Toluene → HCID 178448140、化合物

HRID 1694888ノート

反応式

HRID 1694888 の反応式
N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1.O[CH2:21][C@H:22]([NH:32][S:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[N+:42]([O-:44])=[O:43])(=[O:35])=[O:34])[C@@H:23]1[CH2:27][C@@H:26]([CH:28]([CH3:30])[CH3:29])[C:25](=[O:31])[O:24]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH:28]([C@@H:26]1[CH2:27][C@@H:23]([CH:22]2[CH2:21][N@@:32]2[S:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[N+:42]([O-:44])=[O:43])(=[O:35])=[O:34])[O:24][C:25]1=[O:31])([CH3:30])[CH3:29]

参加物

6

反応物 4

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 54578740N-{(S)-2-hydroxy-1-[(2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamide

生成物 1

HCID 178448140HCID 178448140、化合物収率 89.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

5.9 ml of a solution of diethyl azodicarboxylate in toluene (40%) (12.9 mmol) was added to a solution of 4.00 g of N-{(S)-2-hydroxy-1-[(2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamide obtained in Example (1f) (10.7 mmol) and 3.38 g of triphenylphosphine (12.9 mmol) in tetrahydrofuran (100 ml) under ice-cooling over 10 minutes, and the mixture was stirred at the same temperature for 10 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: toluene/acetone=5/1) to obtain 3.40 g of the title compound (yield: 89%).

後処理

  1. temperaturecooling over 10 minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (elution solvent: toluene/acetone=5/1)

出典と根拠

ORDレコード
ord-d0ba49a87dab436ea5f45d0c49541fbc
出典データセット
uspto-grants-2012_04
特許番号
US08158790B2

反応ノート

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