Triacetoxyperiodinane → 2-chloro-N-(4-(((2-oxo-1-phenylpropyl)amino)carbonyl)phenyl)benzamide

HRID 1951583ノート

反応式

HRID 1951583 の反応式
[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([NH:15][CH:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]([OH:19])[CH3:18])=[O:14])=[CH:9][CH:8]=1)=[O:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]([NH:15][CH:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17](=[O:19])[CH3:18])=[O:14])=[CH:11][CH:12]=1)=[O:5]

参加物

5

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 574653742-chloro-N-(4-(((2-hydroxy-1-phenylpropyl)amino)carbonyl)phenyl)benzamide

生成物 1

HCID 574653752-chloro-N-(4-(((2-oxo-1-phenylpropyl)amino)carbonyl)phenyl)benzamide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

a mixture of 2-chloro-N-(4-(((2-hydroxy-1-phenylpropyl)amino) carbonyl)phenyl)benzamide (294 mg, 719 μmol) and Dess-Martin periodinane (335 mg, 791 μmol) in 5 mL dichloromethane+1 mL DMF was stirred at room temperature for 2 hours then diluted with 20 mL ethyl acetate and washed with 10 mL each water and brine. The organic layer was stirred over magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to afford a yellow solid. The solid was slurried in hot ethyl acetate and left to equilibrate to room temperature. After 48 h, the solid was collected by filtration, rinsing with ethyl acetate and drying over a stream of air (200 mg, 68%). ESI+ m/z=407.0 [MH]+.

後処理

  1. washwashed with 10 mL each water and brine
  2. stirringThe organic layer was stirred over magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customto afford a yellow solid
  6. waitleft
  7. customto equilibrate to room temperature
  8. waitAfter 48 h
  9. filtrationthe solid was collected by filtration
  10. washrinsing with ethyl acetate
  11. customdrying over a stream of air (200 mg, 68%)

出典と根拠

ORDレコード
ord-dc2335b733584077b042e98bee9257cf
出典データセット
uspto-grants-2013_03
特許番号
US08404722B2

反応ノート

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