Triethylamine → HCID 86648423, compound

HRID 2387410Notes

Reaction equation

HRID 2387410 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH3:26])[O:10][CH2:9][CH:8]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][N:16]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)[CH3:18])[CH2:7][O:6]1)=[O:4].C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>ClCCl>[CH3:1][O:2][C:3]([C:5]1([CH3:26])[O:10][CH2:9][CH:8]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][N:16]=[C:17]([C:19]2[CH:20]=[CH:21][C:22]([O:25][S:35]([CH3:34])(=[O:37])=[O:36])=[CH:23][CH:24]=2)[CH3:18])[CH2:7][O:6]1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 136397323HCID 136397323, compound

Product 1

HCID 86648423HCID 86648423, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice cold solution of Methyl-5-{4-[1-(4-hydroxy-phenyl)-ethylideneaminooxy]-butyl}-2-methyl-[1,3]dioxane-2-carboxylate (prepared as per example 40) (200 mg) in anhydrous dichloromethane were added triethyl amine (82 mg) and methane sulfonyl chloride (75 mg) and the reaction mixture was stirred at the same temperature for about an hour. Reaction mixture was diluted with dichloromethane, washed with water, dried over sodium sulphate and evaporated under, reduced pressure on a rotavapor. Crude product was flash chromatographed over silica gel using 20% ethyl acetate in petroleum ether as eluent to obtain 200 mg of pure product.

Workup

  1. customReaction mixture
  2. washwashed with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated under, reduced pressure on a rotavapor
  5. customchromatographed over silica gel using 20% ethyl acetate in petroleum ether as eluent

Sources & evidence

ORD record
ord-b61a56a63724466688df5eb7fb0f5741
Source dataset
uspto-grants-2012_09
Patent number
US08268867B2

Reaction notes

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