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[ CAS No. 167216-17-3 ] {[proInfo.proName]}

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Chemical Structure| 167216-17-3
Chemical Structure| 167216-17-3
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Product Details of [ 167216-17-3 ]

CAS No. :167216-17-3 MDL No. :MFCD18831346
Formula : C9H19NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :JSZOAOLSEKSNTD-SSDOTTSWSA-N
M.W : 189.25 Pubchem ID :29928104
Synonyms :

Calculated chemistry of [ 167216-17-3 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.89
Num. rotatable bonds : 6
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 51.05
TPSA : 58.56 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) : -6.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.18
Log Po/w (XLOGP3) : 1.03
Log Po/w (WLOGP) : 1.28
Log Po/w (MLOGP) : 0.95
Log Po/w (SILICOS-IT) : 0.62
Consensus Log Po/w : 1.21

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.27
Solubility : 10.3 mg/ml ; 0.0542 mol/l
Class : Very soluble
Log S (Ali) : -1.85
Solubility : 2.67 mg/ml ; 0.0141 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.5
Solubility : 5.93 mg/ml ; 0.0313 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.57

Safety of [ 167216-17-3 ]

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 [ 167216-17-3 ]

* 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 [ 167216-17-3 ]
  • Downstream synthetic route of [ 167216-17-3 ]

[ 167216-17-3 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 167216-17-3 ]
  • [ 61477-40-5 ]
YieldReaction ConditionsOperation in experiment
95.8% With trifluoroacetic acid In dichloromethane at 0 - 10℃; The compound of formula II (65 g) was dissolved in 510 mL of methylene chloride and cooled to 0 to 10 ° C. 47 g of trifluoroacetic acid was slowly added dropwise to the system. The temperature was kept until the conversion of the raw material was completed. Sodium hydroxide solid , The system pH adjusted to 9 ~ 10, too Filtration, concentration and distillation gave 29.3 g of (R) -3-aminobutanol, yield 95.8percent
90% With hydrogenchloride In methanol; water at 25℃; for 6 h; Green chemistry Take 50g N-Boc-(R)-3-aminobutanol, dissolved in 350mL of concentrated hydrochloric acid / methanol system, the reaction for 6 hours at 25 °C, the GC detects completion of the reaction starting material, 54g of potassium carbonate was added, stirred for 1 hour, filtered The filtrate was concentrated and distilled under reduced pressure to give a product,m.p., 21 g, yield: 90percent, purity 99percent, ee.
0.5 g With hydrogenchloride In methanol at 25℃; To a solution of (R)-tert-butyl(4-hydroxybutan-2-yl) carbamate (1.3 g, 6.87 mmol) in methanol (30 mL) was added HC1 (30 mL, 4M in MeOH), stirred at 25°C overnight, concentrated to afford the title compound (0.5 g).
Reference: [1] Patent: CN106966912, 2017, A, . Location in patent: Paragraph 0025
[2] Patent: CN108424370, 2018, A, . Location in patent: Paragraph 0093; 0094
[3] Patent: WO2014/114249, 2014, A1, . Location in patent: Page/Page column 21
  • 2
  • [ 167216-17-3 ]
  • [ 497861-77-5 ]
Reference: [1] Chemistry - A European Journal, 2009, vol. 15, # 40, p. 10514 - 10532
[2] Chemistry - A European Journal, 2009, vol. 15, # 9, p. 2050 - 2054
  • 3
  • [ 159877-47-1 ]
  • [ 167216-17-3 ]
YieldReaction ConditionsOperation in experiment
1.3 g
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at -78℃; for 1 h; Inert atmosphere
Stage #2: With sodium hydroxide In water at 20℃; for 1 h;
To a solution of (R)-3-((tert-butoxycarbonyl)amino)butanoate (3.0 g, 14.76 mmol) in tetrahydrofuran (THF) (50 mL) was added aluminum(III) lithium hydride (0.728 g, 19.19 mmol), stirred at -78 °C for 1 h under nitrogen. The reaction mixture was warmed to 0°C, quenched by addition of H20 (0.7 mL) and aq. 15percent NaOH (0.7 mL), stirred for 1 h at r.t, filtered through celite, dried over Na2S04, concentrated to afford the title compound (1.3 g).
Reference: [1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 1, p. 92 - 96
[2] Patent: US2011/237814, 2011, A1, . Location in patent: Page/Page column 11
[3] Patent: WO2014/114249, 2014, A1, . Location in patent: Page/Page column 21
  • 4
  • [ 159991-23-8 ]
  • [ 167216-17-3 ]
YieldReaction ConditionsOperation in experiment
95% With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at -20℃; Green chemistry 100 g of N-Boc-(R)-3-aminobutyric acid and 300 mL of tetrahydrofuran were placed in a reaction flask, 20.6 g of sodium borohydride was added in portions, the temperature was lowered to -20 °C, and 100 g of boron trifluoride etherate was slowly added dropwise. HPLC to determine whether the raw material reaction is complete. After completion of the reaction, the reaction was quenched by the addition of methanol, and the solvent was evaporated. Filter to remove solids,The filtrate was washed with 100 ml of saturated sodium bicarbonate.The organic phase was concentrated to give N-Boc-(R)-3-aminobutanol as a white solid, 88 g, yield 95percent, mp. 99.0percent (HPLC method).
91% With sodium tetrahydroborate; iodine In tetrahydrofuran at 0 - 30℃; 115 g of the compound of formula I was dissolved in 460 mL of tetrahydrofuran, cooled to 0~10 ° C. in an ice bath, 23.7 g of sodium borohydride was added in portions, the temperature was controlled at 0~10 ° C., and 165.4 g of elemental iodine Of 230 mL of tetrahydrofuran solution, the dropwise addition, and gradually warmed to 25 ~ 30 ° C,Liquid phase tracking is complete until the conversion of the raw material, 60 mL of water is added dropwise to quench the reaction, concentrated under reduced pressure to no distillate, 500 mL of methanol is added, the temperature is raised to 55-60 ° C., the solution is incubated for 0.5 h, mL water, drops After completion of the incubation, the mixture was stirred for 1 hour, then slowly cooled to 15-20 ° C, filtered and dried to obtain 97.4 g of the compound of formula II in a yield of 91percent.
Reference: [1] Patent: CN108424370, 2018, A, . Location in patent: Paragraph 0090; 0091
[2] Patent: CN106966912, 2017, A, . Location in patent: Paragraph 0022; 0023; 0024
  • 5
  • [ 24424-99-5 ]
  • [ 61477-40-5 ]
  • [ 167216-17-3 ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine In dichloromethane at 20 - 24℃; for 4 h; Example 36
Preparation of (R)-tert-butyl(4-hydroxybutan-2-yl)carbamate (C56)
Triethylamine (2.35 mL, 16.8 mmol) and di-tert-butyl dicarbonate (2.50 g, 12.3 mmol) were added to a solution of (R)-3-aminobutan-1-ol (1.00 g, 11.2 mmol) in dichloromethane (10 mL).
The reaction mixture was stirred for 4 hours at room temperature.
The reaction mixture was concentrated, the residue poured into ice water, and then extracted with ethyl acetate.
The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated.
Purification by flash column chromatography using 20percent ethyl acetate/petroleum ether as eluent provided the title compound as a white solid (1.7 g, 80percent): 1H NMR (400 MHz, DMSO-d6) δ 6.62 (d, J=8.4 Hz, 1H), 4.43-4.31 (m, 1H), 3.55-3.52 (m, 1H), 3.40-3.38 (m, 2H), 1.55-1.48 (m, 2H), 1.43 (s, 9H), 1.01 (d, J=6.8 Hz, 3H).
Reference: [1] Patent: US2017/210723, 2017, A1, . Location in patent: Paragraph 0537-0538
  • 6
  • [ 161529-22-2 ]
  • [ 167216-17-3 ]
Reference: [1] Patent: WO2005/26113, 2005, A1, . Location in patent: Page 32-33
  • 7
  • [ 1047665-48-4 ]
  • [ 167216-17-3 ]
Reference: [1] Chemistry - A European Journal, 2009, vol. 15, # 9, p. 2050 - 2054
[2] Chemistry - A European Journal, 2009, vol. 15, # 40, p. 10514 - 10532
  • 8
  • [ 24424-99-5 ]
  • [ 167216-17-3 ]
Reference: [1] Patent: WO2014/114249, 2014, A1,
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