Chloroform → HCID 23156132, compound
Reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]3[C:23]4=[N:24][C:25]([CH3:29])=[CH:26][C:27]([CH3:28])=[C:22]4[N:21]=[C:20]3[CH2:30][CH3:31])=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)C.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+].C(Cl)(Cl)Cl>C1COCC1>[CH2:30]([C:20]1[N:19]([CH2:18][C:15]2[CH:16]=[CH:17][C:12]([NH:11][C:8]3[CH:7]=[CH:6][C:5]([CH2:4][OH:3])=[CH:10][CH:9]=3)=[CH:13][CH:14]=2)[C:23]2=[N:24][C:25]([CH3:29])=[CH:26][C:27]([CH3:28])=[C:22]2[N:21]=1)[CH3:31]Participants
6
Procedure
Compound 99 (0.453 mg, 1.06 mmol) was dissolved in THF (10 mL), and a diisobutylaluminum hydride-toluene solution (1 mmol/L, 4.2 mL, 4.2 mmol) was added to the solution, followed by stirring at room temperature for 10 minutes. The reaction mixture was added with an aqueous potassium sodium tartrate solution and chloroform, followed by stirring at room temperature for 4 hours, then the mixture was extracted with chloroform three times. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The residue was recrystallized from ethanol to obtain Compound 101 (0.384 g, 0.994 mmol, yield 94%).
Workup
- stirringby stirring at room temperature for 4 hours
- extractionthe mixture was extracted with chloroform three times
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was recrystallized from ethanol
Sources & evidence
- ORD record
- ord-00ce80b31551451385f59964a946b576
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507484B2
Reaction notes
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