Triacetoxyperiodinane → 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-formyl-cyclobutyl)-2-methylsulfanyl-acetamide

HRID 1962887ノート

反応式

HRID 1962887 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([C:25]1[CH:26]=[N:27][C:28]2[C:33]([CH:34]=1)=[CH:32][C:31]([O:35][CH:36]([S:46][CH3:47])[C:37]([NH:39][C:40]1([CH2:44][OH:45])[CH2:43][CH2:42][CH2:41]1)=[O:38])=[CH:30][CH:29]=2)#[CH:24].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:23]([C:25]1[CH:26]=[N:27][C:28]2[C:33]([CH:34]=1)=[CH:32][C:31]([O:35][CH:36]([S:46][CH3:47])[C:37]([NH:39][C:40]1([CH:44]=[O:45])[CH2:43][CH2:42][CH2:41]1)=[O:38])=[CH:30][CH:29]=2)#[CH:24]

参加物

5

反応物 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 595653282-(3-ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-cyclobutyl)-2-methylsulfanyl-acetamide

生成物 1

HCID 595654712-(3-ethynyl-quinolin-6-yloxy)-N-(1-formyl-cyclobutyl)-2-methylsulfanyl-acetamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Dess-Martin periodinane (424 mg) was added to a solution of 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-cyclobutyl)-2-methylsulfanyl-acetamide (360 mg) in CH2Cl2, at room temperature, under nitrogen atmosphere. The yellow mixture was stirred during 1 hr, then poured into aq NaHCO3 soln and extracted with CH2Cl2. The combined organic layers were washed with aqueous thiosulphate solution, brine, dried over sodium sulphate anhydrous, filtered and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 1/1) to give 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-formyl-cyclobutyl)-2-methylsulfanyl-(260 mg) as slightly green oil which was used as such in the following step.

後処理

  1. extractionextracted with CH2Cl2
  2. washThe combined organic layers were washed with aqueous thiosulphate solution, brine
  3. dry with materialdried over sodium sulphate anhydrous
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 1/1)
  7. customto give 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-formyl-cyclobutyl)-2-methylsulfanyl-(260 mg) as slightly green oil which

出典と根拠

ORDレコード
ord-2645c51910c74297aae0beeeb611a7cd
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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