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[ CAS No. 516-06-3 ] {[proInfo.proName]}

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Chemical Structure| 516-06-3
Chemical Structure| 516-06-3
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Product Details of [ 516-06-3 ]

CAS No. :516-06-3 MDL No. :MFCD00004267
Formula : C5H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 117.15 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 516-06-3 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 30.63
TPSA : 63.32 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) : -8.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.03
Log Po/w (XLOGP3) : -2.26
Log Po/w (WLOGP) : 0.05
Log Po/w (MLOGP) : -2.2
Log Po/w (SILICOS-IT) : -0.54
Consensus Log Po/w : -0.78

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.99
Solubility : 1140.0 mg/ml ; 9.76 mol/l
Class : Highly soluble
Log S (Ali) : 1.46
Solubility : 3410.0 mg/ml ; 29.1 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.29
Solubility : 227.0 mg/ml ; 1.94 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.19

Safety of [ 516-06-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 516-06-3 ]

* 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 [ 516-06-3 ]
  • Downstream synthetic route of [ 516-06-3 ]

[ 516-06-3 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 516-06-3 ]
  • [ 16935-34-5 ]
Reference: [1] Synlett, 2018, vol. 29, # 7, p. 943 - 948
  • 2
  • [ 98-88-4 ]
  • [ 516-06-3 ]
  • [ 2901-80-6 ]
YieldReaction ConditionsOperation in experiment
95% With sodium hydroxide In water Step A:
N-Benzoylvaline
Dissolve 0.1 mol (11.7 g) of valine in 50 ml of water, add 0.25 mol of sodium hydroxide in aqueous solution, heat to 30° C. and then add dropwise 0.15 mol (17.5 ml) of benzoyl chloride.
Wash the aqueous solution with ether, acidify and suction off the N-benzoylvaline crystals.
Melting point: 125° C.
Yield: 95percent
83%
Stage #1: With sodium hydroxide In water at 20℃; for 0.5 h;
Stage #2: With sodium hydroxide In water at 0 - 20℃; for 3 h;
A solution of 2-amino-3-methylbutanoic acid (500 mg, 4.27 mmol) in 2N NaOH (2.35 ml, 4.69 mmol) was stirred at RT for 30 minutes, then the reaction mixture was cooled at 0°C and benzoyl chloride (471 μ, 4.05 mmol) and 2N NaOH (2.35 ml, 4.69 mmol) were simultaneously added dropwise from two different syringes. The reaction was stirred at RT for 3h. Water was added, the aqueous phase was washed with Et2O, then acidified with 1M HCl and back-extracted with Et2O, dried over Na2SO4 and evaporated. The residue was triturated with z-Pr2O to obtain 2-benzamido-3-methylbutanoic acid (780 mg, 83percent yield).
83% at 0 - 20℃; for 3.5 h; A solution of 2-amino-3-methylbutanoic acid (500 mg, 4.27 mmol) in 2N NaOH (2.35 ml, 4.69 mmol) was stirred at RT for 30 minutes, then the reaction mixture was cooled at 0° C., and benzoyl chloride (471 μl, 4.05 mmol) and 2N NaOH (2.35 ml, 4.69 mmol) were simultaneously added dropwise from two different syringes. The reaction was stirred at RT for 3 hours. Water was added, the aqueous phase was washed with Et2O, then acidified with 1M HCl and back-extracted with Et2O, dried over Na2SO4 and evaporated. The residue was triturated with i-Pr2O to obtain 2-benzamido-3-methylbutanoic acid (780 mg, 83percent yield).
Reference: [1] Patent: US5254548, 1993, A,
[2] Journal of the American Chemical Society, 2014, vol. 136, # 51, p. 17869 - 17881
[3] Organic Letters, 2018, vol. 20, # 22, p. 7239 - 7244
[4] Patent: WO2012/69275, 2012, A1, . Location in patent: Page/Page column 118
[5] Patent: US2012/134934, 2012, A1, . Location in patent: Page/Page column 59-60
[6] European Journal of Organic Chemistry, 2009, # 3, p. 378 - 386
[7] Journal of Organic Chemistry, 2014, vol. 79, # 4, p. 1542 - 1554
[8] Journal of Biological Chemistry, 1941, vol. 138, p. 627
[9] Chemische Berichte, 1902, vol. 35, p. 409
[10] Russian Journal of Organic Chemistry, 1994, vol. 30, # 5.2, p. 767 - 770[11] Zhurnal Organicheskoi Khimii, 1994, vol. 30, # 5, p. 723 - 725
[12] Australian Journal of Chemistry, 1976, vol. 29, p. 339 - 356
[13] Tetrahedron Letters, 1986, vol. 27, # 14, p. 1579 - 1582
[14] Monatshefte fur Chemie, 2000, vol. 131, # 6, p. 667 - 672
[15] Revue Roumaine de Chimie, 1999, vol. 44, # 2, p. 137 - 142
[16] Journal of Organic Chemistry, 2002, vol. 67, # 18, p. 6542 - 6545
[17] Patent: US5091378, 1992, A,
[18] Journal of Chemical Research, 2011, vol. 35, # 8, p. 468 - 470
[19] Journal of Organic Chemistry, 2017, vol. 82, # 1, p. 126 - 134
  • 3
  • [ 959-22-8 ]
  • [ 516-06-3 ]
  • [ 2901-80-6 ]
Reference: [1] Russian Journal of General Chemistry, 2018, vol. 88, # 1, p. 80 - 85[2] Zh. Obshch. Khim., 2018, vol. 88, # 1, p. 84 - 89,6
  • 4
  • [ 516-06-3 ]
  • [ 16369-05-4 ]
Reference: [1] Synthetic Communications, 2000, vol. 30, # 23, p. 4387 - 4395
[2] Analytical Chemistry, 2001, vol. 73, # 4, p. 799 - 802
[3] Journal of Organic Chemistry, 1962, vol. 27, p. 1049
[4] Journal of Organic Chemistry, 1990, vol. 55, # 11, p. 3464 - 3474
[5] Journal of medicinal chemistry, 1966, vol. 9, # 6, p. 911 - 920
[6] Patent: US2003/153771, 2003, A1,
[7] Synlett, 2008, # 12, p. 1829 - 1832
[8] Patent: WO2017/176960, 2017, A1, . Location in patent: Paragraph 00779
  • 5
  • [ 13292-87-0 ]
  • [ 516-06-3 ]
  • [ 16369-05-4 ]
YieldReaction ConditionsOperation in experiment
62% With sodium hydroxide In tetrahydrofuran; water EXAMPLE 2
A dry, 12-liter glass reaction vessel equipped as described in Example 1 was charged with 900 grams (7.7 moles) of valine and 2.5 liters of tetrahydrofuran.
Using the procedure described in Example 1, boron trifluoride diethyl etherate (1.05 liters, 8.5 moles) was added followed by 0.85 liter (8.5 moles) of borane-dimethyl sulfide at reflux.
The addition took 8 hours and heating was continued for an additional 3 hours following the addition.
The reaction mixture was then hydrolyzed with 0.75 liter of tetrahydrofuran/water followed by 24.6 moles of sodium hydroxide as an aqueous solution.
The product was isolated as described in Example 1 giving 494 grams (62percent yield) of 2-amino-3-methyl-1-butanol, bp 78°-79°C at 8 mm, n20D 1.4543, purity by glc analysis: 97percent.
Reference: [1] Patent: US3935280, 1976, A,
  • 6
  • [ 67-56-1 ]
  • [ 516-06-3 ]
  • [ 5619-05-6 ]
Reference: [1] Russian Journal of General Chemistry, 2007, vol. 77, # 4, p. 581 - 585
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 259 - 264
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 265 - 268
[4] Russian Journal of General Chemistry, 1999, vol. 69, # 11, p. 1846 - 1847[5] Zhurnal Obshchei Khimii, 1999, vol. 69, # 11, p. 1929 - 1930
[6] Farmaco (Societa chimica italiana : 1989), 2001, vol. 56, # 12, p. 929 - 931
[7] Angewandte Chemie - International Edition, 2004, vol. 43, # 48, p. 6695 - 6699
[8] Journal of Organic Chemistry, 2008, vol. 73, # 7, p. 2784 - 2791
[9] Tetrahedron Letters, 2008, vol. 49, # 24, p. 3943 - 3945
[10] Synthetic Communications, 2010, vol. 40, # 8, p. 1161 - 1179
[11] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 2, p. 406 - 409
[12] Chemical Communications, 2012, vol. 48, # 10, p. 1443 - 1445
[13] Green Chemistry, 2012, vol. 14, # 5, p. 1350 - 1356
[14] European Journal of Organic Chemistry, 2013, # 24, p. 5398 - 5413
[15] Journal of the American Chemical Society, 2016, vol. 138, # 1, p. 265 - 271
[16] Russian Chemical Bulletin, 2017, vol. 66, # 1, p. 136 - 142[17] Izv. Akad. Nauk, Ser. Khim., 2017, # 1, p. 136 - 142,6
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