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Chlorotrimethylsilane → (S)-4-benzyl-3-((2R,3S)-3-(3-bromophenyl)-2-methyl-3-(trimethylsilyloxy)propanoyl)oxazolidin-2-one

HRID 1021154
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HRID 1021154 반응식
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:17])[CH2:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg+2].[Cl-].[Cl-].[Br:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=[O:26].Cl[Si:31]([CH3:34])([CH3:33])[CH3:32]>CCOC(C)=O.CCN(CC)CC>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:17])[C@H:15]([CH3:16])[C@@H:25]([C:24]1[CH:27]=[CH:28][CH:29]=[C:22]([Br:21])[CH:23]=1)[O:26][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 6397ChlorotrimethylsilaneHCID 765833-BromobenzaldehydeHCID 2733696(4S)-4-Benzyl-3-propanoyl-1,3-oxazolidin-2-oneHCID 5360315Magnesium Chloride

생성물 1

HCID 66743729(S)-4-benzyl-3-((2R,3S)-3-(3-bromophenyl)-2-methyl-3-(trimethylsilyloxy)propanoyl)oxazolidin-2-one

시약·촉매·용매 2

HCID 8471
Triethylamine
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of (S)-4-benzyl-3-propionyloxazolidin-2-one, anhydrous MgCl2 (0.104 g, 1.09 mmol) and 3-bromobenzaldehyde in EtOAc is added Et3N followed by chlorotrimethylsilane. The reaction mixture is stirred under argon at room temperature for 24 h and then filtered through a layer of a silica gel, washing with EtOAc. The combined filtrates are concentrated under reduced pressure and the residue is purified by flash chromatography (1 to 30% EtOAc/hexane gradient) to give (S)-4-benzyl-3-((2R,3S)-3-(3-bromophenyl)-2-methyl-3-(trimethylsilyloxy)propanoyl)oxazolidin-2-one.

후처리

  1. filtrationfiltered through a layer of a silica gel
  2. washwashing with EtOAc
  3. concentrationThe combined filtrates are concentrated under reduced pressure
  4. customthe residue is purified by flash chromatography (1 to 30% EtOAc/hexane gradient)

출처 및 근거

ORD 기록
ord-d7369fd2ac6e4963a4d41a03a585b6bc
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08716529B2

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