 
                                
                                 
                                
                                
                                    Structure of Boc-D-Leu-OH
                                    
                                    
CAS No.: 16937-99-8
                                    
                                
 
                                 
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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-Butoxycarbonyl)-D-leucine
 
                
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| CAS No. : | 16937-99-8 | 
| Formula : | C11H21NO4 | 
| M.W : | 231.29 | 
| SMILES Code : | CC(C)C[C@@H](NC(OC(C)(C)C)=O)C(O)=O | 
| Synonyms : | 
                                (tert-Butoxycarbonyl)-D-leucine
                             | 
| MDL No. : | MFCD00038294 | 
| GHS Pictogram: |   | 
| Signal Word: | Warning | 
| Hazard Statements: | H302-H315-H319-H335 | 
| Precautionary Statements: | P261-P305+P351+P338 | 
| Num. heavy atoms | 16 | 
| Num. arom. heavy atoms | 0 | 
| Fraction Csp3 | 0.82 | 
| Num. rotatable bonds | 7 | 
| Num. H-bond acceptors | 4.0 | 
| Num. H-bond donors | 2.0 | 
| Molar Refractivity | 61.28 | 
| TPSA ? Topological Polar Surface Area: Calculated from  | 75.63 Ų | 
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from  | 2.34 | 
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by  | 2.25 | 
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from  | 2.01 | 
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from  | 1.42 | 
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by  | 0.9 | 
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 1.79 | 
| Log S (ESOL):? ESOL: Topological method implemented from  | -2.23 | 
| Solubility | 1.36 mg/ml ; 0.0059 mol/l | 
| Class? Solubility class: Log S scale  | Soluble | 
| Log S (Ali)? Ali: Topological method implemented from  | -3.47 | 
| Solubility | 0.0776 mg/ml ; 0.000336 mol/l | 
| Class? Solubility class: Log S scale  | Soluble | 
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by  | -1.49 | 
| Solubility | 7.5 mg/ml ; 0.0324 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 | Yes | 
| 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  | -6.11 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<1.0 | 
| Synthetic accessibility? Synthetic accessibility score:  from 1 (very easy) to 10 (very difficult) | 2.79 | 
* 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 | 
|---|---|---|
| 100% | With 2,3,4-lutidine; 1-hydroxy-7-aza-benzotriazole; diisopropyl-carbodiimide; In N,N-dimethyl-formamide; at 20℃; for 3h;Product distribution / selectivity; | A solution of Boc-D-Leu-OH (150 mg, 0.649 rnmol), 9-fluorenylmethyl carbazate (164.9 mg, 0.649 mmol), HOAt (88.3 mg, 0.649 mmol), and collidine (428.5 muL, 3.243 mmol) in DMF (1 mL) was treated with DIC (200.8 muL, 1.297 mmol), and stirred at room temperature under nitrogen for 3 hours. The reaction mixture was diluted with ethyl acetate (25 mL), washed consecutively with 10percent citric acid (3 x 25 mL), 10percent NaHCO3 (3 x 25 mL), water (25 mL), and saturated NaCl (25 mL), dried ( MgSO4), filtered, and concentrated under reduced pressure to give the title compound as a colorless solid. (302 mg, 100percent). 1H NMR (CDCl3): delta 8.21 (s, IH), 7.74 (d, J= 7.8 Hz, 2H), 7.57 (d, J= 7.8 Hz, 2H), 7.38 (t, J= 7.5 Hz, 2H), 7.29 (t, J= 7.5 Hz, 2H), 6.79 (s, IH), 4.85 (s, IH), 4.43 (d, J= 7.2 Hz, 2H), 4.18 (s, IH), 3.96 (s, IH), 1.72 (m, 2H), 1.43 (s, 9H), 1.25 (m, IH), 0.94 (d, J= 6.6 Hz, 3H), 0.92 (d, J= 6.6 Hz, 3H). MS: m/e 368.3 [M+H-Boc] (35percent), 490.2 [M+Na] (100percent). | 
| 100% | A solution of Boc-D-Leu-OH (134 mg, 0.536 mmol), HOAt (73 mg, 0.54 mmol) and TMP (0.87 mL, 2.7 mmol) in anhydrous DMF (2 mL) was treated with DIC (135 mg, 1.07 mmol), and stirred at ambient temperatures under nitrogen for 20 minutes. The solution was treated with 9-fluorenylmethyl carbazate (136 mg, 0.536 mmol) and stirred for 5 hours. The solution was diluted with dichloromethane (20 mL), washed consecutively with 10percent citric acid (3 X 20 mL), saturated NaHCO3 (20 mL), and saturated NaCl (20 mL), dried (MgSO4), filtered, and concentrated to give crude title compound as a viscous oil (271 mg, 108percent). MS (ESI): 368.3 (95, M+H), 490.2 (100, M+Na). | 
 [ 16937-99-8 ]
                                                    
                                                    [ 16937-99-8 ]

 [ 71989-38-3 ]
                                                    
                                                    [ 71989-38-3 ]
 [ 132388-59-1 ]
                                                    
                                                    [ 132388-59-1 ]
 [ 1072-84-0 ]
                                                    
                                                    [ 1072-84-0 ]



 [ 16937-99-8 ]
                                                    
                                                    [ 16937-99-8 ]

 [ 71989-38-3 ]
                                                    
                                                    [ 71989-38-3 ]
 [ 132388-59-1 ]
                                                    
                                                    [ 132388-59-1 ]
 [ 1072-84-0 ]
                                                    
                                                    [ 1072-84-0 ]



 [ 16937-99-8 ]
                                                    
                                                    [ 16937-99-8 ]

 [ 71989-38-3 ]
                                                    
                                                    [ 71989-38-3 ]
 [ 132388-59-1 ]
                                                    
                                                    [ 132388-59-1 ]
 [ 1072-84-0 ]
                                                    
                                                    [ 1072-84-0 ]


