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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.
Ac-Phe-OEt is a phenylalanine derivative, used for peptide synthesis and drug chemistry research.
Synonyms: (S)-Ethyl 2-acetamido-3-phenylpropanoate
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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'.
Search for reports by entering the product batch number.
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CAS No. : | 2361-96-8 |
Formula : | C13H17NO3 |
M.W : | 235.28 |
SMILES Code : | O=C(OCC)[C@@H](NC(C)=O)CC1=CC=CC=C1 |
Synonyms : |
(S)-Ethyl 2-acetamido-3-phenylpropanoate
|
MDL No. : | MFCD00026885 |
InChI Key : | YIVZYFDBEPMPNL-LBPRGKRZSA-N |
Pubchem ID : | 94229 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-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 protease from Bacillus licheniformis type VIII; In hexane; at 25℃; for 5h;pH 7.8;Enzymatic reaction; | General procedure: The transesterification reaction was carried out as described earlier.45 The reaction mixture contained 20 mM <strong>[2361-96-8]N-acetyl-L-phenylalanine ethyl ester</strong> and 1M n-propanol/n-butanol in anhydrous n-hexane. The enzyme preparation as prepared above was added to the reaction mixture and shaken at 200 rpm at 25 C. The product was assayed by high performance liquid chromatography (HPLC) using a Zorbax C-18 reversed phase column (150 mm ×4.6 mm × 5μ) at a flow rate of 1mL/min (eluent used was water:acetonitrile:glacial acetic acid=55:40:5 v/v) at 258 nm, and the initial rate was obtained from the linear portion of the reaction trajectory.45 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
> 99% | With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; C47H43FeNOP2; In 1,2-dichloro-ethane; at 20℃; under 7500.75 Torr; for 12h;Inert atmosphere; Sealed tube; | A magnetic stirrer bar in a vial was added Rh(cod)2BF4 (0.8 mg, 0.002 mmol), (Rc,Rp)-L4 (1.6 mg, 0.022 mmol) and shifted to a glove-box under nitrogen atmosphere. The reaction mixture was dissolved in 1,2-dichloroethane (1 mL) and stirred for 1 hour. After then, the substrates (0.2 mmol) in DCE (1 mL) was added to above catalyst solution and vials were transferred to the stainless steel autoclave under nitrogen atmosphere in a glove-box, and then sealed. The autoclave was now removed from glove-box and purged three times with H2 gas, and then set H2 pressure at 10 bar. After 12 h stirring at room temperature, the H2 pressure was released in a fuming hood. The solvent was removed under the reduced pressure and the residue was subjected to column chromatography to purify the product. Analysis of 1H NMR confirmed the formation of product. Conversions were determined by GC analysis of an aliquot crude mixture. The enantiomeric excess (ee) of the product was ascertained via chiral HPLC. (S)-Ethyl 2-acetamido-3-phenylpropanoate (8a) Obtained in >99 % yield as white powder after hydrogenation of substrate 7a. [α]D20 = -50.5 (c = 1.0, CHCl3). 96 % ee was determined by HPLC analysis employing a chiralpak AD-H column, n-hexane/i-PrOH = 95:5, 1.0 mL/min, 254 nm; tR = 13.375 (major), tR = 20.128 (minor). 1H NMR (400 MHz, CDCl3) δ 7.30-7.24 (m, 3H), 7.20 - 7.01 (m, 2H), 6.02 (s, 1H), 4.86 (m, 1H), 4.22 - 4.08 (m, 2H), 3.20 - 3.02 (m, 2H), 1.98 (s, 3H), 1.24 (t, J = 7.1 Hz, 3H). The absolute configuration was determined by comparing the retention time with literature data.[1] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With quinine; In tetrahydrofuran; at 30℃; for 72h;Catalytic behavior; | General procedure: A solution of hemimalonic ester 2c (25 mg, 0.09 mmol, 1 eq) and QD-thiourea 4a (53.2 mg, 0.09 mmol, 1 eq) in 2 mL of dry THF was stirred at 30 C. The reaction was monitored by TLC (cyclohexane/ethyl acetate: 6/4). After completion of the reaction, the solvent was removed under reduced pressure and the crude product was purified by flash chromatography (cyclohexane/ethyl acetate: 6/4 then 1/1). The ee was determined by chiral HPLC [Daicel Chiralpak IA, n-heptane: isopropanol =80:20, 1.0 mL/min, λ = 204 nm. Racemic standard is Tr1 = 5.2 min, Tr2 = 6.7 min]. | |
With C44H48N6O4; In tetrahydrofuran; at 30℃; for 72h;Catalytic behavior; | General procedure: A solution of hemimalonic ester 2c (25 mg, 0.09 mmol, 1 eq) and QD-thiourea 4a (53.2 mg, 0.09 mmol, 1 eq) in 2 mL of dry THF was stirred at 30 C. The reaction was monitored by TLC (cyclohexane/ethyl acetate: 6/4). After completion of the reaction, the solvent was removed under reduced pressure and the crude product was purified by flash chromatography (cyclohexane/ethyl acetate: 6/4 then 1/1). The ee was determined by chiral HPLC [Daicel Chiralpak IA, n-heptane: isopropanol =80:20, 1.0 mL/min, λ = 204 nm. Racemic standard is Tr1 = 5.2 min, Tr2 = 6.7 min]. |