Triacetoxyperiodinane → 2-(3-Bromo-quinolin-6-yloxy)-N-(1-cyano-1-methyl-2-oxo-ethyl)-2-methylsulfanyl-acetamide

HRID 1892045ノート

反応式

HRID 1892045 の反応式
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH:13]([S:23][CH3:24])[C:14]([NH:16][C:17]([C:21]#[N:22])([CH3:20])[CH2:18][OH:19])=[O:15])=[CH:7][CH:6]=2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH:13]([S:23][CH3:24])[C:14]([NH:16][C:17]([C:21]#[N:22])([CH3:20])[CH:18]=[O:19])=[O:15])=[CH:7][CH:6]=2

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 667174052-(3-Bromo-quinolin-6-yloxy)-N-(1-cyano-2-hydroxy-1-methyl-ethyl)-2-methylsulfanyl acetamide

生成物 1

HCID 866480222-(3-Bromo-quinolin-6-yloxy)-N-(1-cyano-1-methyl-2-oxo-ethyl)-2-methylsulfanyl-acetamide収率 60.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-(3-Bromo-quinolin-6-yloxy)-N-(1-cyano-2-hydroxy-1-methyl-ethyl)-2-methylsulfanyl acetamide (0.660 g) from Stage 1 above in dichloromethane (25 ml) was treated with Dess-Martin periodinane (0.819 g). The reaction mixture was stirred at R.T. for 2 h 30. The reaction mixture was quenched with sat. aqueous NaHCO3 and sat. aqueous sodium thiosulphate. The reaction mixture was vigorously stirred at rt. for 30 minutes after which time the two phases were separated. The organic layer was washed with sat. aqueous. NaHCO3. After separation the organic phase was dried over sodium sulphate, filtered and evaporated to yield 0.397 g of 2-(3-Bromo-quinolin-6-yloxy)-N-(1-cyano-1-methyl-2-oxo-ethyl)-2-methylsulfanyl-acetamide as a crude product which was used in the next step without any further purification.

後処理

  1. customThe reaction mixture was quenched with sat. aqueous NaHCO3 and sat. aqueous sodium thiosulphate
  2. stirringThe reaction mixture was vigorously stirred at rt
  3. customfor 30 minutes after which time the two phases were separated
  4. washThe organic layer was washed with sat. aqueous
  5. customAfter separation the organic phase
  6. dry with materialwas dried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-9838cc6573304717b6078f38237e6ea5
出典データセット
uspto-grants-2013_08
特許番号
US08507509B2

反応ノート

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