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[ CAS No. 149794-10-5 ] {[proInfo.proName]}

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Chemical Structure| 149794-10-5
Chemical Structure| 149794-10-5
Structure of 149794-10-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 149794-10-5 ]

CAS No. :149794-10-5 MDL No. :MFCD00672508
Formula : C9H17NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :SPBIXXXFDSLALC-UHFFFAOYSA-N
M.W :203.24 Pubchem ID :12991451
Synonyms :
Boc-N-Ethylglycine

Calculated chemistry of [ 149794-10-5 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.78
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.76
TPSA : 66.84 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) : -6.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.97
Log Po/w (XLOGP3) : 1.07
Log Po/w (WLOGP) : 1.33
Log Po/w (MLOGP) : 0.83
Log Po/w (SILICOS-IT) : -0.03
Consensus Log Po/w : 1.03

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.38
Solubility : 8.51 mg/ml ; 0.0419 mol/l
Class : Very soluble
Log S (Ali) : -2.07
Solubility : 1.75 mg/ml ; 0.00861 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.69
Solubility : 41.3 mg/ml ; 0.203 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.19

Safety of [ 149794-10-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 149794-10-5 ]

* 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 [ 149794-10-5 ]
  • Downstream synthetic route of [ 149794-10-5 ]

[ 149794-10-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 4530-20-5 ]
  • [ 75-03-6 ]
  • [ 149794-10-5 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 1 h;
Stage #2: at 0℃;
Following the general procedure of Grigg [Blaney, P.; Grigg, R.; Rankovic, Z.; Thornton- Pett, M.; Xu, J. Tetrahedron, 2002, 58, 1719-1737] a roundbottom flask was charged with sodium hydride (480mg 60percent dispersion in oil, 12.0 mmol, 4.0 equiv) and purged with nitrogen for 15 min. THF (6.OmL) was added to the flask, and the suspension was cooled to 0 0C using an ice water bath. A separate flask was charged with BOC-glycine a (525 mg, 3.0 mmol), dry THF (6.0 mL) and ethyl iodide (1.0 mL, 12 mmol, 4 equiv). This mixture was EPO <DP n="134"/>added dropwise to the NaH suspension in THF, with vigorous stirring at 0 0C. After 1 h of stirring, the reaction was warmed to room temperature and allowed to stir overnight. The reaction was again cooled to 0 0C, and methanol (4 mL) was added very slowly to quench the excess hydride. Deionized water was added to dilute the mixture, and methanol was removed under reduced pressure. Impurities were extracted into 90percent ethyl acetate-hexanes, the aqueous layer was then acidified by adding solid citric acid until the pH reached 2-3. The product was extracted into 90percent ethyl acetate-hexanes. This organic layer was dried (Na2SO4) and filtered. Removal of the solvents under reduced pressure afforded a quantitative yield of the product b.
100%
Stage #1: With sodium hydride In tetrahydrofuran at 0 - 20℃;
Stage #2: With citric acid In water
Following the general procedure of Grigg [Blaney, P.; Grigg, R.; Rankovic, Z.; Thornton-Pett, M.; Xu, J. Tetrahedron, 2002, 58, 1719-1737] a roundbottom flask was charged with sodium hydride (480mg 60percent dispersion in oil, 12.0 mmol, 4.0 equiv) and purged with nitrogen for 15 <n="72"/>min. THF (6.OmL) was added to the flask, and the suspension was cooled to 0 °C using an ice water bath. A separate flask was charged with BOC-glycine a (525 mg, 3.0 mmol), dry THF (6.0 mL) and ethyl iodide (1.0 mL, 12 mmol, 4 equiv). This mixture was added dropwise to the NaH suspension in THF, with vigorous stirring at 0 0C. After 1 h of stirring, the reaction was warmed to room temperature and allowed to stir overnight. The reaction was again cooled to 0 0C, and methanol (4 mL) was added very slowly to quench the excess hydride. Deionized water was added to dilute the mixture, and methanol was removed under reduced pressure. Impurities were extracted into 90percent ethyl acetate -hexanes, the aqueous layer was then acidified by adding solid citric acid until the pH reached 2-3. The product was extracted into 90percent ethyl acetate-hexanes. This organic layer was dried (Na2SO4) and filtered. Removal of the solvents under reduced pressure afforded a quantitative yield of the product b.
100%
Stage #1: With sodium hydride In tetrahydrofuran at 0 - 20℃;
Stage #2: With citric acid In water
Example 10 N-Boc-N-methyl-L-glycine; Following the general procedure of Grigg [Blaney, P.; Grigg, R.; Rankovic, Z.; Thornton-Pert, M.; Xu, J. Tetrahedron, 2002, 55, 1719-1737] a roundbottom flask was charged with sodium hydride (480mg 60percent dispersion in oil, 12.0 mmol, 4.0 equiv) and purged with nitrogen for 15 min. THF (6.OmL) was added to the flask, and the suspension was cooled to 0 0C using an ice water bath. A separate flask was charged with BOC-glycine a (525 mg, 3.0 mmol), dry THF (6.0 mL) and ethyl iodide (1.0 mL, 12 mmol, 4 equiv). This mixture was added dropwise to the NaH suspension in THF, with vigorous stirring at 0 °C. After 1 h of stirring, the reaction was warmed to room temperature and allowed to stir overnight. The reaction was again cooled to 0 0C, and methanol (4 mL) was added very slowly to quench the excess hydride. Deionized water was added to dilute the mixture, and methanol was removed under reduced pressure. Impurities were extracted into 90percent ethyl acetate-hexanes, the aqueous layer was then acidified by adding solid citric acid until the pH reached 2-3. The product was extracted into 90percent ethyl acetate-hexanes.This organic layer was dried (Na2SO4) and filtered. Removal of the solvents under reduced pressure afforded a quantitative yield of the product b.
100% With sodium hydride In tetrahydrofuran at 0 - 20℃; Example 29a b c Following the general procedure of Grigg [Blaney, P.; Grigg, R.; Rankovic, Z.; Thornton-Pett, M.; Xu, J. Tetrahedron, 2002, 58, 1719-1737] a roundbottom flask was charged with sodium hydride (480mg 60percent dispersion in oil, 12.0 mmol, 4.0 equiv) and purged with nitrogen for 15 min. THF (6.OmL) was added to the flask, and the suspension was cooled to 0 0C using an ice water bath. A separate flask was charged with BOC-glycine a (525 mg, 3.0 mmol), dry THF (6.0 mL) and ethyl iodide (1.0 mL, 12 mmol, 4 equiv). This mixture was added dropwise to the NaH suspension in THF, with vigorous stirring at 0 0C. After 1 h of stirring, the reaction was warmed to room temperature and allowed to stir overnight. The reaction was again cooled to 0 0C, and methanol (4 mL) was added very slowly to quench the excess hydride. Deionized water was added to dilute the mixture, and methanol was removed under reduced pressure. Impurities were extracted into 90percent ethyl acetate-hexanes, the aqueous layer was then acidified by adding solid citric acid until the pH reached 2-3. The product was extracted into 90percent ethyl acetate-hexanes. This organic layer was dried (Na2SO4) and filtered. Removal of the solvents under reduced pressure afforded a quantitative yield of the product b.

Reference: [1] Patent: WO2006/69063, 2006, A1, . Location in patent: Page/Page column 132-133
[2] Patent: WO2007/106192, 2007, A2, . Location in patent: Page/Page column 70; 71
[3] Patent: WO2008/79735, 2008, A1, . Location in patent: Page/Page column 45
[4] Patent: WO2008/134679, 2008, A1, . Location in patent: Page/Page column 94
[5] Journal of the American Chemical Society, 1993, vol. 115, # 10, p. 4228 - 4245
[6] Patent: WO2010/21934, 2010, A2, . Location in patent: Page/Page column 44
[7] Patent: US2011/46066, 2011, A1,
  • 2
  • [ 627-01-0 ]
  • [ 24424-99-5 ]
  • [ 149794-10-5 ]
YieldReaction ConditionsOperation in experiment
100% With sodium carbonate In 1,2-dimethoxyethane; water for 4 h; 2-[(tert-butoxy)-N-ethylcarbonylamino]acetic Acid A solution of di-tert-butyl dicarbonate (2.18 g, 12.5 mmol) in dimethoxyethane (30 mL) was added to a stirred solution of 2-(ethylamino)acetic acid in Na2CO3 (1.04 g, 10 mmol in water, 30 mL). Stirring was continued for 4 h, then the reaction mixture was acidified with hydrochloric acid (1 N, 30 mL) and extracted with ethyl acetate (3.x.30 mL). The organic layers were dried over Na2SO4 and concentrated in vacuo to give 2-[(tert-butoxy)-N-ethylcarbonylamino]acetic acid as a colorless oil with quantitative yield. 1H NMR (CDCl3), δ 3.95 (m, 2H), 3.30 (m, 2H), 1.45 (m, 9H), 1.12 (t, J=7.2 Hz, 3H).
100% With sodium carbonate In 1,2-dimethoxyethane; water for 4 h; A solution of di-tert-butyl dicarbonate (2.18 g, 12.5 mmol) in dimethoxyethane (30 mL) was added to a stirred solution of 2-(ethylamino)acetic acid in Na2CO3 (1.04 g, 10 mmol in water, 30 mL). Stirring was continued for 4 h, then the reaction mixture was acidified with hydrochloric acid (1 N, 30 mL) and extracted with ethyl acetate (3.x.30 mL). The organic layers were dried over Na2SO4 and concentrated in vacuo to give 2-[(tert-butoxy)-N-ethylcarbonylamino]acetic acid as a colorless oil in quantitative yield. 1H NMR (CDCl3), δ 3.95 (m, 2H), 3.30 (m, 2H), 1.45 (m, 9H), 1.12 (t, J=7.2 Hz, 3H).
Reference: [1] Patent: US2006/79522, 2006, A1, . Location in patent: Page/Page column 12
[2] Patent: US2006/79524, 2006, A1, . Location in patent: Page/Page column 13
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 681 - 695
  • 3
  • [ 4530-20-5 ]
  • [ 75-03-6 ]
  • [ 149794-10-5 ]
YieldReaction ConditionsOperation in experiment
39.9%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.166667 h;
Stage #2: at 60℃; for 10 h;
Stage #3: With citric acid In water; ethyl acetate
General procedure: A suspension of NaH in mineral oil (40 mmol) was added to a stirred solution of Nα-Boc-Nα-alkylamino acid (10 mmol) in anhydrous THF (30 mL), and the mixture was stirred at 20 °C for 10 min. Then alkyl iodide (100 mmol) was added, and the mixture was stirred at 60 °C for 10 h, and maintained at rt overnight. The solvent was removed under vacuum, the residue partitioned in a mixture of ethyl acetate (100 mL) and water (25 mL), and acidified with citric acid to pH 3. The organic phase was separated, washed with saturated aqueous NaCl, containing 1percent of Na2S2O3, and dried over anhydrous MgSO4. After evaporation of ethyl acetate, the residue was loaded on Al2O3 (30 g), and eluted consecutively with heptane (to remove mineral oil), eluent A (for Boc-Xaa-OAlk), and finally, with eluent L (for Boc-Xaa-OH). The fractions were evaporated under vacuum. The traces of acetic acid from eluent L were removed by the azeotrope distillation with toluene under reduced pressure. The products were dried in a desiccator under the residual pressure of 0.13-0.26 kPa.
Reference: [1] Tetrahedron, 2012, vol. 68, # 35, p. 7070 - 7076
  • 4
  • [ 22889-78-7 ]
  • [ 98-80-6 ]
  • [ 950224-92-7 ]
  • [ 149794-10-5 ]
YieldReaction ConditionsOperation in experiment
37% With N2; potassium carbonate In N,N-dimethyl-formamide Example 10
7-phenyl-2-((S)-pyrrolidin-2-yl)thiazolo[5,4-c]pyridine
4-amino-3,5-dichloropyridine a (2.0 g, 12.3 mmol), tetrakis(triphenylphosphine)palladium (696 mg, 0.6 mmol), phenylboronic acid (1.9 g, 15.9 mmol) and potassium carbonate (2.2 g, 15.9 mmol) were mixed in a 10 mL microwave vial under N2 atmosphere. DMF (6 mL) and deoxygenated H2O (1.2 mL) were added.
N2 was bubbled through the mixture for 5 min and the mixture was heated for 20 min at 140° C. in the microwave.
The mixture was diluted with water (30 mL) and extracted with EtOAc (3*20 mL).
The combined organic phases were washed with water (50 mL) and brine (50 mL), dried with MgSO4, filtered and concentrated.
The resulting brown oil was adsorbed on silica gel and purified by flash chromatography (SiO2, 0percent to 70percent ethyl acetate/hexanes) to afford 970 mg (37percent) of b as a colorless oil. MS: m/z=205 (M+H).
Reference: [1] Patent: US2011/46066, 2011, A1,
  • 5
  • [ 24424-99-5 ]
  • [ 623-33-6 ]
  • [ 149794-10-5 ]
Reference: [1] Patent: US2008/125614, 2008, A1,
  • 6
  • [ 24424-99-5 ]
  • [ 149794-10-5 ]
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 25, p. 8579 - 8585
  • 7
  • [ 1249016-05-4 ]
  • [ 149794-10-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 8, p. 2211 - 2214
  • 8
  • [ 6456-74-2 ]
  • [ 149794-10-5 ]
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 25, p. 8579 - 8585
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