Reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:45]([N:48]([CH2:54][S:55]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)(=[O:57])=[O:56])[C:49](=[O:53])[C@@H:50]1[O:52][CH2:51]1)[CH:46]=[CH2:47]>O1CCCC1>[CH2:45]([N:48]1[C@H:54]([S:55]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)(=[O:57])=[O:56])[C@@H:50]([CH2:51][OH:52])[C:49]1=[O:53])[CH:46]=[CH2:47]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
8 ml of a tetra-n-butylammonium fluoride/THF solution which has been prepared from 5 g of tetra-n-butylammonium fluoride trihydrate by drying at 60°/0.1 torr and making up to 20.0 ml with tetrahydrofuran is added to a solution of 201 mg (0.757 mmol) of N-allyl-N-phenylsulphonylmethyl-(R)-glycidic acid amide in 1 ml of tetrahydrofuran. The resulting reaction mixture is stirred for 2 hours at 0° and then partitioned between methylene chloride and phosphate buffer solution having a pH of 8.0. The crude product isolated from the organic layer by means of concentration by evaporation is chromatographed over preparative silica gel plates in ethyl acetate/hexane (2:1) and the title compound is obtained in the form of a colourless oil.
Workup
- customby drying at 60°/0.1 torr
- customThe resulting reaction mixture
- custompartitioned between methylene chloride and phosphate buffer solution
- customThe crude product isolated from the organic layer by means of concentration by evaporation
- customis chromatographed over preparative silica gel plates in ethyl acetate/hexane (2:1)
Sources & evidence
- ORD record
- ord-ca824bbc1c4944458d3aa5974f6984c1
- Source dataset
- uspto-grants-1986_09
- Patent number
- US04614614
Linked notes
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