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CAS No. : | 5044-52-0 | MDL No. : | MFCD00011807 |
Formula : | C20H18BrP | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VRAYVWUMBAJVGH-UHFFFAOYSA-M |
M.W : | 369.23 | Pubchem ID : | 2723893 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 | UN#: | N/A |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
The procedure described in Synthesis, 301 (1989) was used to prepare amine 13. Aminoalcohol was treated with n-butyllithium to generate the lithium alkoxide which was then added to commercially available vinyltriphosphonium bromide to obtain 1 The two benzyl protecting groups were removed under standard hydrogeneolysis conditions in the presence of acid to afford the primary amine (13). This was coupled with commercially available BOC-protected N-methylglycine using carbonyldiimidazole to afford amide 14 which was treated with dry hydrogen chloride in ethereal solvent to remove the BOC protecting group. The guanidine group was inserted using the commercially available N-pyrazole reagent to afford Compound B-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.92 g | With n-butyllithium; In tetrahydrofuran; at 20℃; for 24h; | To a solution of triphenyl(vinyl)phosphonium bromide (1 .62 g, 4.38 mmol) and tert-butyl 3- (2-hydroxyethoxy)propanoate (1.24 g, 6 mmol) in dry THF (15 mL) was added 2.5 M butyllithium (0.18 mL, 0.44 mmol). The resulting reaction was stirred at room temperature. After 24 h the reaction mixture was quenched with MeOH (5 mL) and concentrated under reduced pressure. The resulting residue was purified by chromatography eluting with 0- 10% MeOH/0.7 M NH3in DCM to give (2-{2-[3-(tert-butoxy)-3- oxopropoxy]ethoxy}ethyl)triphenylphosphonium bromide (0.92 g) as a sticky opague oil, which was used in the next step without any further purification. |