[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromide → methyl 4-((Z)-2-(2-(acetylamino)-5-[4-(methylthio)benzyl]-1,3-thiazol-4-yl)vinyl)benzoate

HRID 2117915Notes

Reaction equation

HRID 2117915 reaction equation
[Br-].[CH3:2][O:3][C:4]([C:6]1[CH:31]=[CH:30][C:9]([CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:8][CH:7]=1)=[O:5].CC(C)([O-])C.[K+].[CH:38]([C:40]1[N:41]=[C:42]([NH:54][C:55](=[O:57])[CH3:56])[S:43][C:44]=1[CH2:45][C:46]1[CH:51]=[CH:50][C:49]([S:52][CH3:53])=[CH:48][CH:47]=1)=O>CN(C=O)C>[C:55]([NH:54][C:42]1[S:43][C:44]([CH2:45][C:46]2[CH:47]=[CH:48][C:49]([S:52][CH3:53])=[CH:50][CH:51]=2)=[C:40](/[CH:38]=[CH:10]\[C:9]2[CH:8]=[CH:7][C:6]([C:4]([O:3][CH3:2])=[O:5])=[CH:31][CH:30]=2)[N:41]=1)(=[O:57])[CH3:56]

Participants

5

Reactant 3

HCID 2764257[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromideHCID 21914849N-{4-formyl-5-[4-(methylthio)benzyl]-1,3-thiazol-2-yl}acetamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 86595605methyl 4-((Z)-2-(2-(acetylamino)-5-[4-(methylthio)benzyl]-1,3-thiazol-4-yl)vinyl)benzoateYield 96.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromide (4.81 g) and DMF (60 ml) were combined under N2 atmosphere. Then potassium tert-butoxide (1.32 g) and N-{4-formyl-5-[4-(methylthio)benzyl]-1,3-thiazol-2-yl}acetamide (3 g) were added to the suspension at 0° C. The reaction mixture was stirred at r.t. for 18 hours, poured into ice-water, and extracted with AcOEt. The organic layer was washed with water and brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel with CHCl3/AcOEt (2:1) as an eluent. The solid was suspended in AcOEt, and the suspension was filtered. The filtrate was concentrated in vacuo to give methyl 4-((Z)-2-(2-(acetylamino)-5-[4-(methylthio)benzyl]-1,3-thiazol-4-yl}vinyl)benzoate (4.16 g) as a yellow amorphous substance.

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography over silica gel with CHCl3/AcOEt (2:1) as an eluent
  6. filtrationthe suspension was filtered
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2a17b97ad92f44d1a219ddd73c8f44a8
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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