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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.
Cbz-Phe-OH is a phenylalanine derivative, widely used in polypeptide synthesis.
Synonyms: Z-Phe-OH
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Batch number can be found on the product's label following the word 'Batch'.
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 1161-13-3 |
Formula : | C17H17NO4 |
M.W : | 299.32 |
SMILES Code : | O=C(O)[C@@H](NC(OCC1=CC=CC=C1)=O)CC2=CC=CC=C2 |
Synonyms : |
Z-Phe-OH
|
MDL No. : | MFCD00020418 |
InChI Key : | RRONHWAVOYADJL-HNNXBMFYSA-N |
Pubchem ID : | 70878 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20℃; for 21h; | General procedure: A solution of N-Cbz amino acid 4 (1 mmol) and amino alcohol 5a (1 mmol) were dissolved in CH2Cl2(10 mL). To the solution, EDC (1.4 mmol) and HOBT (1 mmol) was added and the solution was stirred at 0 C for 1 h and room temperature for another 20 h. The reaction mixture was quenched with aqueous HCl (0.1 N) and extracted with AcOEt. The combined organic layer was washed with a saturated aqueous NaHCO3, brine, dried over anhydrous Na2SO4, and filterated. The filtrate was concentrated under reduced pressure to give the crude product which was used for the next step without further purification. To asolution of crude N-Cbz amino amide alcohols 6a-n in MeOH (10 mL) was added 5 % Pd/C (10 wt%)under hydrogen atmosphere and the mixture stirred at 50 C for 24 h. The reaction mixture was filtered and the solvent was evaporated under reduced pressure to give the residue. The residue was purified bycolumn chromatography on silica gel (AcOEt : hexane = 1 : 2) to afford the amino amide alcohol 7a-n.Compounds 7j-l were known compounds and were identified by spectral data which were in goodagreement with those reported. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | General procedure: N-protected amino acid was dissolved in dichloromethane (DCM). 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl, 1.3 eq.) and hydroxybenzotriazole (HOBt ·xH2O, 1.3 eq.) were added at 0 °C and the mixture was stirred for 50 min, after which thecorresponding amine (1.3 eq.) and N,N-Diisopropylethylamine (DIPEA, 1.3 eq.) were added at 0°C. After stirring overnight, the mixture was washed with a 5percent potassium sulfate solution(KHSO4), a 5percent sodium bicarbonate solution (NaHCO3) and with water. After drying over sodiumsulfate (Na2SO4) and evaporation of the solvent, the residue was purified via columnchromatography. |