Home Cart Sign in  
Chemical Structure| 57113-90-3 Chemical Structure| 57113-90-3

Structure of 57113-90-3

Chemical Structure| 57113-90-3

Methyl 2-((tert-butoxycarbonyl)amino)-3-nitrobenzoate

CAS No.: 57113-90-3

4.5 *For Research Use Only !

Cat. No.: A235587 Purity: 98%

Change View

Size Price

US Stock

Global Stock

In Stock
1g łËÿ¶ÊÊ Inquiry Inquiry
5g łòî¶ÊÊ Inquiry Inquiry
25g łËÊò¶ÊÊ Inquiry Inquiry
100g łďî§¶ÊÊ Inquiry Inquiry

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • 1g

    łËÿ¶ÊÊ

  • 5g

    łòî¶ÊÊ

  • 25g

    łËÊò¶ÊÊ

  • 100g

    łďî§¶ÊÊ

In Stock

- +

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 57113-90-3 ]

CAS No. :57113-90-3
Formula : C13H16N2O6
M.W : 296.28
SMILES Code : O=C(OC)C1=CC=CC([N+]([O-])=O)=C1NC(OC(C)(C)C)=O
MDL No. :MFCD06797690
Boiling Point : No data available
InChI Key :VEDIIGMQOAWKGH-UHFFFAOYSA-N
Pubchem ID :9965968

Safety of [ 57113-90-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 57113-90-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 21
Num. arom. heavy atoms 6
Fraction Csp3 0.38
Num. rotatable bonds 7
Num. H-bond acceptors 6.0
Num. H-bond donors 1.0
Molar Refractivity 76.79
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

110.45 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.77
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

2.72
Log Po/w (WLOGP)?

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

2.54
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.

1.31
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

-0.38
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.79

Water Solubility

Log S (ESOL):?

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

-3.14
Solubility 0.215 mg/ml ; 0.000725 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-4.69
Solubility 0.006 mg/ml ; 0.0000203 mol/l
Class?

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

Moderately 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

-2.8
Solubility 0.474 mg/ml ; 0.0016 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

Yes
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

Yes
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.

-6.18 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

0.0
Bioavailability Score?

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

0.55

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

3.0 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<0.0
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)

3.02

Application In Synthesis of [ 57113-90-3 ]

* 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.

  • Downstream synthetic route of [ 57113-90-3 ]

[ 57113-90-3 ] Synthesis Path-Downstream   1~37

  • 1
  • [ 57113-90-3 ]
  • [ 114772-54-2 ]
  • [ 139481-38-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In acetonitrile; at 80 - 85℃; for 5h;Heating / reflux; Industry scale; methyl 2-t-butoxycarbonylamino-3-nitrobenzoate [BAN] obtained in Reference Example 3 (354 kg), a solution of 4-(2-bromomethylphenyl)benzonitrile [BMB] in acetonitrile obtained in Reference Example 4 (1), and anhydrous potassium carbonate (475 kg) were added to acetonitrile (1600 kg), and the mixture was heated (80 to 85 C) under reflux for about 5 hours.. The reaction solution was cooled, and the insoluble were separated and washed with acetonitrile (320 kg).. The filtrated washing was concentrated under reduced pressure to give concentrate of methyl 2-[N-t-butoxycarbonyl-N-[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate [BBN].
  • 2
  • [ 57113-90-3 ]
  • [ 114772-38-2 ]
  • [ 150058-11-0 ]
  • 4
  • [ 57113-90-3 ]
  • [ 169270-61-5 ]
  • [ 169270-79-5 ]
  • 5
  • [ 57113-90-3 ]
  • [ 169270-73-9 ]
  • [ 1028312-00-6 ]
YieldReaction ConditionsOperation in experiment
86.7% Reference Example 2 Production of methyl 2-t-butoxycarbonylamino-3-nitrobenzoate [BAN] In dimethylformamide [DMF] (242 kg) was dissolved methyl 2-carboxy-3-nitrobenzoate [MNA] (164 kg) obtained in Reference Example 1. To the solution was dropped diphenylphosphorylazide [DPPA] (204 kg) at room temperature and then triethylamine (87 kg) at the temperature ranging 20-35 C. After the solution was stirred at 20-30 C. for about 3 hours, t-butylalcohol (930 kg) was added to the reaction solution. The solution was heated for 3-5 hours to 85-90 C. and then stirred for 1-2 hours under reflux (85-90 C.). The reaction solution was cooled, concentrated and dissolved in ethyl acetate(1400 L). The solution was washed with a mixture of 15% hydrochloric acid (160 L) and water (1890 L), water (660 L), 5% solution of sodium bicarbonate (1100 kg), and water (660 L), in this order and the organic layer was concentrated under reduced pressure. To the concentrate was added methanol (300 kg) and then were added crystal seeds (15 kg) and methanol (450 kg). The solution was heated to 50-60 C. to dissolve insoluble materials. The solution was cooled to 5 C. and precipitated crystals were separated. The crystals were washed with cooled methanol (100 L) and dried to give methyl 2-t-butoxycarbonylamino-3-nitrobenzoate [BAN] (187.0 kg, 86.7%). Mother liquor and the methanol solution used for washing the crystals was concentrated under reduced pressure and cooled. The precipitated crystals were centrifuged, washed with cooled methanol and dried to obtain the second crystals of BAN. 1H-NMR (200 MHz, CDCl3) delta: 1.50 (9H, s), 3.96 (3H, s), 7.23 (1H, t), 8.10 (1H, dd), 8.17 (1H, dd) IR (KBr) cm-1: 3360, 1730, 1705, 1580, 1520, 1490, 1440, 1365, 1355, 1310, 1270, 1240, 1150, 870, 835, 770, 725, 705
  • 8
  • [ 73833-13-3 ]
  • [ 57113-90-3 ]
  • 11
  • [ 57113-90-3 ]
  • [ 136285-69-3 ]
  • 12
  • [ 57113-90-3 ]
  • [ 139481-37-1 ]
  • 13
  • [ 57113-90-3 ]
  • [ 139481-28-0 ]
  • 14
  • [ 57113-90-3 ]
  • [ 139481-33-7 ]
  • 15
  • [ 57113-90-3 ]
  • [ 139481-34-8 ]
  • 16
  • [ 57113-90-3 ]
  • [ 136304-69-3 ]
  • 17
  • [ 57113-90-3 ]
  • 1-<(2'-cyanobiphenyl-4-yl)methyl>-2-<(methylthio)methyl>-1H-benzimidazole-7-carboxylic acid [ No CAS ]
  • 18
  • [ 57113-90-3 ]
  • [ 139481-47-3 ]
  • 19
  • [ 57113-90-3 ]
  • [ 139481-48-4 ]
  • 20
  • [ 57113-90-3 ]
  • [ 139481-43-9 ]
  • 21
  • [ 57113-90-3 ]
  • [ 139481-36-0 ]
  • 22
  • [ 57113-90-3 ]
  • [ 139481-35-9 ]
  • 23
  • [ 57113-90-3 ]
  • [ 139481-31-5 ]
  • 24
  • [ 57113-90-3 ]
  • [ 136285-43-3 ]
  • 25
  • [ 57113-90-3 ]
  • [ 136304-70-6 ]
  • 26
  • [ 57113-90-3 ]
  • [ 147404-04-4 ]
  • 27
  • [ 57113-90-3 ]
  • [ 150058-13-2 ]
  • 28
  • [ 57113-90-3 ]
  • [ 136304-81-9 ]
  • 29
  • [ 57113-90-3 ]
  • [ 139481-44-0 ]
  • 30
  • [ 57113-90-3 ]
  • [ 139481-56-4 ]
  • 31
  • [ 57113-90-3 ]
  • [ 136304-79-5 ]
  • 32
  • [ 57113-90-3 ]
  • [ 139481-55-3 ]
  • 33
  • [ 57113-90-3 ]
  • [ 150058-16-5 ]
  • 34
  • [ 57113-90-3 ]
  • [ 139481-50-8 ]
  • 35
  • [ 57113-90-3 ]
  • 3-(2'-Carboxy-biphenyl-4-ylmethyl)-2-ethoxy-3H-benzoimidazole-4-carboxylic acid [ No CAS ]
  • 36
  • [ 57113-90-3 ]
  • 2-Methyl-3-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-benzoimidazole-4-carboxylic acid [ No CAS ]
  • 37
  • [ 57113-90-3 ]
  • [ 136304-71-7 ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 57113-90-3 ]

Aryls

Chemical Structure| 669713-59-1

A232746 [669713-59-1]

2-tert-Butoxycarbonylamino-3-methylbenzoic acid

Similarity: 0.79

Chemical Structure| 231958-04-6

A129765 [231958-04-6]

3-((tert-Butoxycarbonyl)amino)-4-methylbenzoic acid

Similarity: 0.79

Chemical Structure| 180976-94-7

A273533 [180976-94-7]

4-((tert-Butoxycarbonyl)amino)-3-methylbenzoic acid

Similarity: 0.78

Chemical Structure| 7356-52-7

A118079 [7356-52-7]

3-Acetamido-4-methyl-2-nitrobenzoic acid

Similarity: 0.77

Chemical Structure| 1588441-20-6

A125012 [1588441-20-6]

tert-Butyl (2-methyl-3,5-dinitrophenyl)carbamate

Similarity: 0.77

Amides

Chemical Structure| 4693-02-1

A262454 [4693-02-1]

6-Nitro-1H-benzo[d][1,3]oxazine-2,4-dione

Similarity: 0.82

Chemical Structure| 63480-10-4

A281431 [63480-10-4]

7-Nitro-1H-benzo[d][1,3]oxazine-2,4-dione

Similarity: 0.81

Chemical Structure| 669713-59-1

A232746 [669713-59-1]

2-tert-Butoxycarbonylamino-3-methylbenzoic acid

Similarity: 0.79

Chemical Structure| 231958-04-6

A129765 [231958-04-6]

3-((tert-Butoxycarbonyl)amino)-4-methylbenzoic acid

Similarity: 0.79

Chemical Structure| 180976-94-7

A273533 [180976-94-7]

4-((tert-Butoxycarbonyl)amino)-3-methylbenzoic acid

Similarity: 0.78

Esters

Chemical Structure| 4693-02-1

A262454 [4693-02-1]

6-Nitro-1H-benzo[d][1,3]oxazine-2,4-dione

Similarity: 0.82

Chemical Structure| 63480-10-4

A281431 [63480-10-4]

7-Nitro-1H-benzo[d][1,3]oxazine-2,4-dione

Similarity: 0.81

Chemical Structure| 354587-63-6

A120966 [354587-63-6]

1-tert-Butyl 6-methyl 1H-indole-1,6-dicarboxylate

Similarity: 0.76

Chemical Structure| 57113-91-4

A104712 [57113-91-4]

Methyl 2-amino-3-nitrobenzoate

Similarity: 0.75

Chemical Structure| 193014-01-6

A115984 [193014-01-6]

Ethyl 3-amino-2-nitrobenzoate

Similarity: 0.75

Amines

Chemical Structure| 669713-59-1

A232746 [669713-59-1]

2-tert-Butoxycarbonylamino-3-methylbenzoic acid

Similarity: 0.79

Chemical Structure| 231958-04-6

A129765 [231958-04-6]

3-((tert-Butoxycarbonyl)amino)-4-methylbenzoic acid

Similarity: 0.79

Chemical Structure| 180976-94-7

A273533 [180976-94-7]

4-((tert-Butoxycarbonyl)amino)-3-methylbenzoic acid

Similarity: 0.78

Chemical Structure| 7356-52-7

A118079 [7356-52-7]

3-Acetamido-4-methyl-2-nitrobenzoic acid

Similarity: 0.77

Chemical Structure| 1588441-20-6

A125012 [1588441-20-6]

tert-Butyl (2-methyl-3,5-dinitrophenyl)carbamate

Similarity: 0.77

Nitroes

Chemical Structure| 4693-02-1

A262454 [4693-02-1]

6-Nitro-1H-benzo[d][1,3]oxazine-2,4-dione

Similarity: 0.82

Chemical Structure| 63480-10-4

A281431 [63480-10-4]

7-Nitro-1H-benzo[d][1,3]oxazine-2,4-dione

Similarity: 0.81

Chemical Structure| 7356-52-7

A118079 [7356-52-7]

3-Acetamido-4-methyl-2-nitrobenzoic acid

Similarity: 0.77

Chemical Structure| 1588441-20-6

A125012 [1588441-20-6]

tert-Butyl (2-methyl-3,5-dinitrophenyl)carbamate

Similarity: 0.77

Chemical Structure| 914348-97-3

A190567 [914348-97-3]

tert-Butyl 3-formyl-7-nitro-1H-indole-1-carboxylate

Similarity: 0.75