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CAS No. : | 1188263-67-3 | MDL No. : | MFCD04973126 |
Formula : | C9H21ClN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZPISLPKNUNZUJQ-UHFFFAOYSA-N |
M.W : | 224.73 | Pubchem ID : | 45072252 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
90% | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20.0℃; for 0.25h; | <strong>[152548-66-8]Fmoc-N-Me-Asp(tBu)-OH</strong> b1 (6.96 g; 16.36 mmol; 1.00 eq.) was dissolved in DMF (139 ml). PyBOP (12.77 g; 24.54 mmol; 1.50 eq.) and DIPEA (14.25 ml; 81.79 mmol; 5.00 eq.) were added and stirred until dissolved completely. N-Boc-N-methyl-1,3-diaminopropane hydrochloride b2 (4.04 g; 17.99 mmol; 1.10 eq.) was added and the reaction mixture was stirred at room temperature for 15 min. Complete conversion to the product was observed by LCMS. The reaction mixture was diluted with 400 ml of dichloromethane and was washed three times with 400 ml of 0.1 N HCl. The organic layer was washed three times with 400 ml of saturated NaHCO3solution and once with 200 ml of brine. The organic layer was dried over MgSO4, filtered and concentrated. The crude material was dissolved in 14 ml of dichloromethane and purified by normal phase flash chromatography. The product containing fractions were pooled and the solvent was evaporated. The final material was dried under high vacuum to yield amide compound b3 as a white foam. Yield: 8.81 g (14.79 mmol, 90%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h / 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.08 h / 20 °C | ||
Multi-step reaction with 2 steps 1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h / 20 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.08 h / 20 °C 3.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 20 °C 3.2: 1.67 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.2 h / 20 °C 3.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.02 h / 20 °C 3.2: 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.2 h / 20 °C 3.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.02 h / 20 °C 3.2: 2 h / 20 °C 4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.17 h / 20 °C 4.2: 0.02 h / 20 °C |
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