Potassium bisulfate → HCID 131720341, compound
Reaction equation
[CH3:1][CH:2]([CH2:4][C@H:5]([NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C:6]([OH:8])=[O:7])[CH3:3].[NH2:20][C@H:21]([C:26]([OH:28])=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24].CN(OC)[C:31](=[O:37])[C@H:32]([CH2:34][CH2:35][CH3:36])[NH2:33].[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)[O-].[K+]>O1CCCC1.O>[CH3:3][CH:2]([CH2:4][C@H:5]([NH:9][C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11])[C:6]([OH:8])=[O:7])[CH3:1].[NH2:20][C@H:21]([C:26]([OH:28])=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24].[NH2:33][C@H:32]([CH:31]=[O:37])[CH2:34][CH2:35][CH3:36]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
A solution of Z-L-leucine-L-leucine-L-norvaline N,O-dimethylhydroxylamide (1.09 g) was dissolved in 20 mL dry tetrahydrofuran (THF) and cooled to 0° C. Lithium aluminum hydride (1M solution in THF, 3.05 mL) was added and the mixture was stirred at 0° C. for 25 minutes. Potassium bisulfate (465 mg) in 20 mL water was added and the mixture was extracted with EtOAc (3×80 mL). The combined organic layers were washed with aqueous 5% HCl, saturated NaHCO3, and brine, then dried over anhydrous MgSO4, filtered, and evaporated to afford the product (430 mg) as a white solid.
Workup
- extractionthe mixture was extracted with EtOAc (3×80 mL)
- washThe combined organic layers were washed with aqueous 5% HCl, saturated NaHCO3, and brine
- dry with materialdried over anhydrous MgSO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-76ce7179f8214eaab1f58645a7a80887
- Source dataset
- uspto-grants-1997_12
- Patent number
- US05693617
Reaction notes
Loading…