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

HRID 1962864ノート

反応式

HRID 1962864 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:25][CH3:26])[C:15]([NH:17][C:18]([CH2:22][O:23][CH3:24])([CH3:21])[CH2:19][OH:20])=[O:16])=[CH:8][C:7]=2C)#[CH:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[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:25][CH3:26])[C:15]([NH:17][C:18]([CH2:22][O:23][CH3:24])([CH3:21])[CH:19]=[O:20])=[O:16])=[CH:8][CH:7]=2)#[CH:2]

参加物

5

反応物 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 595653242-(3-ethynyl-8-methyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamide

生成物 1

HCID 59565278(3-Ethynyl-quinolin-6-yloxy)-N-(1-methoxymethyl-1-methyl-2-oxo-ethyl)-2-methylsulfanyl-acetamide収率 93.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 2-(3-ethynyl-8-methyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamide (240 mg) in dry CH2Cl2 (15 ml) was treated with Dess-Martin periodinane (341 mg). The mixture was stirred at room temperature during 1 h then poured on sat aq NaHCO3. After separation the water phase was washed twice with CH2Cl2 The combined organic phases were washed with brine, dried over sodium sulfate, filtered and evaporated. The crude residue was purified by column chromatography (cyclohexane/ethyl acetate 1:1) to give (3-ethynyl-quinolin-6-yloxy)-N-(1-methoxymethyl-1-methyl-2-oxo-ethyl)-2-methylsulfanyl-acetamide (215 mg) as yellowish oil as a mixture of diastereoisomers.

後処理

  1. additionthen poured
  2. customAfter separation the water phase
  3. washwas washed twice with CH2Cl2 The combined organic phases
  4. washwere washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude residue was purified by column chromatography (cyclohexane/ethyl acetate 1:1)

出典と根拠

ORDレコード
ord-b7564a577d79463aa1ecbd5a543cc8c2
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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