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

HRID 1246505노트

반응식

HRID 1246505 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

[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.

후처리

  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

출처 및 근거

ORD 기록
ord-c5d9a900d27946f6a43afbf0e48b094a
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07125901B2

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