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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
ノート
印刷プレビュー

反応式

HRID 1394749 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6422
Trifluoroacetic acid
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6bb9377841a14fbfb30269b29c283ebe
出典データセット
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07348349B2

反応ノート

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