Potassium Hydroxide → HCID 53991866, compound
Reaction equation
[OH:1][C@@H:2]([C@H:8]([OH:25])[C:9](=[O:24])[NH:10][C@H:11]([C:16](=[O:23])[NH:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:12][CH:13]([CH3:15])[CH3:14])[C:3]([O:5]CC)=[O:4].[OH-].[K+]>CO>[OH:1][C@@H:2]([C@H:8]([OH:25])[C:9](=[O:24])[NH:10][C@H:11]([C:16](=[O:23])[NH:17][CH2:18][CH2:19][CH:20]([CH3:21])[CH3:22])[CH2:12][CH:13]([CH3:14])[CH3:15])[C:3]([OH:5])=[O:4]Participants
Conditions
- Temperature
- 0 °C
Procedure
Ethyl (2S,3S)-2,3-dihydroxy-3-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]propionate (309 mg) obtained in Example 2 was dissolved in methanol. 2N KOH (472 μl) was added to the resultant solution, and the solution was stirred at 0° C. for two hours. Thereafter, the solvent was distilled off under reduced pressure, sodium bicarbonate solution was added to adjust the pH to be about 8, and the aqueous layer was washed with ethyl acetate. Subsequently, the pH was adjusted to about 2 with dilute hydrochloric acid, sodium chloride was added until the solution was saturated, and the aqueous layer was extracted with ethyl acetate. The extracted organic layer was washed with sodium chloride solution and dried with magnesium sulfate, and the solvent was distilled off under reduced pressure, thereby obtaining 264 mg of a target compound. NMR data of the compound were as follows.
Workup
- distillationThereafter, the solvent was distilled off under reduced pressure, sodium bicarbonate solution
- additionwas added
- washthe aqueous layer was washed with ethyl acetate
- additionwas added until the solution
- extractionthe aqueous layer was extracted with ethyl acetate
- washThe extracted organic layer was washed with sodium chloride solution
- dry with materialdried with magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-a920d4d7f27e4e8dbe2c1de5be19ee22
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05214056
Reaction notes
Loading…