Structure of Cbz-Pro-OMe
CAS No.: 5211-23-4
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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: Methyl(S)-N-(benzyloxycarbonyl)prolinate; N-Z-L-proline methyl ester
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| CAS No. : | 5211-23-4 |
| Formula : | C14H17NO4 |
| M.W : | 263.29 |
| SMILES Code : | O=C(N1[C@H](C(OC)=O)CCC1)OCC2=CC=CC=C2 |
| Synonyms : |
Methyl(S)-N-(benzyloxycarbonyl)prolinate; N-Z-L-proline methyl ester
|
| English Name : | (S)-1-Benzyl 2-methyl pyrrolidine-1,2-dicarboxylate |
| MDL No. : | MFCD00134246 |
| InChI Key : | BLQYEDXWEDWCNJ-LBPRGKRZSA-N |
| Pubchem ID : | 688168 |
| Num. heavy atoms | 19 |
| Num. arom. heavy atoms | 6 |
| Fraction Csp3 | 0.43 |
| Num. rotatable bonds | 6 |
| Num. H-bond acceptors | 4.0 |
| Num. H-bond donors | 0.0 |
| Molar Refractivity | 72.71 |
| TPSA ? Topological Polar Surface Area: Calculated from |
55.84 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.85 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.74 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.43 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.57 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.55 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.83 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-2.41 |
| Solubility | 1.03 mg/ml ; 0.00392 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-2.53 |
| Solubility | 0.778 mg/ml ; 0.00296 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.79 |
| Solubility | 0.432 mg/ml ; 0.00164 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) |
Yes |
| 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 |
-6.67 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 |
0.55 |
| PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
| Brenk? Structural Alert: implemented from |
1.0 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) |
2.84 |
* 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 |
|---|---|---|
| 83% | With lithium aluminium tetrahydride |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: 1.) 2.0 M (CH3)3Al / 1.) benzene, toluene, 0 deg C, 5 min., r.t., 1.5 h, 2.) benzene, reflux, 4 h 2: 99 percent / H2 / 5 percent Pd/C / methanol / Ambient temperature |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: 3.95 g / tetrahydrofuran / 4 h 2: lithium aluminum hydride / tetrahydrofuran / 2 h / Heating |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 5 steps 1: 89 percent / tetrahydrofuran; diethyl ether / 1.) -20 deg C, 0.5 h, 2.) 0 deg C, 1 h 2: 86 percent / H2 / 5percent Pd/C / methanol / 3 h / Ambient temperature 3: 90 percent / CH2Cl2 / 48 h / Ambient temperature 4: 1.) sodium hydride, DMSO, triphenylmethane / 1.) RT, 2.) 10 min 5: 86 percent / 10percent KOH / 1.5 h / Heating |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 94% | NaClO2 (498 mg, 5.507 mmol) was added to a mixed solution containing 150 mg (1.101 mmol) of 3-phenylpropanol in a CH2Cl2 (3.7 mL)-NaH2PO4 aqueous solution (2.1 mL, 0.52 M solution being 1.0 equivalent), followed by stirring. Then, Me-AZADO+Cl- (11.1 mg, 0.05507 mmol) was immediately added, followed by vigorous stirring at room temperature until disappearance of the starting material 3-phenylpropanol and its aldehyde product 3-phenylpropanal was confirmed. After completion of the reaction, 2-methyl-2-butene (1.17 mL, 11.01 mmol) was added under cooling with ice, and an aqueous layer and an organic layer were separated under a weakly acidic condition. To the organic layer, a 10percent sodium hydroxide aqueous solution was added to obtain a solution having a pH 11, from which organic substances other than the ionic carboxylic acid were extracted with diethyl ether. The remained aqueous layer was adjusted to pH 3 with 10percent hydrochloric acid, and from the aqueous layer, a molecular type carboxylic acid was extracted with diethyl ether. The organic layer was washed with an aqueous sodium chloride solution and then dried over magnesium sulfate, and the solvent was distilled off under reduced pressure.The residue was dissolved in methylene chloride, and diazomethane was added under cooling with ice, and after confirming the completion of a methyl esterification reaction, stirring was continued at room temperature for a while. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 176 mg (yield: 97percent) of a methyl ester.Cases wherein the reaction was carried out in the same manner, are shown with respect to the case where Me-AZADO+Cl- was employed and the case where TEMPO+CL- was employed. Here, in the Table, "alcohol" represents the alcohol, "time (hr)" represents the reaction time (unit: hr), "yield (percent)" represents the yield (percent) which was calculated by the isolated yield of the methyl ester by the diazomethane. "note" represents a note, "trace" represents a trace amount, "Additive" represents an additive, "SASS" represents sodium stearate, and "slight chlorination" means that slight chlorination was observed. "Cat." represents the catalyst. TABLE 1 yield percent No. alcohol time [hr] note 1 1.5 77 97 2 1.5 63 93 3 10 trace 84 4 32 trace 86 5 5.5/6.5 trace 99/96Additive (5 mol percent) PhCO2II/ SASS* 6 4.5 20 91 7 10 25 90 8 24 <16 <84 slight chlorination 9 3 <13 <92 slight chlorination cat. 20 mol percent 10 5 - 92 11 1 - 88 12 15 trace 94 SASS*: Stearic Acid Sodium Salt |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 62% | With O-(diphenylphosphinyl)hydroxylamine; potassium carbonate at 20℃; for 12h; Inert atmosphere; Irradiation; Sealed tube; |

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