Acetic Anhydride → (S)-N-[[3-(3-Fluorophenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 2256415

反応式

HRID 2256415 の反応式
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][C@H:11]([CH2:13][N:14]=[N+]=[N-])[O:10][C:9]2=[O:17])[CH:5]=[CH:6][CH:7]=1.[H][H].[N-]=[N+]=[N-].[C:23](OC(=O)C)(=[O:25])[CH3:24]>C(OCC)(=O)C.[Pd].CO.C(Cl)(Cl)Cl.N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][C@H:11]([CH2:13][NH:14][C:23](=[O:25])[CH3:24])[O:10][C:9]2=[O:17])[CH:5]=[CH:6][CH:7]=1

参加物

9

反応物 4

HCID 7918Acetic AnhydrideHCID 33558AzideHCID 11550435(5R)-5-(Azidomethyl)-3-(3-fluorophenyl)-2-oxazolidinoneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 11345751(S)-N-[[3-(3-Fluorophenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒HCID 21584188Chloroform methanol溶媒

実験手順

A mixture of (R)-[3-(3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl azide (PREPARATION 16, 8.200 g, 34.71 mol) in ethyl acetate (100 ml) is treated with palladium on carbon (10%, 0.820 g) under nitrogen. The atmosphere is then replaced with hydrogen (balloon) via repeated evacuation and filing. After stirring under hydrogen for 17 hr, TLC in methanol/chloroform (5/95) reveals the azide starting material is cushioned. The atmosphere is replaced with nitrogen and then pyridine (6 ml) and acetic anhydride (4.1 ml, 43.40 mmol) are added to the reaction mixture. The reaction mixture is stirred for 1 hr at 20°-25° and then filtered through Celite, washing the pad with ethyl acetate. The filtrate is concentrated under reduced pressure and the residue taken-up in dichloromethane. The addition of ether affords a precipitate. After standing in the refrigerator overnight the solids are collected by vacuum filtration, washed with cold hexane, and dried under reduced pressure to give the title compound as a solid. The crude product is purified by chromatography over silica gel, eluting with methanol/chloroform (5/95). The appropriate fractions are pooled and concentrated to give the title compound, mp 140.0°-140.5°; [α]25D -6.6° (c 1.0, CHCl3).

後処理

  1. stirringThe reaction mixture is stirred for 1 hr at 20°-25°
  2. filtrationfiltered through Celite
  3. washwashing the pad with ethyl acetate
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. additionThe addition of ether
  6. customaffords a precipitate
  7. customAfter standing in the refrigerator overnight
  8. filtrationare collected by vacuum filtration
  9. washwashed with cold hexane
  10. customdried under reduced pressure

出典と根拠

ORDレコード
ord-c8f1772d8b5a4b3a8dc271fd31b7b89f
出典データセット
uspto-grants-1997_08
特許番号
US05654435

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