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

HRID 1962887Notes

Reaction equation

HRID 1962887 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2645c51910c74297aae0beeeb611a7cd
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

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