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Triethylamine → (trans)-3-[3-(4-Bromo-phenyl)-acryloyl]-4-methyl-5-phenyl-oxazolidin-2-one

HRID 1392695
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HRID 1392695 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2C[C@H:9]2[C:11]([O:13]CC)=O)=[CH:4][CH:3]=1.[CH3:16][C@@H:17]1[C@H:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:20][C:19](=[O:28])[NH:18]1.CCN(CC)CC>CC#N>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH:9][C:11]([N:18]2[C@@H:17]([CH3:16])[C@H:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:20][C:19]2=[O:28])=[O:13])=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 2733812(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinoneHCID 66578655ethyl (1R,2R)-2-(4-bromophenyl)cyclopropanecarboxylate

생성물 1

HCID 69159075(trans)-3-[3-(4-Bromo-phenyl)-acryloyl]-4-methyl-5-phenyl-oxazolidin-2-one

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 3-(4-bromo-phenyl)-1-imidazol-1-yl-propenone (1.05 eq) from Step 1, (4R,5S)-(+)-4-methyl-5-phenyl-2-oxazolidinone (1.0 eq) or (−)-isomer and Et3N (1.2 eq) in CH3CN (0.2M) was refluxed overnight. The resulting mixture was cooled to rt, filtered on a pad of silica gel and concentrated. Crystallization in hexane:Et2O afforded the title compound as a white solid.

후처리

  1. filtrationfiltered on a pad of silica gel
  2. concentrationconcentrated
  3. customCrystallization in hexane

출처 및 근거

ORD 기록
ord-1a8463b735fb4bbfb25d310832674a66
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07342024B2

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