Hydrochloric Acid → 5-[1-Fluoro-3-hydroxy-7-(4-formyl-4-methyl-pentyl)-naphthalen-2-yl]-1,1-dioxo-[1,2,5]thiadiazolidin-3-one
Reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH2:13][CH2:14][C:15]([CH3:19])([CH3:18])[CH2:16][OH:17])[CH:10]=2)[CH:5]=[C:4]([OH:20])[C:3]=1[N:21]1[S:25](=[O:27])(=[O:26])[NH:24][C:23](=[O:28])[CH2:22]1.C(N(CC)CC)C.O.Cl>CS(C)=O>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH2:13][CH2:14][C:15]([CH:16]=[O:17])([CH3:19])[CH3:18])[CH:10]=2)[CH:5]=[C:4]([OH:20])[C:3]=1[N:21]1[S:25](=[O:26])(=[O:27])[NH:24][C:23](=[O:28])[CH2:22]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 5-[1-fluoro-3-hydroxy-7-(5-hydroxy-4,4-dimethylpentyl)-naphthalen-2-yl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one (1.00 g, 2.23 mmol) in anhydrous DMSO (10 ml) at room temperature was added triethylamine (2.17 mL, 15.6 mmol) followed by a slow addition of a solution of sulfur trioxide pyridine complex (1.28 g, 8.02 mmol) in anhydrous DMSO (12 mL). The reaction mixture was stirred for 30 min and cold water (70 mL) was slowly added. The above content was acidified with 3 N HCl to pH 2.5, extracted twice with EtOAc, washed with brine, dried over MgSO4, and concentrated to yield the title compound as a light brown solid. Retention time=1.22 min (Method A); MS (M−H)−=407.
Workup
- extractionextracted twice with EtOAc
- washwashed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-23016b81fa0b43678f342aa48249d70f
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08252820B2
Reaction notes
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