Sodium Thiosulfate → HCID 59565387、化合物

HRID 1962872ノート

反応式

HRID 1962872 の反応式
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:24][CH3:25])[C:15]([NH:17][C:18]([CH2:22][OH:23])([CH3:21])[C:19]#[CH:20])=[O:16])=[CH:8][CH:7]=2)#[CH:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:24][CH3:25])[C:15]([NH:17][C:18]([CH:22]=[O:23])([CH3:21])[C:19]#[CH:20])=[O:16])=[CH:8][CH:7]=2)#[CH:2]

参加物

6

反応物 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 595653502-(3-ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-1-methylprop-2-ynyl)-2-methylsulfanyl acetamide

生成物 1

HCID 59565387HCID 59565387、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-(3-Ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-1-methylprop-2-ynyl)-2-methylsulfanyl acetamide (0.513 g) in dichloromethane (25 ml) was treated with Dess-Martin periodinane (0.737 g). The reaction mixture was stirred at 0.646 g for 2 hrs and then treated with sat. aqueous NaHCO3 and sat. aqueous sodium thiosulphate. The organic layer was washed thrice with sat. aqueous. NaHCO3. After separation, the organic phase was dried over sodium sulphate, filtered and evaporated to yield crude 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-formyl-1-methyl-prop-2-ynyl)-2-methylsulfanyl acetamide which was used as such in Stage 6. 1H NMR (CDCl3) δ ppm: 9.40 (1H, s); 8.86 (1H, d); 8.22 (1H, d); 8.07 (1H, d); 7.52-7.49 (1H, m); [{7.49 (s br), 7.44 (s br) 1H}, isomer A and isomer B]; 7.26 (1H, m); [{5.74 (s), 5.72 (s) 1H}, isomer A and isomer B]; 3.29 (1H, s); 2.54 (1H, s); [{2.23 (s), 2.21 (s) 3H}, isomer A and isomer B]; 1.79 (3H, s).

後処理

  1. washThe organic layer was washed thrice with sat. aqueous
  2. customAfter separation
  3. dry with materialthe organic phase was dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated

出典と根拠

ORDレコード
ord-0f0a1b711952461c93394a0aea56333a
出典データセット
uspto-grants-2013_04
特許番号
US08415272B2

反応ノート

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