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

HRID 1892049
ノート
印刷プレビュー

反応式

HRID 1892049 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>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

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 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 R.T. for 2 h 30 and then, 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 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 (along with minor impurities. The crude mixture was used in the next step without any further purification.

後処理

  1. customquenched 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
  6. dry with materialthe organic phase was dried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-ae8c44698f894ef58e090db17273c0e1
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08507509B2

反応ノート

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