Citric Acid → HCID 15042011, compound
Reaction equation
C(#N)C.[C:4]([C:8]1[CH:9]=[C:10]([S:19][CH2:20][C@H:21]2[O:26][C:25](=[O:27])[CH2:24][C@H:23]([OH:28])[CH2:22]2)[CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])([CH3:7])([CH3:6])[CH3:5].[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:34]>>[C:15]([C:12]1[CH:11]=[C:10]([S:19][CH2:20][C@@H:21]([OH:34])[CH2:22][C@@H:23]([OH:28])[CH2:24][C:25]([OH:26])=[O:27])[CH:9]=[C:8]([C:4]([CH3:7])([CH3:5])[CH3:6])[C:13]=1[OH:14])([CH3:16])([CH3:18])[CH3:17]Participants
Conditions
- Temperature
- -20 °C
Procedure
To 1.6 ml of a solution of acetonitrile containing 150 mg (0.409 mmol) of (4R,6S)-6-[[(3,5-di-tert-butyl-4-hydroxyphenyl)thio]methyl]-4-hydroxytetrahydropyrane-2-one was added 0.98 ml of 1N lithium hydroxide with stirring in an atmosphere of argon at -20° C. After 30 minutes thereto was added 3.9 ml of 0.1 M solution of citric acid, and an organic solvent was distilled away under reduced pressure at a temperature not more than 25° C. In ether was dissolved the residue and the mixture was washed with saturated brine solution, dried and distilled away under reduced pressure to give 157 mg of (3R,5S)-6-[(3,5-di-tert-butyl-4-hydroxyphenyl)thio]-3,5-dihydroxyhexanoic acid. Thereto was added 3.9 ml (0.389 mmol) of 0.1 N sodium hydroxide which was ice-cooled, washed with ether and freeze-dried to give 151 mg of the desired compound (yield: 89%).
Workup
- distillationan organic solvent was distilled away under reduced pressure at a temperature not more than 25° C
- dissolutionIn ether was dissolved the residue
- washthe mixture was washed with saturated brine solution
- customdried
- distillationdistilled away under reduced pressure
Sources & evidence
- ORD record
- ord-dc668a70bcf04c51a449a271606d4bab
- Source dataset
- uspto-grants-1992_03
- Patent number
- US05093363
Reaction notes
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