Hydrochloric Acid → HCID 23717340, compound
Reaction equation
[OH-:1].[Na+:2].[CH3:3][C@@H:4]([CH2:29][CH2:30][CH3:31])[C:5]([O:7][C@@H:8]1[C@H:17]2[C:12]([CH:13]=[CH:14][C@H:15]([CH3:28])[C@@H:16]2[CH2:18][CH2:19][C@H:20]2[O:25][C:24](=[O:26])[CH2:23][C@H:22](O)[CH2:21]2)=[CH:11][CH2:10][CH2:9]1)=[O:6].[OH2:32].Cl>O1CCOCC1>[OH:1][C@H:22]([CH2:21][C@H:20]([OH:25])[CH2:19][CH2:18][C@@H:16]1[C@@H:17]2[C:12](=[CH:11][CH2:10][CH2:9][C@@H:8]2[O:7][C:5](=[O:6])[C@@H:4]([CH3:3])[CH2:29][CH2:30][CH3:31])[CH:13]=[CH:14][C@@H:15]1[CH3:28])[CH2:23][C:24]([O-:26])=[O:32].[Na+:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
0.1 ml of a 0.1N aqueous solution of sodium hydroxide was added to a solution of 10 mg of (4R,6R)-6-{2-[(1S,2S,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-[(S)-2-methylvaleryloxy]-2-methyl-1-naphthyl]ethyl}-tetrahydro-4-hydroxy-2H-pyran-2-one [prepared as described in Example 85, above] in 0.2 ml of 1,4-dioxane, and the mixture was heated at 60° C. for 30 minutes. At the end of this time, 10 ml of water were added to the mixture and the pH of the mixture was adjusted to pH 8.5 with the addition of an appropriate amount of a 0.1N solution of aqueous hydrogen chloride. The resulting mixture was then adsorbed onto a column containing 5 ml of Diaion HP-20™. The resin was washed with 20 ml of water and then eluted with a 60% w/v aqueous acetone solution. The resulting eluate was concentrated by evaporation under reduced pressure, using a rotary evaporator, and the concentrate was lyophilized to give 9.8 mg of the title compound.
Workup
- additioncontaining 5 ml of Diaion HP-20™
- washThe resin was washed with 20 ml of water
- washeluted with a 60% w/v aqueous acetone solution
- concentrationThe resulting eluate was concentrated by evaporation under reduced pressure
- customa rotary evaporator
Sources & evidence
- ORD record
- ord-b89d76b10e2f4938a470812008deda8b
- Source dataset
- uspto-grants-1995_09
- Patent number
- US05451688
Reaction notes
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