Triphenylphosphine → HCID 21942891, compound
Reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[C:15]([N:18]1[C:22]2[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:21]=2[S:20][CH:19]1[C:28]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:29]=1[OH:36])(=[O:17])[CH3:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:56]1([CH3:71])[CH:61]=[CH:60][C:59]([S:62]([O:65][CH2:66][CH2:67][CH:68]([CH3:70])O)(=[O:64])=[O:63])=[CH:58][CH:57]=1>O1CCCC1>[C:15]([N:18]1[C:22]2[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:21]=2[S:20][CH:19]1[C:28]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:29]=1[O:36][CH:68]([CH3:70])[CH2:67][CH2:66][O:65][S:62]([C:59]1[CH:58]=[CH:57][C:56]([CH3:71])=[CH:61][CH:60]=1)(=[O:63])=[O:64])(=[O:17])[CH3:16]Participants
6
Procedure
A solution of diisopropyl azodicarboxylate (1.54 g, 7.61 mmol) in anhydrous tetrahydrofuran (10 ml) was added to a solution of 3-acetyl-6-chloro-2-(2-hydroxy-5-methoxyphenyl)benzothiazoline (2.56 g, 7.62 mmol), triphenylphosphine (2.00 g, 7.61 mmol) and 3-p-toluenesulfonyloxy-1-methylpropanol (1.86 g, 7.61 mmol) in anhydrous tetrahydrofuran (10 ml) at room temperature, and the mixture was stirred for four hours. The reaction mixture was concentrated, and the obtained oily matter was purified by silica gel column chromatography (mobile phase:hexane/ethyl acetate=4/1) to give 1.58 g (37%) of the target compound.
Workup
- concentrationThe reaction mixture was concentrated
- customthe obtained oily matter was purified by silica gel column chromatography (mobile phase:hexane/ethyl acetate=4/1)
Sources & evidence
- ORD record
- ord-426b8d64c8c04aa9b1560aa84378c4af
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07410987B2
Reaction notes
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