Structure of tert-Butyl Glycinate
CAS No.: 6456-74-2
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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: tert-Butyl 2-aminoacetate
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| CAS No. : | 6456-74-2 |
| Formula : | C6H13NO2 |
| M.W : | 131.17 |
| SMILES Code : | CC(C)(C)OC(=O)CN |
| Synonyms : |
tert-Butyl 2-aminoacetate
|
| MDL No. : | MFCD00038194 |
| InChI Key : | SJMDMGHPMLKLHQ-UHFFFAOYSA-N |
| Pubchem ID : | 151417 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H302-H315-H319-H332-H335 |
| Precautionary Statements: | P261-P280-P305+P351+P338 |
| Num. heavy atoms | 9 |
| Num. arom. heavy atoms | 0 |
| Fraction Csp3 | 0.83 |
| Num. rotatable bonds | 3 |
| Num. H-bond acceptors | 3.0 |
| Num. H-bond donors | 1.0 |
| Molar Refractivity | 34.99 |
| TPSA ? Topological Polar Surface Area: Calculated from |
52.32 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.68 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.19 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.29 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.39 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.01 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.51 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-0.57 |
| Solubility | 34.9 mg/ml ; 0.266 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-0.85 |
| Solubility | 18.7 mg/ml ; 0.142 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.79 |
| Solubility | 21.3 mg/ml ; 0.163 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 |
-6.97 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 |
1.0 |
| Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
| 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<1.0 |
| Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.03 |
* 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 |
|---|---|---|
| 79% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; | Coupling of fenofbric acid (1) with EDC / HOBT in Dichloromethane followed by t-butylglycine gave t-butyl protected 118 in 79% yield after chromatography (ethyl acetate/hexane) 1H-NMR (CDCl3): delta 7.74 (d, 2H, J= 9 Hz), 7.72 (d, 2H, J= 9 Hz), 7.53 (d, 2H, J= 8 Hz), 7.10 (d, 2H, J= 8 Hz), 3.83 (s, 2H), 1.60 (s, 6H), 1.45 (s, 9H) ppm. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With toluene-4-sulfonic acid; In toluene; at 130℃; for 4h; | To a solution of a compound 1 (262 mg, 2.0 mmol) in toluene (5 mL) were added a compound II (368 mg, 2.0 mmol) and p-toluenesulfonic acid monohydrate (19 mg, 0.1 mmol), and the resulting solution was stirred at 130 °C for 4 hours. The reaction mixture was poured into saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate, then the organic layer was washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, concentrated in vacuo to give a compound III (281 mg, Yield 47percent) as yellow oil. The obtained compound III was used for the next reaction without further purification. 1 H NMR (DMSO-d6) delta: 0.78-0.84 (m, 4H), 1.24-1.28 (m, 3H), 1.40 (s, 9H), 1.90-2.00 (m, 1H), 4.10-4.25 (m ,4.H), 5.78 (d, J = 1.2 Hz, 1H), 10.01 (brs, 1H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 64% | Isobutyl chloroformate (357.2 mg, 2.6 mmol) was dropwise added to a solution of <strong>[5683-31-8]3-(trimethylsilyl)propiolic acid</strong> 25 (372 mg, 2.6 mmol) and NMM (344 mg, 3.4 mmol) in THF (10 mL) at -40 oC. The reaction was stirred at -40 to -10 oC for 40 min. A solution of tert-butyl 2-aminoacetate 26 (447 mg, 3.4 mmol) and NMM (344 mg, 3.4 mmol) in co-solvents THF/DMF (5 mL/1 mL) was slowly added to the reaction solution at -40 oC for 20 min. The mixture slowly recovered to r.t. from -40oC and was stirred overnight at r.t.. After concentration, the residue was dissolved in CH2Cl2, washed by NaHCO3 and brine, dried by Na2SO4 and purified by silica gel column chromatography (5-10% EtOAc/Hexanes, stepwise gradient by 5%, then 10% iPrOH /Hexanes) to afford 27. Yield: 428 mg, 64%. 1H NMR (CDCl3, 600 MHz) 6.41 (b, 1H), 3.97 (d, J = 5.4 Hz, 1H), 1.49 (s, 9H), 0.23 (s, 9H). MS (ESI) [M+H]+ 256.4, found 256.0. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 85% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; | Amino acid S30 (27 mg, 0.065 mmol) and S31 (10 mg, 0.0599 mmol) were dissolved in 0.6 mL dry DMF, followed by addition of HATU (30mg, 0.077mmol), DIPEA (25|xL 0.1797 mmol). The resulting mixture was stirred under room temperature overnight and diluted with EtOAc. The solution was washed with 1M HCl and a saturated aqueous NaHCO3 solution. The combined organic phase was dried over Na2SO4 and concentrated, purified by silica gel column to afford compound S32 (27 mg, 85percent). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 48% | With 2,2':6',2'':6'',2'''-quaterpyridine; pentamethoxy tantalum; at 70℃; for 48h; | Amide compounds were produced by reacting an aminoester compound with an amino compound under the respective reaction conditions below in the presence of a Ta(OMe)5 catalyst and a ligand. The yield for each product is indicated below the formula. In the reaction formula below, L-ala represents an L-alanine residue, Val represents an L-valine residue, Leu represents an L-Leucine residue, ILe represents an L-isoleucine residue, Gly represents glycine residue, Phe represents an L-phenylalanine residue, and Thr(OtBu) represents O-(tert butyl) L-threonine residue. |