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

HRID 1892056ノート

反応式

HRID 1892056 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]1([CH2:22][OH:23])[CH2:21][CH2:20][CH2:19]1)=[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+]>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:24][CH3:25])[C:15]([NH:17][C:18]1([CH:22]=[O:23])[CH2:21][CH2:20][CH2:19]1)=[O:16])=[CH:8][CH:7]=2)#[CH:2]

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

To a solution of 2-(3-Ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-cyclobutyl)-2-methylsulfanyl-acetamide (310 mg) in CH2Cl2 (30 ml) was added solid Dess Martin periodinane (480 mg) at room temperature, under nitrogen atmosphere. The mixture was stirred at the same temperature during 1 hour, then poured into sat aq NaHCO3 and extracted with CH2Cl2 (2×15 ml). The organic phase was separated and washed with aq Na2S2O3 and sat. aq. NaCl then dried over anhydrous sodium sulphate, filtered and evaporated under vacuum. The crude compound (250 mg) as yellow oil, was used for the next step without purification.

後処理

  1. additionpoured
  2. extractionextracted with CH2Cl2 (2×15 ml)
  3. customThe organic phase was separated
  4. washwashed with aq Na2S2O3 and sat. aq. NaCl
  5. dry with materialthen dried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. customThe crude compound (250 mg) as yellow oil, was used for the next step without purification

出典と根拠

ORDレコード
ord-c00f19984438428d9134a96813e2bf23
出典データセット
uspto-grants-2013_08
特許番号
US08507509B2

反応ノート

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