Sodium Thiosulfate → HCID 86715651, compound
Reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH:24]([C:36]1[N:40]([CH3:41])[N:39]=[N:38][CH:37]=1)[CH:25]1[CH2:28][N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:26]1.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl.O>[CH3:41][N:40]1[C:36]([C:24]([CH:25]2[CH2:28][N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:26]2)=[O:23])=[CH:37][N:38]=[N:39]1Participants
Conditions
- Temperature
- 23 °C
Procedure
Dess-Martin periodinane (10.9 g, 25.7 mmol) was added in one portion to a stirring solution of tert-butyl 3-(hydroxy(1-methyl-1H-1,2,3-triazol-5-yl)methyl)azetidine-1-carboxylate (4.60 g, 17.1 mmol, Intermediate 59: step a) in dry dichloromethane (86 mL). The resulting mixture was stirred at 23° C. After 18 h, a mixture containing equal parts water, saturated aqueous sodium thiosulfate solution, and saturated aqueous sodium bicarbonate solution was added (200 mL). Dichloromethane (100 mL) was added. The resulting biphasic mixture was stirred for 15 min. The layers were separated. The organic layer was dried with sodium sulfate and the dried solution was concentrated. The residue was purified by flash-column chromatography on silica gel eluting with dichloromethane initially, grading to 5% methanol-dichloromethane to provide the title compound as a clear, colorless oil.
Workup
- additionwas added (200 mL)
- stirringThe resulting biphasic mixture was stirred for 15 min
- customThe layers were separated
- dry with materialThe organic layer was dried with sodium sulfate
- concentrationthe dried solution was concentrated
- customThe residue was purified by flash-column chromatography on silica gel eluting with dichloromethane initially
Sources & evidence
- ORD record
- ord-d666058d26384825abd8429a85d8ae72
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09290476B2
Reaction notes
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