Structure of Boc-Tyr-OH
CAS No.: 3978-80-1
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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.
Synonyms: (S)-2-((tert-Butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoic acid
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 3978-80-1 |
Formula : | C14H19NO5 |
M.W : | 281.30 |
SMILES Code : | OC(C=C1)=CC=C1C[C@@H](C(O)=O)NC(OC(C)(C)C)=O |
Synonyms : |
(S)-2-((tert-Butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoic acid
|
MDL No. : | MFCD00037179 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 20 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.43 |
Num. rotatable bonds | 7 |
Num. H-bond acceptors | 5.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 73.37 |
TPSA ? Topological Polar Surface Area: Calculated from |
95.86 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.97 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.71 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.91 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.42 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.18 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.84 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.05 |
Solubility | 0.25 mg/ml ; 0.000888 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.38 |
Solubility | 0.0118 mg/ml ; 0.000042 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.6 |
Solubility | 0.71 mg/ml ; 0.00252 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 |
-6.09 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 |
0.0 |
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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.68 |
* 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 |
---|---|---|
0.4 g | With lithium aluminium tetrahydride; In diethyl ether;Inert atmosphere; Reflux; | N-Boc-L-tyrosinol 4: 1?g of N-Boc-L-tyrosine (3.6?mmol) was dissolved under nitrogen in 80?mL of dry diethyl ether. Then lithium aluminium hydride (0.4?g, 0.01?mol) was added in portions. The suspension was heated to reflux overnight. After cooling to room temperature, ethyl acetate was added and the reaction mixture was poured carefully to concentrated sodium hydroxide solution while stirring. The organic layer was extracted with water and dried with sodium sulphate. 0.4?g oily material was obtained after removing the solvents. 1H NMR (400?MHz, CDCl3): delta 1.37 (9H, s), 2.69 (2H, d, J?=?6.51?Hz), 3.47 (1H, dd, J?=?5.27, 10.85?Hz), 3.57 (1H, dd, J?=?3.75, 10.85?Hz), 3.76 (1H, s), 5.06 (1H, d, J?=?7.75?Hz), 6.70 (2H, d, J?=?8.37?Hz), 6.97 (2H, d, J?=?8.37?Hz), 7.70 (1H, br s) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With triethylamine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; acetonitrile; at 0℃; for 7h; | A solution of LDOPAmethyl ester hydrochloride 2 (0.27 g, 1.11 mmol) andN-(tert-butoxycarbonyl)-L-tyrosine (0.33 g, 1.16 mmol) inDMF (2.2 mL) and acetonitrile (9 mL) was cooled in ice.With stirring, triethylamine (0.16 mL, 1.11 mmol) was addedfollowed by dicyclohexylcarbodiimide (0.25 g, 1.11 mmol).After 7 h of continued stirring at 0 C, the reaction mixturewas cooled in the freezer overnight. The insoluble materialwas filtered off and washed with ethyl acetate. The combinedfiltrate was evaporated and the residue was dissolvedin ethyl acetate (40 mL) and water (25 mL). The organiclayer was washed successively with 25 mL portions of 0.5 NHCl, H2O, 0.5 N NaHCO3 and brine and dried over MgSO4.After filtration and concentration, the crude yellow solid wassubjected to silica chromatography (ethyl acetate/hexane =1:1, then 3:1) to afford a colorless amorphous mass (0.34 g,64%) 1H NMR (CD3OD): 1.34 (s, 3H), 2.67 (m, 1H), 2.90(m, 3H), 3.35 (s, 3H), 3.66 (s, 3H), 4.23 (t, J = 6.9 Hz, 1H),4.59 (t, J = 6.8 Hz, 1H), 6.48 (d, J = 7.9 Hz, 1H), 6.62 (s,1H), 6.68 (d, J = 7.9 Hz, 1H), 6.69 (d, J = 8.6 Hz, 2H), 7.01(d, J = 8.6 Hz, 2H); 13C NMR (CD3OD): 28.6, 37.9, 38.4,52.6, 55.2, 57.5, 80.7, 116.1. 116.3, 117.2, 121.7, 129.0,129.1, 131.3, 145.3, 146.2, 157.1, 157.5, 173.2, 174.2;HRMS (ESI): calcd. for C24H31N2O8 (M++H) 475.2080,found 475.2055; []D -2.1 (c 2.0, CH3OH). |