Reaction equation
[CH2:1]([N:4]([CH2:10][S:11]([C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:13])=[O:12])[C:5](=[O:9])[C@@H:6]1[O:8][CH2:7]1)[CH:2]=[CH2:3].[F-].[NH4+].C1COCC1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([N:4]1[C@H:10]([S:11]([C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:13])=[O:12])[C@@H:6]([CH2:7][OH:8])[C:5]1=[O:9])[CH:2]=[CH2:3]Participants
Procedure
A solution of 197 mg (0.757 mmol) of N-allyl-N-tert.-butylsulphonylmethyl-(R)-glycidic acid amide in 1 ml of tetrahydrofuran is introduced at 0°, with the exclusion of moisture, into 8 ml of a tetra-n-butyl; ammonium fluoride/THF solution which has been prepared from 5.0 g of tetra-n-butylammonium fluoride trihydrate by dehydrating at 60° C./0.1 torr and making up to 20 ml with tetrahydrofuran. The reaction mixture is stirred for 2 hours at room temperature and then partitioned between methylene chloride and phosphate buffer solution (pH 8.0). The crude product obtained by drying over sodium sulphate and concentration by evaporation of the organic phase is chromatographed over preparative silica gel plates using hexane/ethyl acetate (1:3). the title compound is obtained in the form of colourless crystals.
Workup
- customby dehydrating at 60° C.
- custompartitioned between methylene chloride and phosphate buffer solution (pH 8.0)
- customThe crude product obtained
- dry with materialby drying over sodium sulphate and concentration by evaporation of the organic phase
- customis chromatographed over preparative silica gel plates
Sources & evidence
- ORD record
- ord-4aba25dbbd1344a8bc8c659123e7942c
- Source dataset
- uspto-grants-1986_09
- Patent number
- US04614614
Linked notes
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