Sulfuric acid magnesium salt (1:1) → HCID 86741372, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].[C:13](=[C:16]([OH:21])[C@H:17]([OH:20])[CH:18]=O)([CH3:15])[CH3:14].S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][N:6]=[CH:18][C@H:17]([C:16](=[C:13]([CH3:15])[CH3:14])[OH:21])[OH:20]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution, stirred at room temperature, of 0.9 g (5.4 mmol) of 2,4-dimethoxybenzylamine in 100 ml of methylene chloride are added 3 g of molecular sieve 4Å and, after 20 minutes, 0.7 g (5.4 mmol) of isopropylidene-L-glyceraldehyde and 5 g of anhydrous magnesium sulphate. The mixture is subsequently stirred at room temperature for 1 hour. The organic solution of isopropylidene-L-glyceraldehyde (2,4-dimethoxybenzyl)imine obtained is cooled to -20° C. under argon and treated while stirring with 0.88 ml (5.4 mmol) of triethylamine. A solution of 1.25 g (5.6 mmol) of phthaloylglycyl chloride in 20 ml of dry methylene chloride is then added dropwise within 1 hour and the mixture is subsequently stirred at room temperature overnight. The mixture is washed three times with 100 ml of water each time and with 100 ml of sodium chloride solution and then dried over sodium sulphate. The organic solution is evaporated and the residue is chromatographed on silica gel (230-400 mesh) while eluting with hexane/ethyl acetate (1:1). There are obtained 1.77 g (70%) of N-[(3S,4S)-cis-1-(2,4-dimethoxybenzyl)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-3-azetidinyl]phthalimide as a foam; [α]D =+41° (c=0.8 in chloroform); MS: 466 (M+).
Workup
- additionare added 3 g of molecular sieve 4Å
Sources & evidence
- ORD record
- ord-f880f2d53cd64b7e8888e1149cff19cd
- Source dataset
- uspto-grants-1990_08
- Patent number
- US04948898
Reaction notes
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