Dimethyl Sulfoxide → HCID 68907555, compound
Reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([O:15][C:16]([NH:18][C@@H:19]1[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][C@@H:20]1[NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl.O1CCCC1.O>[C:11]([O:15][C:16]([NH:18][C@@H:19]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][C@@H:20]1[NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:17])([CH3:14])([CH3:13])[CH3:12]Participants
Conditions
- Temperature
- -40 °C
Procedure
Dimethylsulfoxide (6.8 ml) was added to a solution of oxalyl chloride (8.2 ml) in dichloromethane (100 ml) at −60° C., and a solution of (1R*,2S*)-N1,N2-bis(tert-butoxycarbonyl)-4-hydroxy-1,2-cyclohexanediamine (mixture of stereoisomers) (6.32 g) in tetrahydrofuran (80 ml) was added at a time, and the mixture was stirred for 1 hour. The temperature of the mixture was raised to −40° C., and triethylamine (21 ml) was added. The mixture was heated to room temperature. After 3 hours, the reaction mixture was poured into water and extracted with dichloromethane. The resultant organic layer was washed with saturated saline and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1) to obtain the title compound (3.8 g) as a pale yellow solid.
Workup
- temperatureThe mixture was heated to room temperature
- waitAfter 3 hours
- extractionextracted with dichloromethane
- washThe resultant organic layer was washed with saturated saline
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1)
Sources & evidence
- ORD record
- ord-6fb3f12f87a947bda5476055431e6a10
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935824B2
Reaction notes
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