Home Cart Sign in  
Chemical Structure| 94994-39-5 Chemical Structure| 94994-39-5

Structure of 94994-39-5

Chemical Structure| 94994-39-5

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

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

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

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 [ 94994-39-5 ]

CAS No. :94994-39-5
Formula : C10H19NO4
M.W : 217.26
SMILES Code : O=C(O)CCCN(C(OC(C)(C)C)=O)C
MDL No. :MFCD09831984
InChI Key :PXAKQDWAISFHCM-UHFFFAOYSA-N
Pubchem ID :10656390

Safety of [ 94994-39-5 ]

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

Computational Chemistry of [ 94994-39-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 0
Fraction Csp3 0.8
Num. rotatable bonds 7
Num. H-bond acceptors 4.0
Num. H-bond donors 1.0
Molar Refractivity 56.56
TPSA ?

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

66.84 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.03
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

0.97
Log Po/w (WLOGP)?

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

1.72
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.

1.13
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

1.25

Water Solubility

Log S (ESOL):?

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

-1.34
Solubility 10.0 mg/ml ; 0.0461 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.

-1.96
Solubility 2.37 mg/ml ; 0.0109 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

-1.1
Solubility 17.3 mg/ml ; 0.0796 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

Yes
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.

-6.94 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.

0.56

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)

2.13

Application In Synthesis of [ 94994-39-5 ]

* 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.

  • Downstream synthetic route of [ 94994-39-5 ]

[ 94994-39-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 24424-99-5 ]
  • [ 6976-17-6 ]
  • [ 94994-39-5 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine; In dichloromethane; at 20℃; for 72h; Example 12; Preparation of 4-(ter*-Butoxycarbonylmethylamino)butyric Acid To a stirred mixture of <strong>[6976-17-6]4-(methylamino)butyric acid hydrochloride</strong> (1.00 g, 6.51 mmol) and triethylamine (2.72 mL, 19.5 mmol) in DCM (60 mL) at room temperature was added di-tert-butyldicarbonate (1.56 g, 7.16 mmol). The resulting mixture was stirred for about 72 h. LC-MS showed product was present (Rt 4.11 min; m/z 216.2 [M + H]+). DCM and water were added and the pH of the aqueous layer was adjusted to pH 4.5 to 6 with aqueous hydrochloric acid (1 M). The layers were separated and the organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (1.5 g, 100 percent yield) as light yellow thick oil.1H NMR (CDCl3) delta 3.28 (br s); 2.85 (s); 2.35 (t); 1.84 (t); 1.46 (s).
96% With triethylamine; In methanol; at 20℃; for 1.16667h; Di-t-butyl dicarbonate (7 g, 32.1 mmol) was added dropwise over 10 minutes to a mixture of <strong>[6976-17-6]4-(methylamino)butyric acid hydrochloride</strong> (5 g, 32.5 mmole) in MeOH (50 mL) and 3 eq. Et3N (5 mL). The reaction mixture was stirred at room temperature for 1 hour and then concentrated under reduced pressure. The residue was dissolved in EtOAc (150 mL), and washed with an ice-cold 0.1 N aqueous HCl solution (2.x.70 mL). The organic layer was then washed with water (2.x.100 mL) to neutral pH, and then washed with sat. NaCl (1.x.100 mL). The EtOAc layer was dried over Na2SO4 and concentrated to give the Boc-protected product (6.8 g, 96percent yield).
70% [0335] To a stirred solution of <strong>[6976-17-6]4-(methylamino)-butyric acid hydrochloride</strong> (303 mg, 1.97 mmol) and dioxane (2 mL) in saturated aqueous NaHCO3 (2 mL) was added added di-tert-butyl di-carbonate (523 mg, 2.40 mmol) and the mixture was stirred at 0° C. for 20 minutes followed by stirring at room temperature for 22 hours. The reaction was concentrated under reduced pressure and the residue was diluted with water (20 mL). The aqueous phase was extracted with ethyl acetate (2.x.15 mL). The aqueous phase was treated with 5percent w/v aqueous citric acid until a pH of 4 was obtained. The aqueous phase was then again extracted with ethyl acetate (4.x.15 mL). The combined organic phase was dried (MgSO4), filtered and concentrated under reduced pressure to give a colourless oil (300 mg, 70percent). [0336] To a stirred solution of the N-protected acid from above (143 mg, 0.659 mmol) in THF (5 mL) was added BH3.THF (1.0M in THF, 2.5 mmol) and the mixture was stirred at 50° C. for 64 hours. Dry CH3OH (5 mL) was added, and the mixture stirred at 70° C. for 1 hour. The reaction was concentrated under reduced pressure. The crude yellow oil (148 mg) was purified by column chromatography (2 cm OD, 20 g silica, 1:1 EtOAc: hexanes) to afford the N-protected alcohol (71 mg, 53percent). [0337] To a suspension of the N-protected alcohol from above (71 mg, 0.35 mmol), NMO (65 mg, 0.56 mmol) and 3 molecular sieves (186 mg) in CH2Cl2 (2.55 mL) was added TPAP (13 mg, 0.04 mmol) and the mixture was stirred at room temperature for 1 hour. The mixture was filtered through a silica gel plug with ethyl acetate. The filtrate was concentrated under reduced pressure to give a yellow oil (46 mg, 65percent). [0338] Using the General Procedure B: To a stirred solution of the N-protected aldehyde from above (46 mg, 0.229 mmol) and [1-(tert-butyloxycarbonyl)-(1H-benzimidazol-2-ylmethyl)]-(5,6,7,8-tetrahydroquinolin-8-yl)-amine (89 mg, 0.229 mmol) in CH2Cl2 (2.55 mL) was added NaBH(OAc)3 (100 mg, 0.47 mmol) and the mixture was stirred for 19 hours. Purification of the crude yellow oil (126 mg) by flash chromatography (12 g silica, 50:1:1 CH2Cl2: CH3OH: NH4OH) afforded the N-protected tertiary amine (80 mg, 62percent). [0339] Using the General Procedure D: The N-protected tertiary amine from above (76 mg, 0.135 mmol) was converted to COMPOUND 34 as a white solid (71 mg, 75percent). 1H NMR (D2O) delta 1.54 (br s, 4H), 1.74-1.90 (m, 1H), 1.95-2.09 (m, 1H), 2.13-2.23 (m, 1H), 2.32-2.42 (m, 1H), 2.50-2.64 (m, 4H) containing 2.61 (s, 3H), 2.77-2.94 (m, 3H), 2.97-3.04 (m, 2H), 4.39 (d, 1H, J=17.1 Hz), 4.47-4.60 (m, 2H) containing 4.53 (d, 1H, J=17.2 Hz), 7.60 (dd, 2H, J=6.1, 3.0 Hz), 7.80 (dd, 2H, J=6.1, 3.0 Hz), 7.86 (dd, 1H, J=7.9, 6.2 Hz), 8.34 (d, 1H, J=7.9 Hz), 8.62 (d, 1H, J=5.0 Hz). 13C NMR (D2O) delta 20.42 (2 carbons), 23.69, 25.40, 27.64, 33.05, 48.23, 49.00, 51.68, 60.66, 114.25 (2 carbons), 125.93, 126.93 (2 carbons), 130.97, 139.31, 140.61, 148.10, 151.25, 151.77. ES-MS m/z 364 (M+H). Anal Calc. for C21H25N5O.3.2HBr.1.9H2O: C, 38.41; H, 4.91; N, 10.67; Br, 38.94. Found: C, 38.53; H, 5.02; N, 10.42; Br, 38.79.
a) 4-(N-tert-Butoxycarbonyl-N-methylamino)butyric acid Using <strong>[6976-17-6]4-(N-methylamino)butyric acid hydrochloride</strong> (23 g, 150 mmol) and di-tert-butyl dicarbonate (32.7 g, 150 mmol), the title compound was obtained as an oil according to the method of Example 1(a) (31 g, yield: 95percent).
With triethylamine; In tetrahydrofuran; at 25℃; A solution of <strong>[6976-17-6]4-(methylamino)butyric acid hydrochloride</strong> (2.0 g, 13.0 mmol) in 25 mL of THF at 25° C. was treated with Boc2O (4.3 g, 19.5 mmol) and Et3N (7.3 mL, 52.0 mmol), and the mixture was stirred overnight before being quenched with the addition of 40 mL of aqueous 1N NaOH. The mixture was washed with CH2Cl2 (2.x.100 mL), cooled to 0° C., acidified (pH 5-6) with the addition of aqueous 3.5 N HCl, and extracted with CH2Cl2 (2.x.75 mL). The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure to give 4-[[(1,1-dimethylethyl)oxy]carbonyl}(methyl)amino]butanoic acid as a white solid.
With potassium carbonate; In 1,4-dioxane; water; for 6h; 3 g of <strong>[6976-17-6]4-(methylamino)butyric acid hydrochloride</strong>, 7 g of potassium carbonate in 40 mL of 1,4-dioxane and 20 mL of water are placed in a round-bottomed flask. Next, 4.86 g of di-tert-butyl dicarbonate are added. After stirring for 6 hours, the dioxane is evaporated off and 30 mL of water are then added. Aqueous 1 M potassium bisulfate solution is added until pH 2 is obtained. The resulting mixture is extracted twice with 10 mL of ethyl acetate, dried over sodium sulfate, filtered and concentrated to dryness under reduced pressure. 4.37 g of 4-(tert-butoxycarbonylmethylamino)butyric acid are obtained.

  • 2
  • [ 6976-17-6 ]
  • [ 94994-39-5 ]
YieldReaction ConditionsOperation in experiment
a) 4-(N-tert-Butyloxycarbonyl-N-methylamino)butyric acid Using <strong>[6976-17-6]4-methylaminobutyric acid hydrochloride</strong> (30 g, 200 mmol), a reaction was performed in the same manner as described in Example 1 (a) to obtain the title compound as an oil (44.08 g, quantitative). 1H-NMR (CDCl3): 3.28 (t, 2H), 2.85 (s, 3H) 2.36 (t, 2H), 1.85 (m, 2H), 1.45 (s, 9H)
 

Historical Records

Technical Information

Categories