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[ CAS No. 543-24-8 ] {[proInfo.proName]}

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Chemical Structure| 543-24-8
Chemical Structure| 543-24-8
Structure of 543-24-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 543-24-8 ]

CAS No. :543-24-8 MDL No. :MFCD00004275
Formula : C4H7NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :OKJIRPAQVSHGFK-UHFFFAOYSA-N
M.W : 117.10 Pubchem ID :10972
Synonyms :
Aceturic acid;Acetamidoacetic acid;NSC 7605;NAGly
Chemical Name :Ac-Gly-OH

Calculated chemistry of [ 543-24-8 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 26.12
TPSA : 66.4 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) : -7.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.67
Log Po/w (XLOGP3) : -1.18
Log Po/w (WLOGP) : -0.79
Log Po/w (MLOGP) : -0.95
Log Po/w (SILICOS-IT) : -0.8
Consensus Log Po/w : -0.61

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : 0.38
Solubility : 278.0 mg/ml ; 2.37 mol/l
Class : Highly soluble
Log S (Ali) : 0.28
Solubility : 223.0 mg/ml ; 1.9 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.01
Solubility : 119.0 mg/ml ; 1.02 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 543-24-8 ]

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 [ 543-24-8 ]

* 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 [ 543-24-8 ]
  • Downstream synthetic route of [ 543-24-8 ]

[ 543-24-8 ] Synthesis Path-Upstream   1~8

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Reference: [1] Patent: WO2006/138350, 2006, A2, . Location in patent: Page/Page column 79
  • 2
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  • [ 543-24-8 ]
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  • 3
  • [ 543-24-8 ]
  • [ 95-01-2 ]
  • [ 79418-41-0 ]
Reference: [1] Angewandte Chemie, International Edition, 2009, vol. 48, p. 4034 - 4037[2] Angewandte Chemie, 2009, vol. 121, p. 4094 - 4097
[3] Tetrahedron Letters, 2012, vol. 53, # 39, p. 5280 - 5283
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[6] Patent: CN105693674, 2016, A, . Location in patent: Paragraph 0024
[7] Chemical Communications, 2017, vol. 53, # 25, p. 3583 - 3586
  • 4
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  • [ 881-90-3 ]
YieldReaction ConditionsOperation in experiment
100% With sodium acetate In acetic anhydride at 120℃; for 7 h; General procedure: A mixture of aromatic aldehyde (100 mmol), N-acylglycine (10.7 g, 120 mmol), sodium acetate (51 g, 500 mmol) were mixed and heated at 120 °C for 7 h. After completion of the reaction, the resulting solution was kept in refrigerator overnight to obtain a solidified mass which was triturated with cold water and ethanol. The resulting yellow crystals were collect and dried to give 4-(arylmethylene)-2-methyl-5(4H)-oxazolone (2).
74.25% Heating General procedure: A mixture of aldehyde (1 mol), acetyl glycine (1, 1 mol), acetic anhydride (3 mol) and anhydrous potassium acetate (1 mol) was heated on an electric hot plate with constant shaking till the mixture liquefied. Then the content of RBF was further heated on water bath for 2 h. To this, 100 mL of ethanol was added slowly and allowed the mixture to stand overnight. The crystalline product was separated by filtration, washed with 25 mL of ice-cold alcohol and then finally washed with 25 mL of boiling water and recrystallized using suitable solvent.
70% at 160℃; for 1 h; N-Acetylglycine (0.80g,6.80mmol), benzaldehyde (1.08g, 10.20mmol) and sodium acetate(0.41g, 0.50mmol) were added to a round-bottomed flask. To this mixture wascarefully added acetic anhydride (1.73g, 1.6mL, 17.00mmol). The mixture washeated at 160°C under stirring for 1 h. The resulting solution was cooled atroom temperature and stored in fridge at 2-4°C for 24 h. The mixture was washedwith cold water, filtered, washed again with cold water and small amount of Et2O(x2)and dried to afford the desired product.
38% at 95 - 135℃; for 4 h; General procedure: To a solution of N-acylglycine in acetic anhydride (reaction concentration=1 M) was added sodium acetate (0.63 equiv) and aryl-aldehyde (1.25 equiv) at room temperature. The reaction mixture was heated at 95-135 °C for the specific time (monitored by TLC). Ice was added to the reaction mixture and the resulting solution was cooled to 0 °C overnight. The precipitate was collected by filtration and the solid was recrylstallized to give the product. Alternatively, the aqueous solution was extracted by CHCl3 and the product was purified by flash column chromatography.
32% for 1 h; Reflux 4-Benzylidene-2-methyloxazol-5(4H)-one synthesis: To a suspension of 25 acetylglycine (5.86 g, 50 mmol), 26 sodium acetate (4.10 g, 50 mmol), in 27 acetic anhydride (47.3 mL, 500 mmol), was added 28 benzaldehyde (5.11 mL, 50 mmol). The reaction mixture was heated in a 100 C oil bath for 10 min to dissolve. A reflux condenser was then added and the bath heated to 140 C for exactly 1 h. The reaction flask was then plunged into an ice-water bath with stirring and allowed to stir for 1 h. After 1 h, ice cold 29 water (47 mL) was added to the suspension of yellow solid in a dark red solution. The product was collected on a fritted glass funnel, washed with ice cold water (3×50 mL) with stirring in the funnel. The crude product was dried in a desiccators over solid 30 KOH overnight to provide 4.6 g of product as a yellow powder. This material was recrystallized from 85 mL of hot 2-propanol, cooling slowly to room temp, chilled in an ice bath, and then collected by filtration to provide 2.98 g, 32percent yield of purified 31 4-benzylidene-2-methyloxazol-5(4H)-one: mp 148-151 C.

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  • 5
  • [ 127-09-3 ]
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  • 6
  • [ 104-87-0 ]
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  • [ 93634-54-9 ]
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  • [ 556-50-3 ]
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  • 8
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  • [ 22356-89-4 ]
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