Reaction equation
C([NH:4][C:5](=[CH:9][CH2:10][PH:11]([CH2:13]O)=[O:12])[C:6]([OH:8])=[O:7])(=O)C.[ClH:15].C[OH:17]>>[ClH:15].[ClH:15].[NH2:4][C@H:5]([C:6]([OH:8])=[O:7])[CH2:9][CH2:10][P:11]([CH3:13])(=[O:17])[OH:12]Participants
Procedure
0.0087 g (0.019 mmol) of chloronorbornadienerhodium(I) dimer and 0.022 g (0.053 mmol) of the compound Va are dissolved in 5 ml of methanol under an atmosphere of argon. The catalyst solution obtained is added under argon to a solution of 2.21 g (0.01 mol) of 2-acetamido-4-(hydroxymethylphosphinyl)-2-butenoic acid in 45 ml of methanol. The reaction vessel is evacuated, then hydrogenation is performed at a pressure of 3.0 bar. After a reaction time of 44 hours, the reaction vessel is depressurized, the reaction mixture evaporated down, the residue taken up in water and the precipitated catalyst separated off. As a result of adding an equivalent quantity of concentrated hydrochloric acid to the filtrate, a 6N hydrochloric acid solution is prepared which is boiled under reflux for 12 hours. After evaporating this solution down, 2.0 g (91.9% of theory) of L-homoalanin-4-yl(methyl)phosphinic acid hydrochloride is obtained as a white solid which is purified by recrystallization from an ethanol/water mixture.
Workup
- customThe catalyst solution obtained
- customThe reaction vessel is evacuated
- customAfter a reaction time of 44 hours
- customthe reaction mixture evaporated down
- customthe precipitated catalyst separated off
- customAs a result
- temperatureunder reflux for 12 hours
- customAfter evaporating this solution down
Sources & evidence
- ORD record
- ord-3b5954c9604849f1b2b973f418798d61
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04922006
Linked notes
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