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Chemical Structure| 7211-57-6 Chemical Structure| 7211-57-6

Structure of Ac-DL-Abu-OH
CAS No.: 7211-57-6

Chemical Structure| 7211-57-6

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Product Details of [ 7211-57-6 ]

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

Safety of [ 7211-57-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 7211-57-6 ] Show Less

Physicochemical Properties

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
Ertl P. et al. 2000 J. Med. Chem.

66.4 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.09
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.5
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-0.01
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-0.16
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.26
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.03

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.16
Solubility 100.0 mg/ml ; 0.69 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.43
Solubility 54.3 mg/ml ; 0.374 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.46
Solubility 50.4 mg/ml ; 0.348 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

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)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.54 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.56

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.48

Application In Synthesis of [ 7211-57-6 ]

* 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.

  • Downstream synthetic route of [ 7211-57-6 ]

[ 7211-57-6 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 108-24-7 ]
  • [ 2835-81-6 ]
  • [ 7211-57-6 ]
YieldReaction ConditionsOperation 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.
  • 2
  • [ 64-19-7 ]
  • [ 2835-81-6 ]
  • [ 7211-57-6 ]
  • 10
  • [ 692-33-1 ]
  • [ 7211-57-6 ]
  • 11
  • [ 692-33-1 ]
  • [ 7211-57-6 ]
  • [ 13862-98-1 ]
  • 13
  • [ 7211-57-6 ]
  • [ 34271-27-7 ]
  • 14
  • [ 7211-57-6 ]
  • [ 114285-09-5 ]
  • 17
  • [ 60-35-5 ]
  • [ 123-38-6 ]
  • [ 7211-57-6 ]
  • 19
  • [ 7211-57-6 ]
  • N-acetyl-L-2-aminobutyric acid [ No CAS ]
  • 20
  • [ 7211-57-6 ]
  • N-acetyl-D-2-aminobutyric acid [ No CAS ]
  • 21
  • [ 60-35-5 ]
  • [ 201230-82-2 ]
  • [ 75-56-9 ]
  • [ 7211-57-6 ]
YieldReaction ConditionsOperation 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.
  • 23
  • [ 60-35-5 ]
  • [ 123-38-6 ]
  • Co2(CO)8 [ No CAS ]
  • [ 7211-57-6 ]
  • 24
  • [ 2835-81-6 ]
  • usual acetylating agent [ No CAS ]
  • [ 7211-57-6 ]
  • 25
  • [ 7211-57-6 ]
  • 2-acetylamino-butyryl chloride [ No CAS ]
  • 26
  • [ 7211-57-6 ]
  • [ 543-27-1 ]
  • C11H19NO5 [ No CAS ]
  • 27
  • [ 60-35-5 ]
  • [ 201230-82-2 ]
  • [ 123-38-6 ]
  • [ 7211-57-6 ]
  • [ 7073-48-5 ]
  • [ 65693-79-0 ]
  • [ 623-36-9 ]
  • 28
  • [ 7211-57-6 ]
  • 2-acetylamino-<i>N</i>-benzyl-butyramide [ No CAS ]
  • 29
  • [ 7211-57-6 ]
  • N-[1-(4-methylbenzoyl)propyl]acetamide [ No CAS ]
  • 30
  • [ 7211-57-6 ]
  • [ 4755-77-5 ]
  • [ 477902-55-9 ]
YieldReaction ConditionsOperation 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.

  • 31
  • [ 2835-81-6 ]
  • [ 7211-57-6 ]
YieldReaction ConditionsOperation 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).
  • 32
  • [ 7211-57-6 ]
  • [ 2643-66-5 ]
YieldReaction ConditionsOperation 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.
  • 33
  • CoCl2.2H2 O [ No CAS ]
  • [ 7211-57-6 ]
  • [ 2835-81-6 ]
YieldReaction ConditionsOperation 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.
  • 34
  • [ 7211-57-6 ]
  • [ 56-35-9 ]
  • N-acetyl-DL-CH3CHNHCH2COO-tri-n-butyltin [ No CAS ]
  • 35
  • [ 60-35-5 ]
  • [ 201230-82-2 ]
  • [ 123-38-6 ]
  • [ 7211-57-6 ]
 

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