7.24-7.33 (m, 5H). 13C NMR: (CDCl3,100 MHz) 27.6, 28.2, 30.2, 52.3, 52.8, 66.4, 79.9, 128.2, 128.5, 135.8, 155.4,172.4, 172.7. IR (KBr) 3372, 2978, 1716, 1513, 1455, 1392,1367, 1252, 1214, 1165, 1051, 1028, 873, 781, 751, 699, 579 cm-1.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 14, p. 2274 - 2276
  • 18
  • [ 67-56-1 ]
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  • [ 59279-58-2 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 15, p. 2099 - 2102
[2] Heterocycles, 2015, vol. 90, # 2, p. 1309 - 1316
[3] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 3, p. 331 - 336
[4] Angewandte Chemie - International Edition, 2000, vol. 39, # 19, p. 3447 - 3450
[5] Patent: US2010/105737, 2010, A1, . Location in patent: Page/Page column 32
  • 19
  • [ 186581-53-3 ]
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Reference: [1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 9, p. 1459 - 1465
[2] Journal of Organic Chemistry, 1987, vol. 52, # 24, p. 5331 - 5341
[3] Carbohydrate Research, 1976, vol. 47, p. 49 - 61
[4] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 8, p. 1498 - 1509
[5] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 11, p. 4836 - 4846
[6] Journal of Organic Chemistry, 1986, vol. 51, # 8, p. 1282 - 1286
[7] Organic Letters, 2003, vol. 5, # 16, p. 2963 - 2965
  • 20
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  • [ 59279-58-2 ]
Reference: [1] Chemical Communications, 2005, # 37, p. 4652 - 4654
  • 21
  • [ 13574-13-5 ]
  • [ 18107-18-1 ]
  • [ 59279-58-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 5, p. 1921 - 1924
  • 22
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  • [ 218943-30-7 ]
Reference: [1] Organic Letters, 2000, vol. 2, # 13, p. 1943 - 1946
[2] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 20, p. 3331 - 3340
[3] RSC Advances, 2014, vol. 4, # 70, p. 37419 - 37422
[4] Patent: WO2017/37142, 2017, A1,
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