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

HRID 1962861

Reaction equation

HRID 1962861 reaction equation
[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][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: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]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 595653712-(3-Ethynyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamide

Product 1

HCID 59565278(3-Ethynyl-quinolin-6-yloxy)-N-(1-methoxymethyl-1-methyl-2-oxo-ethyl)-2-methylsulfanyl-acetamideYield 60.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(3-Ethynyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamide (200 mg) in dry CH2Cl2 (15 ml) was treated with Dess-Martin periodinane (295 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 (120 mg) as yellowish oil as a mixture of diastereoisomers.

Workup

  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)

Sources & evidence

ORD record
ord-d725e15165c049f390a39b5233ffff83
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Linked notes

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