Benzyl Alcohol → HCID 21054729、化合物

HRID 970373ノート

反応式

HRID 970373 の反応式
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][C:28]([C:34]([F:37])([F:36])[F:35])(C(O)=O)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].CCN(CC)CC.[CH2:45]([OH:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.[N-:53]=[C:54]=[O:55]>C1(C)C=CC=CC=1>[CH2:45]([O:52][C:54]([NH:53][C:28]1([C:34]([F:35])([F:36])[F:37])[CH2:27][CH2:26][N:25]([C:23]([O:22][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:24])[CH2:30][CH2:29]1)=[O:55])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

参加物

7

反応物 5

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 105034IsocyanateHCID 199401P,P-Diphenylphosphinic azideHCID 179831391-(tert-Butoxycarbonyl)-4-(trifluoromethyl)piperidine-4-carboxylic acid

生成物 1

HCID 21054729HCID 21054729、化合物

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

Diphenylphosphoryl azide (1.1 equiv.) is added to a solution of 1-(tert-butoxycarbonyl)-4-(trifluoromethyl)piperidine-4-carboxylic acid (3c) (1 equiv.) and Et3N (1 equiv.) in dry toluene at room temperature, and the reaction is warmed gradually to 80° C. The reaction is kept at 80° C. until gas evolution stops, then dry benzyl alcohol (2 equiv.) is added. The reaction is stirred at 80° C. until the isocyanate is consumed, then the solvents are removed in vacuo. The residue is taken up in CH2Cl2 and the solution is washed sequentially with dilute HCl, dilute NaOH, and H2O. The solution is dried (MgSO4) and concentrated in vacuo, and the residue is purified by flash chromatography on silica gel to afford the title compound.

後処理

  1. customis kept at 80° C. until gas evolution
  2. customis consumed
  3. customthe solvents are removed in vacuo
  4. washthe solution is washed sequentially with dilute HCl, dilute NaOH, and H2O
  5. dry with materialThe solution is dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customthe residue is purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-a4e448ee4cc9426aa230e512d5b0561e
出典データセット
uspto-grants-2007_12
特許番号
US07312212B2

反応ノート

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