4-Toluenesulfonyl chloride → HCID 86707004, compound
Reaction equation
[N:1]1([C:5]2[S:6][C@H:7]3[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C@H:10]([OH:17])[C@H:8]3[N:9]=2)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>CN(C=O)C>[CH3:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([O:15][CH2:14][C@H:12]2[O:13][C@H:7]3[C@H:8]([N:9]=[C:5]([N:1]4[CH2:4][CH2:3][CH2:2]4)[S:6]3)[C@@H:10]([OH:17])[C@@H:11]2[OH:16])(=[O:34])=[O:33])=[CH:28][CH:27]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (3aR,5R,6S,7R,7aR)-2-(azetidin-1-yl)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol (5.0 g, 19 mmol) and triethylamine (3.88 g, 38 mmol) in DMF (50 mL) was treated with 4-methylbenzene-1-sulfonyl chloride (4.4 g, 23 mmol) overnight at room temperature. The reaction mixture was quenched by water (100 mL), extracted with dichloromethane (3×80 mL), washed with brine (3×50 mL), dried over anhydrous magnesium sulfate, and concentrated under vacuum to give a residue, which was purified by a silica gel column eluted with 1%-5% methanol in dichloromethane to give crude compound 4 as a light yellow solid (1.0 g). This material was employed in the next step without further purification. (ES, m/z) [M+H]+ 415.0.
Workup
- customThe reaction mixture was quenched by water (100 mL)
- extractionextracted with dichloromethane (3×80 mL)
- washwashed with brine (3×50 mL)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under vacuum
- customto give a residue, which
- customwas purified by a silica gel column
- washeluted with 1%-5% methanol in dichloromethane
Sources & evidence
- ORD record
- ord-c9eb97e933224e05bdac8fa037ea7080
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933040B2
Reaction notes
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