Reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH2:11]2)=[CH:7][C:6]=1[NH:14][S:15]([C:18]1[S:19][CH:20]=[C:21]([CH3:23])[N:22]=1)(=[O:17])=[O:16].C(P(CCCC)CCCC)CCC.[F:37][C@@H:38]([CH3:41])[CH2:39]O.N(/C(N1CCCCC1)=O)=N\C(N1CCCCC1)=O>C1COCC1>[F:37][C@@H:38]([CH3:41])[CH2:39][N:14]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][C:5]=1[O:4][CH2:3][O:2][CH3:1])[CH2:11][CH2:10][CH2:9]2)[S:15]([C:18]1[S:19][CH:20]=[C:21]([CH3:23])[N:22]=1)(=[O:17])=[O:16]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
896 mg of N-[6-(methoxymethoxy)-2,3-dihydro-1H-inden-5-yl]-4-methyl-1,3-thiazole-2-sulfonamide, 665 mg of tributyl phosphine, and 257 mg of (2S)-2-fluoropropan-1-ol were dissolved in 8.96 mL of THF, and 829 mg of 1,1′-[(E)-diazen-1,2-diyldicarbonyl]dipiperidine was added thereto, followed by stirring overnight at room temperature. After the insoluble materials were removed by filtration, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10 to 50:50) to obtain 632 mg of N-[(2S)-2-fluoropropyl]-N-[6-(methoxymethoxy)-2,3-dihydro-1H-inden-5-yl]-4-methyl-1,3-thiazole-2-sulfonamide.
Workup
- customAfter the insoluble materials were removed by filtration
- concentrationthe filtrate was concentrated under reduced pressure
- customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10 to 50:50)
Sources & evidence
- ORD record
- ord-35ad8660e8664d61bd5bd05f70e8665a
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08314240B2
Linked notes
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