Structure of H-D-Leu-OBzl·HCl
CAS No.: 68838-94-8
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CAS No. : | 68838-94-8 |
Formula : | C13H20ClNO2 |
M.W : | 257.76 |
SMILES Code : | CC(C)C[C@@H](N)C(OCC1=CC=CC=C1)=O.[H]Cl |
MDL No. : | MFCD20264816 |
InChI Key : | HCYLOEGSAOVRIT-UTONKHPSSA-N |
Pubchem ID : | 22821561 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-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 |
---|---|---|
100% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 5.33333h;Inert atmosphere; | a) Preparation of N-(p-methoxylphenylacetyl)-D-leucine benzyl ester[0196] P- methoxyl phenylacetic acid (1.29g) , D- leucine benzyl ester hydrochloride (2g) and DIEA (2.2g) were dissolvedin anhydrous dichloromethane (60ml) , cooled down to 0C under the protection of nitrogen, and then HOBt (1.1g)and EDCI (1.8g) were added. The resulting mixture was stirred at 0C for 20min and allowed to warm up naturally toroom temperature to react for 5 hours. The organic layer was washed in turn with 5% potassium hydrosulphate solution,saturated sodium hydrogencarbonate solution and saturated saline solution, dried over anhydrous sodium sulfate, filteredand concentrated under reduced pressue to give 4.1g crude product, which was purified with column chromatographyto give a colourless oil (3.06g, yield: 100%) . The content was 99% (HPLC, mobile phase 1, method 1) .Rf = 0.2Developer: petroleum ether: ethyl acetate = 4: 1Color development: ultraviolet, iodine and 1% ninhydrin solutionMS: 370 (M+H) |
With benzotriazol-1-ol; | a) Preparation of N-(p-methoxylphenylacetyl)-D-leucine benzyl ester P-methoxyl phenylacetic acid (1.29 g), <strong>[68838-94-8]D-leucine benzyl ester hydrochloride</strong> (2 g) and DIEA (2.2 g) were dissolved in anhydrous dichloromethane (60 ml), cooled down to 0 C. under the protection of nitrogen, and then HOBt (1.1 g) and EDCI (1.8 g) were added. The resulting mixture was stirred at 0 C. for 20 min and allowed to warm up naturally to room temperature to react for 5 hours. The organic layer was washed in turn with 5% potassium hydrosulphate solution, saturated sodium hydrogencarbonate solution and saturated saline solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 4.1 g crude product, which was purified with column chromatography to give a colourless oil (3.06 g, yield: 100%). The content was 99% (HPLC, mobile phase 1, method 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.14 g | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 40℃; for 36h; | a) Preparation of N-(t-butyloxycarbonyl)methyl-D-leucine benzyl ester[0134] D- leucine benzyl ester hydrochloride (3.9g) was dissolved in DMF (30ml) , DIEA (3.9g) was added, tert- butylbromoacetate (3.2g) was added dropwisely slowly, and the resulting mixture was allowed to react at 40C for 36h, andconcentrated under reduced pressue to remove a great quantity of solvent, ethyl acetate (50ml) was added, and theorganic phase was washed with saturated sodium hydrogencarbonate solution (50ml33) , 5% KHSO4 solution (50ml33)and water until to be neutral, and washed with saturated saline solution (50ml31) , dried over anhydrous sodium sulfate, and the filtrate was concentrated to give 5.2g yellow oil, which was purified on a column to give 4.14g light yellow- greenoil. The content was 96% (HPLC, mobile phase 1, method 1) .Rf = 0.5Developer: petroleum ether: ethyl acetate = 2: 1Color development: ultraviolet, iodine and 1% ninhydrin solutionMS: 358 (M+Na) |
In ethyl acetate; N,N-dimethyl-formamide; | a) Preparation of N-(t-butyloxycarbonyl)methyl-D-leucine benzyl ester <strong>[68838-94-8]D-leucine benzyl ester hydrochloride</strong> (3.9 g) was dissolved in DMF (30 ml), DIEA (3.9 g) was added, tert-butyl bromoacetate (3.2 g) was added dropwisely slowly, and the resulting mixture was allowed to react at 40 C. for 36 h, and concentrated under reduced pressure to remove a great quantity of solvent, ethyl acetate (50 ml) was added, and the organic phase was washed with saturated sodium hydrogencarbonate solution (50 ml*3), 5% KHSO4 solution (50 ml*3) and water until to be neutral, and washed with saturated saline solution (50 ml*1), dried over anhydrous sodium sulfate, and the filtrate was concentrated to give 5.2 g yellow oil, which was purified on a column to give 4.14 g light yellow-green oil. The content was 96% (HPLC, mobile phase 1, method 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.1 g | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 60℃; for 36h; | a) Preparation of N-[2-(ethoxycarbonyl)ethyl]-D-leucine benzyl ester[0191] D- leucine benzyl ester hydrochloride (5g) was dissolved in DMF (30ml) , DIEA (2.6g) was added, ethyl 3-bromopropionate (4.1g) was added dropwisely slowly, and the resulting mixture was allowed to react at 60C for 36h,and concentrated under reduced pressue to remove a great quantity of solvent. Ethyl acetate (20ml) was added, andthe organic phase was washed with saturated sodium hydrogencarbonate solution (50ml33) , 5% KHSO4 solution(50ml33) and water until to be neutral and washed with saturated saline solution (50ml31) , dried over anhydroussodium sulfate, and the filtrate was concentrated to give 1.57g yellow oil, which was purified on a column to give 2.1glight yellow- green oil. The content was 96% (HPLC, mobile phase 1, method 1) .Rf = 0.5Developer: petroleum ether: ethyl acetate = 2: 1Color development: ultraviolet, iodine and 1% ninhydrin solutionMS: 344 (M+Na) |
In ethyl acetate; N,N-dimethyl-formamide; | a) Preparation of N-[2-(ethoxycarbonyl)ethyl]-D-leucine benzyl ester <strong>[68838-94-8]D-leucine benzyl ester hydrochloride</strong> (5 g) was dissolved in DMF (30 ml), DIEA (2.6 g) was added, ethyl 3-bromopropionate (4.1 g) was added dropwisely slowly, and the resulting mixture was allowed to react at 60 C. for 36 h, and concentrated under reduced pressure to remove a great quantity of solvent. Ethyl acetate (20 ml) was added, and the organic phase was washed with saturated sodium hydrogencarbonate solution (50 ml*3), 5% KHSO4 solution (50 ml*3) and water until to be neutral and washed with saturated saline solution (50 ml*1), dried over anhydrous sodium sulfate, and the filtrate was concentrated to give 1.57 g yellow oil, which was purified on a column to give 2.1 g light yellow-green oil. The content was 96% (HPLC, mobile phase 1, method 1). |