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[ CAS No. 120728-10-1 ] {[proInfo.proName]}

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Chemical Structure| 120728-10-1
Chemical Structure| 120728-10-1
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Product Details of [ 120728-10-1 ]

CAS No. :120728-10-1 MDL No. :MFCD02682623
Formula : C10H17NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :ROVVUKFHORPDSM-UHFFFAOYSA-N
M.W : 215.25 Pubchem ID :1512646
Synonyms :

Calculated chemistry of [ 120728-10-1 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 54.39
TPSA : 75.63 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.89
Log Po/w (XLOGP3) : 1.23
Log Po/w (WLOGP) : 1.52
Log Po/w (MLOGP) : 0.74
Log Po/w (SILICOS-IT) : 0.66
Consensus Log Po/w : 1.21

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.62
Solubility : 5.17 mg/ml ; 0.024 mol/l
Class : Very soluble
Log S (Ali) : -2.42
Solubility : 0.826 mg/ml ; 0.00384 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.31
Solubility : 10.5 mg/ml ; 0.049 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.25

Safety of [ 120728-10-1 ]

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

Application In Synthesis of [ 120728-10-1 ]

* 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 [ 120728-10-1 ]
  • Downstream synthetic route of [ 120728-10-1 ]

[ 120728-10-1 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 67-56-1 ]
  • [ 120728-10-1 ]
  • [ 215597-35-6 ]
YieldReaction ConditionsOperation in experiment
75% at 0℃; Reflux Stage 1: Methyl 1-aminocyclobutanecarboxylate
Concentrated H2SO4 (10 ml) was added at 0° C. to a solution of 1-(tert-butoxy-carbonylamino)-cyclobutane-1-carboxylic acid (9.29 mmol, 1 equiv.) in MeOH (30 ml), and the reaction was refluxed for 2 hours at 0° C.
The solvent was removed under reduced pressure.
The residue was taken up in distilled water, adjusted to pH 8-9 with saturated sodium hydrogen carbonate solution and extracted with ethyl acetate (2*200 ml).
The combined organic phases were washed with distilled water (2*150 ml) and saturated NaCl solution (2*50 ml) and dried over sodium sulfate.
The solvent was concentrated under reduced pressure to yield the desired product in the form of a white solid. Yield: 75percent
Reference: [1] Patent: US2010/173889, 2010, A1, . Location in patent: Page/Page column 34
  • 2
  • [ 24424-99-5 ]
  • [ 22264-50-2 ]
  • [ 120728-10-1 ]
YieldReaction ConditionsOperation in experiment
75% With sodium hydrogencarbonate In 1,4-dioxane; water at 0 - 20℃; for 12 h; To a stirred solution of 1-aminocyclobutane-1-carboxylic acid (2 g, 17 mmol) in 1,4- dioxane: H2O (20: 20 mL), were added NaHCO3 (4.4 g, 57 mmol) and (Boc)2O (4.5 g, 20.4 mmol) at 0°C and stirred the reaction mixture for about 12 hours at room temperature. After complete conversion of starting material, the reaction mixture was washed with EtOAc (30 mL) to remove the impurities, then aqueous layer was acidified with 1N HCl (PH =2-3) and extracted with CH2Cl2 (2x40 mL). The combined organic extracts were washed with water, brine, dried over Na2S04, filtered and evaporated under reduced pressure. The crude residue was purified by silica gel column chromatography by using 35 percent EtOAc: n-Hexane as an eluent to afford the desired product (2.8 g, yield: 75percent) as an off white solid. 1H MR (300 MHz, CD3OD): δ 2.62-2.53 (m, 2H), 2.25-2.15 (m, 2H), 2.05-1.97 (m, 2H), 1.42 (s, 9H); ES Mass: 238.04 [M+Na]+.
62.41% With sodium hydroxide In 1,4-dioxane at 0 - 20℃; To a stirred solution of 1-aminocyclobutane-l-carboxylic acid (30 g, 139.53 mmol, 1.0 eq) in 1,4-dioxane (300 ml) at 0 °C was added 2N NaOH solution (300 ml) followed by (Boc)20 (45.62 g, 209.30 mmol, 1.5 eq). The reaction mixture was allowed to stir at room temperature for overnight. TLC indicated starting material was consumed and the desired product was observed. The organic phase was evaporated under reduced pressure, the reaction mixture was diluted with water (50 ml), cooled to 0 °C, pH adjusted to 5 with IN HC1 and then extracted with DCM (3x300 ml). The combined organic extracts were washed with water (300 ml), brine (100 ml) solution, dried over Na2S04, filtered and evaporated under reduced pressure. The residue was stirred with n-hexane (300 ml) at room temperature for about 30 minutes, the obtained solid was filtered and dried under vacuum to give the desired product (35.0 g, yield: 62.41percent) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ ppm 12.19 (brs, 1H), 7.70-7.16 (m, 1H), 2.45-2.36 (m, 2H), 2.12-2.03 (m, 2H), 1.86-1.78 (m, 2H), 1.36 (brs, 9H); ESI-MS: m/z 238.13 (M+Na)+.
19% With sodium hydroxide In tetrahydrofuran; water at 20℃; for 24 h; Stage 1. 1 -[(tert-Butoxycarbonyl)am ino]cyclobutanecarboxyl ic acid To a solution of 1-amino-1-cyclobutane carboxylic acid (2.92 g, 25.4 mmol), NaOH (3.04 g, 76.2 mmol), THF (100 mL) and water (100 mL) at RT was added d-tert-buty dcarbonate (8.30 g, 38.1 rnmoD and the reaction was strred for 24 hrs, The reacUon mixture was acdfled to pH5 usng 2M HC and the mixture was extracted w[th EtOAc (2x 200 mL). The cornbned organcs were dried over MgSO4, ifitered and concentrated in vacuo to give the tWe compound as a whfte sod (1.05 g, 19percent). LCMS: m/z 238 [M+Hj.
1.09 g With sodium hydroxide In methanol; water at 0 - 20℃; for 12 h; Intermediate 68 1-([(1,1-dimethylethyl)oxy]carbonyl}amino)cyclobutanecarboxylic acid [0684] [0685] To a solution of 1-aminocyclobutanecarboxylic acid (626 mg, 5.44 mmol) in 5.6 ml of 1 M aqueous sodium hydroxide and 4 ml of methanol was added Boc-anhydride (1.425 g, 6.53 mmol) at 0° C. The reaction mixture was warmed to room temperature and stirred for 12 hours. After most of the methanol was evaporated, the solution was acidified to pH 2 with 1 M HCl and extracted with ethyl acetate. The organic extracts were combined and washed with brine. Evaporation of the solvent afforded the title compound (1.09 g). [0686] 1H NMR (400 MHz, DMSO-d6): δ ppm 12.21 (1H, s), 7.44 (1H, s), 2.29-2.47 (2H, m), 2.09 (2H, q), 1.74-1.94 (2H, m), 1.36 (9H, s); UPLC: 0.56 min, 216 [M+H]+

Reference: [1] Patent: WO2017/21922, 2017, A1, . Location in patent: Page/Page column 26
[2] Journal of the American Chemical Society, 1997, vol. 119, # 49, p. 11807 - 11816
[3] Patent: WO2016/178092, 2016, A2, . Location in patent: Page/Page column 51; 52
[4] Patent: WO2014/1802, 2014, A1, . Location in patent: Page/Page column 59; 60
[5] Patent: WO2011/69951, 2011, A1, . Location in patent: Page/Page column 79
[6] Patent: WO2011/154677, 2011, A1, . Location in patent: Page/Page column 72
[7] Patent: WO2012/76877, 2012, A1, . Location in patent: Page/Page column 93
[8] Patent: US2013/267510, 2013, A1, . Location in patent: Paragraph 0684-0686
  • 3
  • [ 24424-99-5 ]
  • [ 120728-10-1 ]
Reference: [1] Patent: WO2010/42850, 2010, A1, . Location in patent: Page/Page column 50-51; 66
[2] Patent: WO2011/44498, 2011, A1, . Location in patent: Page/Page column 80
[3] Patent: WO2010/42851, 2010, A1, . Location in patent: Page/Page column 50-51; 66
  • 4
  • [ 163554-54-9 ]
  • [ 120728-10-1 ]
Reference: [1] Synthetic Communications, 2004, vol. 34, # 4, p. 607 - 613
  • 5
  • [ 163554-54-9 ]
  • [ 120728-10-1 ]
YieldReaction ConditionsOperation in experiment
97% With sodium hydroxide In methanol Reference Example F-2
1-tert-Butoxycarbonylaminocyclobutanecarboxylic acid
A 64.28 g (264 mmol) portion of ethyl 1-tert-butoxycarbonylaminocyclobutanecarboxylate was dissolved in 400 ml of methanol, mixed with 400 ml of 1N sodium hydroxide aqueous solution and then stirred overnight at room temperature.
After evaporation of the solvent, the resulting residue was mixed with 20percent citric acid aqueous solution-chloroform.
The resulting organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated to yield 55.29 g (97percent) of the title compound.
1 H-NMR (CDCl3) δ: 1.45 (9H, s), 2.02-2.08 (2H, m), 2.26 (2H, brs), 2.67 (2H, brs), 5.20 (1H, brs).
Reference: [1] Patent: US5849757, 1998, A,
  • 6
  • [ 89691-88-3 ]
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Reference: [1] Journal of the American Chemical Society, 1997, vol. 119, # 49, p. 11807 - 11816
  • 7
  • [ 35120-18-4 ]
  • [ 120728-10-1 ]
Reference: [1] Synthetic Communications, 2004, vol. 34, # 4, p. 607 - 613
  • 8
  • [ 250780-02-0 ]
  • [ 120728-10-1 ]
Reference: [1] Synthetic Communications, 2004, vol. 34, # 4, p. 607 - 613
  • 9
  • [ 24424-99-5 ]
  • [ 120728-10-1 ]
Reference: [1] Synthetic Communications, 2004, vol. 34, # 4, p. 607 - 613
  • 10
  • [ 120728-10-1 ]
  • [ 74-88-4 ]
  • [ 880166-10-9 ]
Reference: [1] Patent: EP1995243, 2008, A1, . Location in patent: Page/Page column 18
  • 11
  • [ 120728-10-1 ]
  • [ 1142211-17-3 ]
Reference: [1] Patent: WO2010/42850, 2010, A1, . Location in patent: Page/Page column 52-53; 67
[2] Patent: WO2011/44501, 2011, A2, . Location in patent: Page/Page column 60; 76
[3] Patent: WO2011/44498, 2011, A1, . Location in patent: Page/Page column 66, 80-81
[4] Patent: WO2011/44538, 2011, A1, . Location in patent: Page/Page column 105-106
[5] Patent: WO2009/67692, 2009, A1, . Location in patent: Page/Page column 187
[6] Patent: WO2010/42851, 2010, A1, . Location in patent: Page/Page column 52-53; 67
[7] Patent: WO2010/132777, 2010, A2, . Location in patent: Page/Page column 195; 48-49
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