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Sodium Thiosulfate → 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-methyl-2-oxo-1-prop-2-ynyloxymethyl-ethyl)-2-methylsulfanyl acetamide

HRID 1962877
ノート
印刷プレビュー

反応式

HRID 1962877 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:27][CH3:28])[C:15]([NH:17][C:18]([CH3:26])([CH2:21][O:22][CH2:23][C:24]#[CH:25])[CH2:19][OH: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:27][CH3:28])[C:15]([NH:17][C:18]([CH3:26])([CH2:21][O:22][CH2:23][C:24]#[CH:25])[CH:19]=[O:20])=[O:16])=[CH:8][CH:7]=2)#[CH:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 595654102-(3-ethynyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methyl-1-prop-2-ynyloxymethyl-ethyl)-2-methylsulfanyl-acetamide

生成物 1

HCID 595653162-(3-ethynyl-quinolin-6-yloxy)-N-(1-methyl-2-oxo-1-prop-2-ynyloxymethyl-ethyl)-2-methylsulfanyl acetamide収率 110.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-(3-Ethynyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methyl-1-prop-2-ynyloxymethyl-ethyl)-2-methylsulfanyl-acetamide (1.0 g) from Stage 3 above in dichloromethane (40 ml) was treated with Dess-Martin periodinane (1.277 g). The reaction mixture was stirred at room temperature for 2.5 and then treated with sat. aqueous NaHCO3 and sat. aqueous sodium thiosulphate. The organic layer was washed with sat. aqueous NaHCO3. After separation, the organic phase was dried over sodium sulphate, filtered and evaporated to yield 1.10 g of 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-methyl-2-oxo-1-prop-2-ynyloxymethyl-ethyl)-2-methylsulfanyl acetamide as a crude product which was used in the next step (Stage 5, described below) without any further purification. 1H NMR (CDCl3) δ ppm: [{9.51 (s), 9.49 (s) 1H}, isomer A and isomer B]; 8.86 (1H, d); 8.22 (1H, d); 8.07 (1H, d); 7.53-7.50 (1H, m); [{7.58 (s br), 7.48 (s br) 1H}, isomer A and isomer B]; 7.26 (1H, m); 5.72 (1H, s); 4.16-3.87 (4H, m); 3.28 (1H, s); 2.48 (1H, m); [{2.22 (s), 2.20 (s) 3H}, isomer A and isomer B]; 1.52 (3H, s).

後処理

  1. washThe organic layer was washed with sat. aqueous NaHCO3
  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-7e5b5a1853574ee7b8eda6648cba9a0b
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08415272B2

反応ノート

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