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Acetic Anhydride → N-[(5S)-3-(4-(4-t-Butyldimethylsilyloxymethylimidazol-1-yl)-3-fluorophenyl)-2-oxooxazolidin-5-ylmethyl]acetamide

HRID 636707
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HRID 636707 반응식
[N:1]([CH2:4][C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:21]=[C:20]([CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[N:19]=[CH:18]3)=[C:13]([F:31])[CH:12]=2)[CH2:6]1)=[N+]=[N-].C(N(CC)CC)C.[C:39](OC(=O)C)(=[O:41])[CH3:40]>C(OCC)(=O)C.[Pd]>[Si:24]([O:23][CH2:22][C:20]1[N:19]=[CH:18][N:17]([C:14]2[CH:15]=[CH:16][C:11]([N:7]3[CH2:6][C@H:5]([CH2:4][NH:1][C:39](=[O:41])[CH3:40])[O:9][C:8]3=[O:10])=[CH:12][C:13]=2[F:31])[CH:21]=1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 57114338(5R)-5-Azidomethyl-3-(4-(4-t-butyldimethylsilyloxymethylimidazol-1-yl)-3-fluorophenyl)-oxazolidin-2-one

생성물 1

HCID 10695375N-[(5S)-3-(4-(4-t-Butyldimethylsilyloxymethylimidazol-1-yl)-3-fluorophenyl)-2-oxooxazolidin-5-ylmethyl]acetamide

시약·촉매·용매 2

HCID 23938Palladium
촉매
HCID 8857Ethyl Acetate용매

실험 절차

To (5R)-5-azidomethyl-3-(4-(4-t-butyldimethylsilyloxymethylimidazol-1-yl)-3-fluorophenyl)oxazolidin-2-one(10.0 g) in ethyl acetate (560 ml) was added triethylamine (13.3 ml), acetic anhydride (4.5 ml), and palladium catalyst (10% on charcoal, 1.5 g), and the mixture hydrogenated at ambient temperature for 17 hours. The mixture was filtered through celite, the celite washed well with ethyl acetate, and the organic layer stirred with a saturated solution of sodium bicarbonate (100 ml) at ambient temperature for 1 hour. The organic layer was separated, dried over magnesium sulfate, and evaporated. Crude product (15 g, from two batches) was dissolved in dichloromethane and chromatographed on silica, eluting with a gradient from dichloromethane (100%) to 10% methanol in dichloromethane. Product fractions were combined to give a gum (12.3 g).

후처리

  1. filtrationThe mixture was filtered through celite
  2. washthe celite washed well with ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. dissolutionCrude product (15 g, from two batches) was dissolved in dichloromethane
  7. customchromatographed on silica
  8. washeluting with a gradient from dichloromethane (100%) to 10% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-3143a3c396364f97a4c1d2dfd5c32f0e
출처 데이터셋
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06194441B1

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