Structure of Ac-DL-Abu-OH
CAS No.: 7211-57-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 7211-57-6 |
Formula : | C6H11NO3 |
M.W : | 145.16 |
SMILES Code : | CCC(NC(C)=O)C(O)=O |
MDL No. : | MFCD00020430 |
InChI Key : | WZVZUKROCHDMDT-UHFFFAOYSA-N |
Pubchem ID : | 306107 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.67 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 35.73 |
TPSA ? Topological Polar Surface Area: Calculated from |
66.4 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.09 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.5 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.01 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.16 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.26 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.03 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.16 |
Solubility | 100.0 mg/ml ; 0.69 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.43 |
Solubility | 54.3 mg/ml ; 0.374 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.46 |
Solubility | 50.4 mg/ml ; 0.348 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-7.54 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.56 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.48 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.9% | With acetic acid; at 100℃; for 2.0h; | Example 1A; 2- (Acetylamino) butanoic acid; 163 g (1. 58 mol) 2-Aminobutanoic acid are dissolved in acetic acid, and 242 g (2.37 mol) acetic anhydride are added dropwise. The mixture is stirred for 2 h at 100C until completion of reaction, then the solution is evaporated to dryness in vacuo. The solid residue is suspended in ethyl acetate, filtered and washed with diethyl ether. Yield: 220 g (95.9%) IH-NMR (Methanol-d4): o/ppm 0.97 (t, 3 H), 1.65-1. 93 (m, 2 H), 1.99 (s, 3 H), 4.29 (q, 1 H) ppm. |
95.9% | With acetic acid; at 100℃; for 2.0h; | Example 1A; 2- (Acetylamino) butanoic acid; 163 g (1. 58 mol) 2-Aminobutanoic acid are dissolved in acetic acid, and 242 g (2.37 mol) acetic anhydride are added dropwise. The mixture is stirred for 2 h at 100C until completion of reaction, then the solution is evaporated to dryness in vacuo. The solid residue is suspended in ethyl acetate, filtered and washed with diethyl ether. Yield: 220 g (95.9%) IH-NMR (CD30D) : 6 = 0.97 (t, 3H), 1.65-1. 93 (m, 2H), 1.99 (s, 3H), 4.29 (q, 1H) ppm. |
95.9% | In acetic acid; at 100℃; for 2.0h; | 163 g (1. 58mol) 2-aminobutanoic acid are dissolved in acetic acid, and 242 g (2.37 mol) acetic anhydride are added dropwise. The mixture is stirred for 2 h at 100C until completion of reaction, then the solution is evaporated to dryness in vacuo. The solid residue is suspended in ethyl acetate, filtered and washed with diethyl ether. Yield: 220 g (95.9%) 1H-NMR (Methanol-d4) : 8 = 0.97 (t, 3H), 1.65-1. 93 (m, 2H), 1.99 (s, 3H), 4.29 (q, 1H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 10 A 100 ml stainless steel autoclave was charged with 1.74 g (30 millimoles) of propylene oxide, 3.54 g (60 millimoles) of acetamide, 341 mg (1.0 millimole) of dicobalt octacarbonyl and 568 mg (2.0 millimoles) of titanium tetraisopropoxide as catalysts, and 50 ml of tetrehydrofuran as a solvent, and the mixture was stirred at 110 C. for 12 hours under a carbon monoxide pressure of 50 atmospheres and a hydrogen pressure of 50 atmospheres. After cooling, the pressure of the autoclave was returned to normal atmospheric pressure, and the resulting solution was worked up in the same way as in Example 9 to give 0.80 g (yield 18%) of N-acetyl-alpha-aminobutyric acid having a melting point of 128 to 130 C. as white crystals. The structure of the product was determined from its NMR and infrared absorption spectra. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethanol; | EXAMPLE 2A Ethyl 3-(acetylamino)-2-oxopentanoate 9,2 g (63,4 mmol) 2-(Acetylamino)butanoic acid are suspended in 120 ml tetra-hydrofurane and heated to reflux together with 15,0 g (190 mmol) pyridine and a bit of N,N-dimethylaminopyridine. While heating at reflux, 17,3 g (127 mmol) ethyl chloro(oxo)acetate are added dropwise. The reaction mixture is heated at reflux until no more evolution of gas can be observed. After cooling down to room temperature, the reaction mixture is added to ice water and the organic phase extracted with ethyl acetate. The dried organic phase is evaporated to dryness in vacuo, dissolved in ethanol and the solution directly used for the next reaction. | |
With pyridine; dmap; In tetrahydrofuran;Heating / reflux; | Example 2A; Ethyl 3- (acetylamino)-2-oxop entano ate; 9.2 g (63.4 mmol) 2- (Acetylamino) butanoic acid are suspended in 120 ml tetra- hydrofuran and heated to reflux together with 15.0 g (190 mmol) pyridine and a bit of N, N-dimethylaminopyridine. While heating at reflux, 17. 3 g (127 mmol) ethyl chloro (oxo) acetate are added dropwise. The reaction mixture is heated at reflux until no more evolution of gas can be observed.. After cooling down to room temperature, the reaction mixture is added to ice water and the organic phase extracted with ethyl acetate. The dried organic phase is evaporated to dryness in vacuo, dissolved in ethanol and the solution directly used for the next reaction. | |
With pyridine; dmap; In tetrahydrofuran;Heating / reflux; | Example 2A; Ethyl 3-(acetylamino)-2-oxopentanoate; 9.2 g (63.4 mmol) 2-(Acetylamino) butanoic acid are suspended in 120 ml tetrahydro- furan and heated to reflux together with 15. 0 g (190 mmol) pyridine and a bit of N, N- dimethylaminopyridine. While heating at reflux, 17.3 g (127 mmol) ethyl chloro- (oxo) acetate are added dropwise. The reaction mixture is heated at reflux until no more evolution of gas can be observed. After cooling down to room temperature, the reaction mixture is added to ice water and the organic phase extracted with ethyl acetate. The dried organic phase is evaporated to dryness in vacuo, dissolved in ethanol and the solution directly used for the next reaction. |
With pyridine;dmap; In tetrahydrofuran;Heating / reflux; | 9.2 g (63.4 mmol) 2- (acetylamino) butanoic acid are suspended in 120 ml tetrahydro- furan and heated to reflux together with 15.0 g (190 mmol) pyridine and a bit of N, N- dimethylaminopyridine. While heating at reflux, 17.3 g (127 mmol) ethyl chloro- (oxo) acetate are added dropwise. The reaction mixture is heated at reflux until no more evolution of gas can be observed.. After cooling down to room temperature, the reaction mixture is added to ice water and the organic phase extracted with ethyl acetate. The dried organic phase is evaporated to dryness in vacuo, dissolved in ethanol and the solution directly used for the next reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
220 g (96%) | With acetic anhydride; In acetic acid; ethyl acetate; | EXAMPLE 1A 2-(Acetylamino)butanoic Acid 163 g (1,58 mol) 2-aminobutanoic acid are dissolved in acetic acid, and 242 g (2,37 mol) acetic anhydride are added dropwise. The mixture is stirred for 2 h at 100 C. until completion of reaction, then the solution evaporated to dryness in vacuo. The solid residue is suspended in ethyl acetate, filtered and washed with diethyl ether. Yield: 220 g (96%) 1H-NMR (Methanol-d4): delta=0,97 (t, 3H), 1,65-1,93 (m, 2H), 1,99 (s, 3H), 4,29 (q, 1H) ppm. |
With acetic anhydride; | EXAMPLE 2A 2-(Acetylamino)butanoic acid 163 g (1.58 mol) of 2-aminobutyric acid are reacted analogously to Example 1A with 242 g (2.37 mol) of acetic anhydride to give 2-(acetylamino)butanoic acid. Yield: 220 g (95.9% of th.) 1H-NMR (methanol-d4): delta/ppm 0.97 (t, 3 H), 1.65-1.93 (m, 2 H), 1.99 (s, 3 H), 4.29 (q, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | EXAMPLE VIII Example VII was repeated except that the ethyl 2-acetamido-3-aminobutyrate was replaced with 3.1 g of 2-acetamidobutyric acid. The reaction again resulted in a 95% yield of crystals of 2,3-diaminobutyric acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; | 14.5 g of N-acetyl-DL-2-aminobutyric acid was dissolved in 1 liter of water and the pH thereof was adjusted to 8.0 with LiOH. To the solution were added 83 mg of CoCl2.2H2 O and 21,750 units of a fungal acylase and reacted at 37C. When the L-2-aminobutyric acid produced was followed by a colorimetric determination using ninhydrin, it was found that about 100% conversion was attained in 17 hours. |