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

HRID 1892056노트

반응식

HRID 1892056 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c00f19984438428d9134a96813e2bf23
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507509B2

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