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Triethylsilane → (S)-4-Benzyl-3-(3-{2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-2-(2S)-methoxy-propionyl)-oxazolidin-2-one

HRID 1394749
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HRID 1394749 반응식
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:51])[C@@H:15]([O:49][CH3:50])[C@@H:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][C:27]2[N:28]=[C:29]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[O:30][C:31]=2[CH3:32])=[CH:20][C:19]=1[O:39][Si:40]([CH3:48])([CH3:47])[C:41]([CH3:46])([CH3:45])[CH:42]([CH3:44])[CH3:43])O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:51])[C@@H:15]([O:49][CH3:50])[CH2:16][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][C:27]2[N:28]=[C:29]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[O:30][C:31]=2[CH3:32])=[CH:20][C:19]=1[O:39][Si:40]([CH3:47])([CH3:48])[C:41]([CH3:45])([CH3:46])[CH:42]([CH3:43])[CH3:44])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 12052TriethylsilaneHCID 69280419(S)-4-Benzyl-3-((2S,3R)-3-{2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-3-hydroxy-2-methoxy-propionyl)-oxazolidin-2-one

생성물 1

HCID 69283498(S)-4-Benzyl-3-(3-{2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-2-(2S)-methoxy-propionyl)-oxazolidin-2-one

시약·촉매·용매 1

HCID 6422
Trifluoroacetic acid
용매

실험 절차

The above prepared (S)-4-benzyl-3-((2S,3R)-3-{2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-3-hydroxy-2-methoxy-propionyl)-oxazolidin-2-one (2.8 g, 3.91 mmol) was dissolved in 10 ml of trifluoroacetic acid, treated at 0° C. with 10 ml of triethylsilane and then kept for 3 hours at ambient temperature. The reaction mixture was then poured onto crashed ice/AcOEt/NaOH (1M), the organic layer was washed with water and brine, dried over magnesium sulfate and evaporated to dryness. Flash chromatography (SiO2, heptane/AcOEt) delivered 1.6 g (58%) of the title compound (purity ˜80%) as a yellow foam.

후처리

  1. additionThe reaction mixture was then poured
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness

출처 및 근거

ORD 기록
ord-6bb9377841a14fbfb30269b29c283ebe
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07348349B2

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