HCID 178477758, compound → 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,4-dihydroxy-2(5H)-furanone
Reaction equation
[CH2-:1][C:2]([CH3:4])=O.[O:5]=[CH:6][C@H:7]([CH2:9][OH:10])[OH:8].[CH2-]C(C)=O.COC1C=C(OC)C=CC=1CN=C(C)[CH2-].[O:30]=[CH:31][C@H:32]([CH2:34][OH:35])[OH:33]>>[CH3:1][C:2]1([CH3:4])[O:8][CH:7]([CH:9]2[O:10][C:31](=[O:30])[C:32]([OH:33])=[C:34]2[OH:35])[CH2:6][O:5]1Participants
Procedure
In 400 ml of pure water was suspended 43.2 g of 5,6-O-isopropylidene-L-ascorbic acid, and 40 g of calcium carbonate was added. The mixture was cooled and 80 ml of 30% aqueous hydrogen peroxide was added dropwise while maintaining the temperature at 10° C. or below. Thereafter, the temperature was raised to 20° C. over a period of an hour, followed by stirring at the same temperature for 2 hours and at 30° to 35° C. for 30 minutes. To the reaction mixture were portionwise added 8 g of activated carbon and 1 g of 10 w/w % palladium-on-carbon (50 w/w % hydrous) to treat the unreacted hydrogen peroxide therewith and the mixture was cooled, followed by removal of the insoluble substance with the aid of Hyflo Super-Cel to give 650 ml of an aqueous solution containing CIT. Thereafter, according to the procedure of Example 2 there was synthesized (S)-glyceraldehyde acetonide and the acetonide was then converted to (S)-glyceraldehyde acetonide 2,4-dimethoxybenzylimine. The yield of the imine was 39.3 g (70% overall yield from 5,6-O-isopropylidene-L-ascorbic acid).
Workup
- additioncontaining CIT
Sources & evidence
- ORD record
- ord-0cba12a6af83460092ae5e54a23e5d26
- Source dataset
- uspto-grants-1986_01
- Patent number
- US04567282
Reaction notes
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