Triacetoxyperiodinane → N-Cyclopropyl-4-methyl-3-[3-[[(1R,2R)-2-methyl-3-oxo-1-phenylpropyl]amino]-2-oxo-1(2H)-pyrazinyl]-benzamide

HRID 337052ノート

反応式

HRID 337052 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH:23]1([NH:26][C:27](=[O:54])[C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([N:35]3[CH:40]=[CH:39][N:38]=[C:37]([NH:41][C@@H:42]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[C@@H:43]([CH3:46])[CH2:44][OH:45])[C:36]3=[O:53])[CH:29]=2)[CH2:25][CH2:24]1>ClCCl>[CH:23]1([NH:26][C:27](=[O:54])[C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([N:35]3[CH:40]=[CH:39][N:38]=[C:37]([NH:41][C@@H:42]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[C@@H:43]([CH3:46])[CH:44]=[O:45])[C:36]3=[O:53])[CH:29]=2)[CH2:24][CH2:25]1

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 66685987N-Cyclopropyl-3-[3-[[(1R,2R)-3-hydroxy-2-methyl-1-phenylpropyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzamide

生成物 1

HCID 86663242N-Cyclopropyl-4-methyl-3-[3-[[(1R,2R)-2-methyl-3-oxo-1-phenylpropyl]amino]-2-oxo-1(2H)-pyrazinyl]-benzamide収率 117.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
25 °C

実験手順

A solution of Dess-Martin periodinane (600 mg) in dichloromethane (3 mL) was added dropwise to a solution of N-cyclopropyl-3-(3-((1R,2R)-3-hydroxy-2-methyl-1-phenylpropylamino)-2-oxopyrazin-1(2H)-yl)-4-methylbenzamide (Example 136, 405 mg) in dichloromethane (4 mL) at 25° C. The resulting mixture was stirred at 25° C. for 30 minutes. The reaction mixture was quenched with sat. aqueous Na2S2O3 (7 mL) and sat. aqueous NaHCO3. The mixture was stirred for 15 min. and extracted into dichloromethane. The organic phase was dried (Na2SO4), filtered and evaporated to afford crude product (475 mg) that was used in the next step without purification.

後処理

  1. customThe reaction mixture was quenched with sat. aqueous Na2S2O3 (7 mL) and sat. aqueous NaHCO3
  2. stirringThe mixture was stirred for 15 min.
  3. extractionextracted into dichloromethane
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-bfa782437b1941fda458227b85761732
出典データセット
uspto-grants-2014_11
特許番号
US08889692B2

反応ノート

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