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CAS No. : | 16012-70-7 | MDL No. : | MFCD00037234 |
Formula : | C14H18N2O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JBGCVTHXXTVYIP-UWVGGRQHSA-N |
M.W : | 294.30 | Pubchem ID : | 7009583 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
92.2% | With water; lithium hydroxide; In tetrahydrofuran; at 0℃; for 10h; | <strong>[2483-51-4]Cbz-L-Ala-L-Ala-OMe</strong> (100 g, 0.34 mol) was dissolved in a mixed solution of tetrahydrofuran (2 L) and water (1 L) and cooled to 0 C. 1 mol/L lithium hydroxide solution (400 mL) was dropped to the mixture and then stirred and reacted for 10 hours. Concentrated hydrochloric acid was dropped to the mixture to neutralize its pH to below 6. Tetrahydrofuran was removed by evaporation under reduced pressure. The residual water phase was extracted by dichloromethane (1 L*3). The organic phase was dried with anhydrous sodium sulfate and removed by evaporation under reduced pressure to obtain a white solid II, i.e., Cbz-Ala-Ala-OH (88 g; Yield, 92.2%). |
92.2% | With water; lithium hydroxide; In tetrahydrofuran; at 0℃; for 10h; | [0084] N-(N-benzyloxycarbonyl-L-alanyl)-L-Ala methyl ester (100g, 0.34mol) were dissolved in a mixed solution of tetrahydrofuran (2L) and water (1L). The mixture was cooled to 0C and 1M lithium hydroxide solution (400mL) were dropped into the mixture. The resultant mixture was stirred for reaction for 10 hours. Concentrated hydrochloric acid was dropped to adjust the pH to be less than 6. Most of tetrahydrofuran were removed by rotary evaporation. The residual water phase was extracted by dichloromethane (1L*3). The organic phase was dried by anhydrous sodium sulphate. A white solid II was obtained after vaporizing and drying under reduced pressure (88g; Yield, 92.2%). |
92.2% | With water; lithium hydroxide; In tetrahydrofuran; at 0℃; for 10h; | <strong>[2483-51-4]Cbz-L-Ala-L-Ala-OMe</strong> (100 g, 0.34 mol) was dissolved in a mixed solution of tetrahydrofuran (2 L) and water (1 L) and cooled to 0 C. 1 mol/L lithium hydroxide solution (400 mL) was dropped to the mixture and then stirred and reacted for 10 hours. Concentrated hydrochloric acid was dropped to the mixture to neutralize its pH to below 6. Tetrahydrofuran was removed by evaporation under reduced pressure. The residual water phase was extracted by dichloromethane (1 L*3). The organic phase was dried with anhydrous sodium sulfate and removed by evaporation under reduced pressure to obtain a white solid II, i.e., Cbz-Ala-Ala-OH (88 g; Yield, 92.2%). |
With lithium hydroxide; In tetrahydrofuran; water; at 0℃; for 3h; | General procedure: The dipeptide 12a-v (1.0 eq) was dissolved in THF:H2O (4:1, 10 mL) and LiOH (1.2 equiv) was added at 0 C. The mixture was stirred at 0 C for 3 hours before acidifying with 1 M HCl (2 mL) to < pH 3. The aqueous phase was extracted with EtOAc (3 X 5 mL), dried over sodium sulfate, filtered, and concentrated to yield 13a-v, which were confirmed by MS then carried directly into the final step. |