Methanesulfonyl chloride → 4-{[1-Azido-3-(phenylsulfanyl)propan-2-yl]amino}-3-nitrobenzene-1-sulfonamide
Reaction equation
O[CH2:2][CH:3]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][C:14]=1[N+:23]([O-:25])=[O:24])[CH2:4][S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)C(C)C)(C)C.CS(Cl)(=O)=O.[N-:40]=[N+:41]=[N-:42].[Na+]>ClCCl.CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[N:40]([CH2:2][CH:3]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][C:14]=1[N+:23]([O-:25])=[O:24])[CH2:4][S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[N+:41]=[N-:42]Participants
9
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 50 °C
Procedure
A solution of Example 434B (1.01 g, 2.6 mmol) and N,N-diisopropylethylamine (0.70 mL, 4.0 mmol) in dichloromethane (5 mL) and DMF (5 mL) at room temperature was treated with methanesulfonyl chloride (0.22 mL, 2.90 mmol), stirred for 1 hour, and concentrated to remove the dichloromethane. The resulting DMF solution was treated with sodium azide (1.95 g, 30 mmol) and tetrabutylammonium iodide (100 mg), heated to 50° C. for 16 hours, diluted with ethyl acetate (200 mL), washed with water (100 mL) and brine (50 mL), dried (MgSO4), filtered, and concentrated to provide the desired product.
Workup
- concentrationconcentrated
- customto remove the dichloromethane
- washwashed with water (100 mL) and brine (50 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6d657df872c74f6bb22c1da49afa66bb
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06720338B2
Reaction notes
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