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[ CAS No. 85909-04-2 ] {[proInfo.proName]}

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Chemical Structure| 85909-04-2
Chemical Structure| 85909-04-2
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Product Details of [ 85909-04-2 ]

CAS No. :85909-04-2 MDL No. :MFCD18206247
Formula : C10H19NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :WOSTYWSKGONZPI-UHFFFAOYSA-N
M.W : 217.26 Pubchem ID :13112352
Synonyms :

Calculated chemistry of [ 85909-04-2 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 8
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 55.98
TPSA : 64.63 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) : -6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.77
Log Po/w (XLOGP3) : 1.11
Log Po/w (WLOGP) : 1.46
Log Po/w (MLOGP) : 1.13
Log Po/w (SILICOS-IT) : 0.97
Consensus Log Po/w : 1.49

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.36
Solubility : 9.52 mg/ml ; 0.0438 mol/l
Class : Very soluble
Log S (Ali) : -2.06
Solubility : 1.89 mg/ml ; 0.0087 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.13
Solubility : 1.61 mg/ml ; 0.00741 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.17

Safety of [ 85909-04-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 85909-04-2 ]

* 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 [ 85909-04-2 ]
  • Downstream synthetic route of [ 85909-04-2 ]

[ 85909-04-2 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 85909-04-2 ]
  • [ 13031-60-2 ]
YieldReaction ConditionsOperation in experiment
90% With hydrogenchloride In ethyl acetate for 3.5 h; Compound 44a was obtained as a white solid in 90percent yield from 43a upon treatment with HCl/EtOAc [29]. No starting material was detected by TLC (1:3 hexane:EtOAc) after 3.5 h of stirring, mp 103 °C 1H NMR (300 MHz, MeOD) ppm δ 3.71 (s, 2H), 3.06 (t, 2H, J = 7.5 Hz), 2.54 (t, 2H, J = 7.2 Hz), 2.03 (quint, 2H, J = 7.5 Hz). 13C NMR (75 MHz, MeOD) ppm δ 174.5, 52.4, 40.1, 31.5, 23.67. MS (CI+): m/z 118.09 (MH+, 85.36), 102.07 ([MH+-CH4], 39.19), 101.06 ([M+ - CH4], 82.96), 87.06 ([MH+ - OMe], 100), 86.06 ([MH+ - HOMe], 76.79). HRMS: calcd. for C5H12NO2 (MH+, CI+) 118.0868 found 118.0883.
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 2, p. 447 - 467
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  • [ 67-56-1 ]
  • [ 85909-08-6 ]
  • [ 75178-87-9 ]
  • [ 85909-04-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2009, vol. 48, # 7, p. 1324 - 1327
  • 3
  • [ 57294-38-9 ]
  • [ 74-88-4 ]
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YieldReaction ConditionsOperation in experiment
83% With potassium carbonate In acetone at 20 - 45℃; for 12 h; Example 12: Synthesis of (2S,5R)-2-(5-(3-aminopropyl)-l ,3,4-oxadiazol-2-yl)-7-oxo-l ,6- diazabicyclo[3.2.1 loctan-6-yl hydrogen sulfate (Compound 720) Step 1: Synthesis of 4-(tert-butoxycarbonylamino)butanoic acid: To an aqueous solution of 4-aminobutanoic acid (25 g, 242 mmol) in H20 (500 mL) at rt was added Na2C03 (75 g, 726 mmol), followed by Boc20 (95 g, 435 mmol) in THF (200 mL). The reaction mixture was stirred at rt for 12 hrs then concentrated under reduced pressure. The aqueous residue was extracted with Et20, then the aqueous layer was acidified to pH 4-5 with citric acid and extracted with EtOAc. The combined organic layer was dried over Na2S04, and concentrated to afford 4-(ieri-butoxycarbonylamino)butanoic acid (45 g, 90percent) as a colorless oil. ESI-MS (EI+, m/z): 226 [M+Na]+. Step 2: Synthesis of methyl 4-(tert-butoxycarbonylamino)butanoate: To a solution of 4-(ieri-butoxycarbonylamino)butanoic acid (7.0 g, 34.5 mmol) and K2CO3 (9.5 g, 68.9 mmol) in acetone (70 mL) was added Mel (7.5 g, 51.8 mmol) at rt. The reaction solution was stirred at 45 °C for 12 hrs. The mixture was washed with water and saturated sodium chloride, dried over Na2S04, and concentrated to afford methyl 4-(tert- butoxycarbonylamino)butanoate (6.2 g, 83percent) as a yellow oil. ESI-MS (EI+, m/z) 240 [M+Na]+. Step 3: Synthesis of tert-butyl 4-hydrazinyl-4-oxobutylcarbamate: To a solution of methyl 4-(ieri-butoxycarbonylamino)butanoate (21.0 g, 96.8 mmol) in MeOH (180 mL) was added NH2NH2.H20 (28.0 g, 483mmol) at rt. The mixture was stirred at 65 °C for 12 hrs then concentrated under reduced pressure. The crude material was dissolved in DCM (400 mL). The organic layer was washed with water (2x), and saturated sodium chloride (2x), dried over Na2S04, and concentrated to afford ieri-butyl 4-hydrazinyl- 4-oxobutylcarbamate (18.9 g, 90percent) as a white solid. ESI-MS (EI+, m/z): 240 [M+Na]+. Step 4: Synthesis of tert-butyl4-(2-((2S,5R)-6-(benzyloxy)-7-oxo-l ,6-diaza- bicyclo[ 3.2.1 ]octane-2-carbonyl)hydrazinyl)-4-oxobutylcarbamate: To a 0 °C solution of (25,5 ?)-6-(benzyloxy)-7-oxo-l,6-diaza-bicyclo[3.2.1]octane-2- carboxylic acid (12.0 g, 43.5 mmol) and ieri-butyl 4-hydrazinyl-4-oxobutylcarbamate (10.5 g, 47.8 mmol) in CH2C12 (360 mL) was added HATU (19.6 g, 52.2 mmol) and DIPEA (16.6 g, 130.5 mmol). The mixture was allowed to warm to rt, was stirred at rt for 12 hrs then diluted with CH2C12 (300 mL), washed with water (2x) and saturated sodium chloride (2x), dried over Na2S04, and concentrated. The residue was purified by silica gel column chromatography (gradient elution 50-80percent EtO Ac/petroleum ether) to afford ieri-butyl 4-(2- ((25',5 ?)-6-(benzyloxy)-7-oxo-l,6-diaza-bicyclo [3.2.1]octane-2-carbonyl)hydrazinyl)-4- oxobutylcarbamate (19.3 g, 93percent) as a white solid. ESI-MS (EI+, m/z): 476 [M+H]+. Step 5: Synthesis of tert-butyl 3-(5-((2S,5R)-6-(benzyloxy)-7-oxo-l,6-diaza- bicyclo[3.2.1]octan-2-yl)-l,3,4-oxadiazol-2-yl)propylcarbamate: Method A: Tf20 (8.0 mL, 0.0474 mol) was added drop wise to a -78 °C solution of tert-butyl 4-(2- ((25',5 ?)-6-(benzyloxy)-7-oxo-l,6-diaza-bicyclo [3.2.1]octane-2-carbonyl)hydrazinyl)-4- oxobutylcarbamate (7.5 g, 0.0158 mol) and Py (10.2 mL, 0.126 mol) in dry DCM (120 mL). The reaction mixture was allowed to warm to 0 °C then the reaction mixture was stirred at 0 °C for 3 hrs. Sat. NaHCC>3 was added at 0 °C very slowly. The organic layer was separated and the water layer was exacted with DCM (3x). The combined organic layer was washed with water, saturated sodium chloride, dried over Na2S04, and concentrated. The residue was purified by silica gel column (gradient elution 0-25percent EtO Ac/petroleum ether) to afford ieri- butyl 3-(5-((25',5)-6-(benzyloxy)-7-oxo-l,6-diaza-bicyclo[3.2.1]octan-2-yl)-l,3,4- oxadiazol-2-yl)propylcarbamate (3.9 g, 54percent) as a yellow solid. ESI-MS (EI+, m/z): 458 [M+H]+. 1H NMR (500 MHz, CDC13) δ 7.45-7.37 (m, 5H), 5.08 (d, / = 14.5 Hz, 1H), 4.93 (d, / = 14.5 Hz, 1H), 4.70-4.66 (m, 1H), 3.37 (br s, 1H), 3.23-3.21 (m, 2H), 2.94-2.88 (m, 3H), 2.79 (d, / = 14.5 Hz, 1H), 2.30-2.28 (m, 2H), 2.11-1.97 (m, 4H), 1.45 (s, 9H). Method B: To s solution of PPh3 (2.6 g, 10.0 mmol) in dry DCM (60 mL) was added I2 (2.6 g, 10.0 mmol). After I2 was dissolved completely, TEA (3.5 mL, 25.0 mmol) was added quickly at rt. The mixture was stirred for 15 mins. 7ri-butyl 4-(2-((25,,5/?)-6-(benzyloxy)-7-oxo-l ,6-diaza- bicyclo [3.2.1]octane-2-carbonyl)hydrazinyl)-4-oxobutylcarbamate (2.4 g, 5.0 mmol) was added. The mixture was stirred at rt for 1 hr. The solvent was concentrated. EtO Ac (250 mL) was added, and the solution was filtrated to remove POPI13. The filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (gradient elution 0-40percent EtOAc/petroleum ether) to afford ieri-butyl 3-(5-((25',5)-6-(benzyloxy)-7-oxo-l,6- diaza-bicyclo[3.2.1]octan-2-yl)-l,3,4-oxadiazol-2-yl)propylcarbamate (2.0 g, 86percent) as a white solid. ESI-MS (EI+, m/z): 458 [M+H]+. Step 6-8: Following Steps 3-5 in Example 4, replacing ieri-butyl (2-(5-((2S,5R)-6- (benzyloxy)-7-oxo-l,6-diazabicyclo[3.2.1]octan-2-yl)-l ,3,4-oxadiazol-2-yl)ethyl)carbamate in Step 3 with ieri-butyl (3-(5-((2S,5R)-6-(benzyloxy)-7-oxo-l,6-diazabicyclo[3.2.1]octan-2- yl)-l,3,4-oxadiazol-2-yl)propyl)carbamate; (25',5 ?)-2-(5-(3-aminopropyl)-l,3,4-oxadiazol-2- yl)-7-oxo-l,6-diazabicyclo[3.2.1]octan-6-yl hydrogen sulfate (1.48 g) was obtained as a white solid after prep-HPLC purification using ammonium formate buffer. ESI-MS (EI+, m/z): 348.1. 1H NMR (300 MHz, D20) δ 4.74 (d, / = 6.2 Hz, 1H), 4.17 (br s, 1H), 3.17 (br d, / = 12.1 Hz, 1H), 3.05 - 2.95 (m, 4H), 2.89 (d, / = 12.3 Hz, 1H), 2.31 - 2.20 (m, 1H), 2.20 - 2.02 (m, 4H), 2.00 - 1.82 (m, 1H).
83% With potassium carbonate In acetone at 45℃; for 12 h; To a solution of 4-(tert-butoxycarbonylamino)butanoic acid (7.0 g, 34.5 mmol) and K2CO3 (9.5 g, 68.9 mmol) in acetone (70 mL) was added MeI (7.5 g, 51.8 mmol) at rt. The reaction solution was stirred at 45° C. for 12 hrs. The mixture was washed with water and saturated sodium chloride, dried over Na2SO4, and concentrated to afford methyl 4-(tert-butoxycarbonylamino)-butanoate (6.2 g, 83percent) as a yellow oil. ESI-MS (EI+, m/z): 240 [M+Na]+.
Reference: [1] Patent: WO2013/149121, 2013, A1, . Location in patent: Page/Page column 75; 76
[2] Patent: US2015/111864, 2015, A1, . Location in patent: Paragraph 0113; 0115
[3] Farmaco, 2004, vol. 59, # 5, p. 381 - 388
[4] Organic and Biomolecular Chemistry, 2012, vol. 10, # 4, p. 861 - 868
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  • [ 57294-38-9 ]
  • [ 85909-04-2 ]
YieldReaction ConditionsOperation in experiment
90% With dmap; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; Inert atmosphere General procedure: The N-t-Boc protected amino acid/alcohol (5.7 mmol) was dissolved in anhydrous CH2Cl2 (20 mL), under N2, followed by addition of a suitable alcohol/acid (5.7 mmol), DMAP (5.7 mmol), Bop (5.7 mmol) and Et3N (17 mmol). The mixture was stirred at room temperature overnight. The solvent was then evaporated and the residue was dissolved in EtOAc/H2O. The organic phase was washed with concentrated KHSO4 and with saturated NaHCO3 solution. The organic phase was separated, washed with brine, dried over Na2SO4 and evaporated.
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 2, p. 447 - 467
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  • [ 24424-99-5 ]
  • [ 13031-60-2 ]
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Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 22, p. 8730 - 8733
[2] Tetrahedron Letters, 2012, vol. 53, # 45, p. 5996 - 5999,4
[3] Tetrahedron Letters, 2012, vol. 53, # 45, p. 5996 - 5999
  • 6
  • [ 865-33-8 ]
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Reference: [1] Organic Letters, 2013, vol. 15, # 19, p. 5072 - 5075
  • 7
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Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 22, p. 5395 - 5399
[2] Journal of Organic Chemistry, 1983, vol. 48, # 14, p. 2424 - 2426
  • 8
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Reference: [1] ACS Catalysis, 2017, vol. 7, # 5, p. 3157 - 3161
  • 9
  • [ 1314538-55-0 ]
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Reference: [1] Advanced Synthesis and Catalysis, 2014, vol. 356, # 13, p. 2749 - 2755
  • 10
  • [ 67-56-1 ]
  • [ 85909-08-6 ]
  • [ 75178-87-9 ]
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Reference: [1] Angewandte Chemie - International Edition, 2009, vol. 48, # 7, p. 1324 - 1327
  • 11
  • [ 292638-85-8 ]
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Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 5, p. 1537 - 1541[2] Angew. Chem., 2015, vol. 127, # 5, p. 1557 - 1561,5
  • 12
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Reference: [1] ACS Catalysis, 2017, vol. 7, # 5, p. 3157 - 3161
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  • [ 228110-66-5 ]
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Reference: [1] Synlett, 2007, # 3, p. 491 - 493
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Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 14, p. 2424 - 2426
[2] Angewandte Chemie - International Edition, 2012, vol. 51, # 22, p. 5395 - 5399
[3] Patent: WO2013/149121, 2013, A1,
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Reference: [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 4, p. 861 - 868
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  • [ 64-17-5 ]
  • [ 85909-08-6 ]
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  • [ 228110-66-5 ]
Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 22, p. 5395 - 5399
  • 17
  • [ 186581-53-3 ]
  • [ 57294-38-9 ]
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Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 17, p. 2786 - 2788
  • 18
  • [ 58632-95-4 ]
  • [ 85909-04-2 ]
Reference: [1] Farmaco, 2004, vol. 59, # 5, p. 381 - 388
  • 19
  • [ 66866-43-1 ]
  • [ 85909-04-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 5, p. 1537 - 1541[2] Angew. Chem., 2015, vol. 127, # 5, p. 1557 - 1561,5
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Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 5, p. 1537 - 1541[2] Angew. Chem., 2015, vol. 127, # 5, p. 1557 - 1561,5
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