Home Cart Sign in  
Chemical Structure| 20859-02-3 Chemical Structure| 20859-02-3

Structure of H-tert-Leu-OH
CAS No.: 20859-02-3

Chemical Structure| 20859-02-3

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

Synonyms: (S)-2-amino-3,3-dimethylbutanoic acid

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 [ 20859-02-3 ]

CAS No. :20859-02-3
Formula : C6H13NO2
M.W : 131.17
SMILES Code : CC(C)(C)[C@H](N)C(O)=O
Synonyms :
(S)-2-amino-3,3-dimethylbutanoic acid
MDL No. :MFCD00064218
InChI Key :NPDBDJFLKKQMCM-SCSAIBSYSA-N
Pubchem ID :164608

Safety of [ 20859-02-3 ]

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

Computational Chemistry of [ 20859-02-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 0
Fraction Csp3 0.83
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 35.18
TPSA ?

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

63.32 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.06
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

-1.77
Log Po/w (WLOGP)?

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

0.44
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.

-1.82
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

-0.31
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.48

Water Solubility

Log S (ESOL):?

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

0.59
Solubility 515.0 mg/ml ; 3.92 mol/l
Class?

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

Highly soluble
Log S (Ali)?

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

0.96
Solubility 1180.0 mg/ml ; 9.03 mol/l
Class?

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

Highly 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

-0.12
Solubility 100.0 mg/ml ; 0.762 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.

-8.36 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.

0.55

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

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)

1.28

Application In Synthesis of [ 20859-02-3 ]

* 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 [ 20859-02-3 ]

[ 20859-02-3 ] Synthesis Path-Downstream   1~17

  • 2
  • [ 652-12-0 ]
  • [ 20859-02-3 ]
  • (S)-3,3-dimethyl-2-(4,5,6,7-tetrafluoro-1,3-dioxoisoindolin-2-yl)butanoic acid [ No CAS ]
  • 6
  • [ 130723-13-6 ]
  • [ 20859-02-3 ]
  • (S)-2-(3-fluoro-5-(trifluoromethyl)phenylamino)-3,3-dimethylbutanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% (5)-2-(3-fluoro-5-(trifluoromethyl)phenyaniino)-3,3-dimethylbutanoic acid; (5)-2-amino-3,3-dimethylbutanoic acid (0.50 g, 3.81 mmol), K2CO3 (1.580 g, 11.44 mmol), copper(I) iodide (0.073 g, 0.38 mmol) and l-bromo-3-fiuoro-5- (trifluoromethyl)benzene (2.32 g, 9.53 mmol) in DMA (4 mL) was heated at 95 C for 32 hrs. H2O (15 mL) and ethyl ether (20 ml) was added. The aqueous phase was isolated and acidified with saturated KHSO4 solution, extracted with ether, dried over sodium sulfate. After removal of solvent, it gave (S)-2-(3-fluoro-5-(trifluoromethyl)phenylamino)-3,3- dimethylbutanoic acid (0.78 g, 70%) as white solid. LCMS (APCI-): 292.2. 1H NMR (400 MHz, d6-DMSO) delta 12.63 (s, 1H), 6.88 (s, 1H), 6.66 (d, 7=12.4 Hz, 1H), 6.61 (d, J-8.8 Hz, 1H), 6.40 (d, ,/=9.2 Hz, 1H), 3.71 (d, J=9.6 Hz, 1H), 0.98 (s, 9H).
  • 7
  • [ 130723-13-6 ]
  • [ 20859-02-3 ]
  • [ 75-65-0 ]
  • [ 1083092-63-0 ]
YieldReaction ConditionsOperation in experiment
6.90 g (77%) With lithium chloride; caesium carbonate;copper(I) iodide; General Procedure: (2S)-2-(3-Fluoro-5-trifluoromethyl-phenylamino)-3,3-dimethyl-butanoic acid (450) L-tert-leucine (4.0 g, 30.5 mmol, 1.0 eq.), lithium chloride (129 mg, 3.05 mmol, 0.1 eq.), copper(I) iodide (289 mg, 1.52 mmol, 0.05 eq.) and cesium carbonate (7.5 g, 22.9 mmol, 0.75 eq.) were charged into a 250 mL flask. tert-Butanol (100 mL) was added and the resulting mixture was stirred at 40 C. for 20 minutes, by which time the milky solution had turned blue. 3-Fluoro-5-trifluoromethyl-bromobenzene (7.41 g, 30.5 mmol, 1 eq.) was added dropwise, and the reaction mixture was heated at 100 C. for 15 hours. LCMS analysis of an aliquot showed around 20% (UV) of unreacted 3-Fluoro-5-trifluoromethyl-bromobenzene. Extra copper(I) iodide (289 mg, 0.05 eq.) was added and the reaction mixture was stirred at 100 C. for another 24 hours. LCMS analysis showed ~16% (UV) of remaining 3-Fluoro-5-trifluoromethyl-bromobenzene. Heating was stopped and the solvent removed under vacuum to give a blue solid. The solid was partitioned between ethyl acetate (100 mL) and water (100 mL). The pH of the aqueous phase was adjusted to pH=1 with 4M Hydrochloric acid (10 mL). The organic phase was collected, washed with 2M hydrochloric acid (2*100 mL) dried over sodium sulfate, filtered and the solvent removed under vacuum to give 6.90 g (77%) of the title compound as an orange solid which was used in the next step without further purification. 1H NMR (500 MHz, CHLOROFORM-d) delta ppm 6.61-6.75 (m, 2H) 6.49 (dt, J=10.68, 2.14 Hz, 1H) 4.48 (br. s., 1H) 3.79 (s, 1H) 1.11 (s, 9H) LC-MS: purity 100% (ELS) 90% (UV), tR 2.14 min m/z [M+H]+294.10
  • 8
  • [ 20859-02-3 ]
  • [ 148461-16-9 ]
  • 9
  • [ 139163-43-2 ]
  • [ 20859-02-3 ]
YieldReaction ConditionsOperation in experiment
With epichlorohydrin; In toluene; It was suspended in toluene (50 mL) and epichlorohydrin (5.8 g) was added. The reaction mixture was stirred till the pH was neutral. It was filtered, the solid obtained was stirred with acetone (15 ml*2) and again filtered to obtain L-tert-leucine (5.6 g, 75% yield, 98.5% chemical purity, 99.9% chiral purity).
With epichlorohydrin; In toluene; A mixture of L-tert-leucine.dibenzoyl-d-tartrate salt (27 g) as obtained in Example-1, water (150 mL) and concentrated hydrochloric acid (50 mL) was stirred for 12 hours. The liberated dibenzoyl-d-tartaric acid was filtered and dried (20 g). The filtrate was concentrated under reduced pressure to remove all the solvent. The residue obtained was stirred with acetone (15 ml x 2), filtered and dried to obtain colorless solid <strong>[139163-43-2]L-tert-leucine hydrochloride</strong> salt. It was suspended in toluene (50 mL) and epichlorohydrin (5.8 g) was added. The reaction mixture was stirred until the pH was neutral. It was filtered, the solid obtained was stirred with acetone (15 ml x 2) and again filtered to obtain L-tert-leucine (5.6 g, 75 % yield, 98.5 % chemical purity, 99.9% chiral purity).
  • 10
  • [ 20859-02-3 ]
  • [ 19547-38-7 ]
  • [ 117408-98-7 ]
  • 11
  • [ 20859-02-3 ]
  • [ 1206524-85-7 ]
  • 13
  • [ 20859-02-3 ]
  • 1-[4-(pyridin-2-yl)phenyl]-2,5-bis[N-(methoxycarbonyl)-L-tert-leucinyl]amino}-4(S)-hydroxy-6-phenyl-2-azahexane [ No CAS ]
  • [ 198904-31-3 ]
  • 14
  • [ 32703-79-0 ]
  • [ 20859-02-3 ]
  • (S)-N-(4-tert-butylphthalimido)-tert-leucine [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With triethylamine; In toluene; for 12h;Inert atmosphere; Reflux; [0056] To a mixture of 4-/er/-butylphthalic anhydride (0.514g, 2.52 mmol) and ter/-leucine (0.3g, 2.29 mmol) in anhydrous toluene, triethylamine (0.1 equiv) was added and the mixture was heated to reflux for 12 hours under nitrogen atmosphere. The reaction mixture was then diluted with ethyl acetate, washed with 0. I M HQ solution, dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was then purified on silica gel column chromatography using ethyl acetate-ft-hexane as an eluent to provide a colourless oil (0.7 g, 96%); [a]D25 = -0.35 ( 1 , CHCI3); R/= (1 : 1 ethyl acetate: ??-hexane); 1 H IM MR (400 MHz, CDCI3): delta; 7.88-7.71 (m, 3H, Ar-H), 4.69 (s, 1 H, NCH), 1 .34 (s, 9H, C(CHj)3), 1.15 (s, 9H, C(CHj)3); 1 C NMR (100 MHz, CDCI3): delta 173.3 (COOH ). 168.4, 168.0 (2 x CON), 158.9, 131 .8, 131 .3, 128.9, 123.4, 120.8 (6 x Ar-C), 59.8 (NCH), 35.7, 35.6 (2 x C(CH3)3), 31 .1 , 27.9 (2 x C(CH3)3); IR (film) v 2963, 2873, 171 1 , 1372, 1 101 , 908, 729 cm"1.
  • 15
  • [ 1721-26-2 ]
  • [ 20859-02-3 ]
  • [ 31931-53-0 ]
  • [ 545394-60-3 ]
  • 16
  • [ 20859-02-3 ]
  • C12H14N2O2 [ No CAS ]
  • [ 75-64-9 ]
  • [ 1425038-21-6 ]
  • 17
  • [ 130723-13-6 ]
  • [ 20859-02-3 ]
  • [ 1083092-67-4 ]
 

Historical Records

Technical Information

Categories