Propionyl chloride → HCID 44211248, compound

HRID 52053

Reaction equation

HRID 52053 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[N:6]1([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]([O:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][NH:24][C:25](=[O:31])[CH2:26][S:27][CH2:28][CH2:29][OH:30])[CH:14]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[N:6]1([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]([O:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][NH:24][C:25](=[O:31])[CH2:26][S:27][CH2:28][CH2:29][O:30][C:1](=[O:4])[CH2:2][CH3:3])[CH:14]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 516892Sodium BicarbonateHCID 67725880N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-hydroxyethylthio)acetamide

Product 1

HCID 44211248HCID 44211248, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.09 ml of propionyl chloride was added to a mixture of 0.40 g of N-[4-(4-piperidinomethyl-2-pyridyloxy) -cis-2-butenyl]-2-(2-hydroxyethylthio)acetamide (prepared as described in Example 1) and 1.02 ml of pyridine, and the resulting mixture was allowed to stand at room temperature for 2 hours. At the end of this time, the reaction mixture was poured into ice-water, and a saturated aqueous solution of sodium hydrogencarbonate was added to the resulting mixture, after which it was extracted with chloroform. The extract was concentrated by evaporation under reduced pressure and the residue was purified by column chromatography through silica gel, using a 1:19 by volume mixture of methanol and ethyl acetate as the eluent, to give 0.39 g (yield 85%) of the title compound as an oil.

Workup

  1. extractionafter which it was extracted with chloroform
  2. concentrationThe extract was concentrated by evaporation under reduced pressure
  3. customthe residue was purified by column chromatography through silica gel
  4. additionby volume mixture of methanol and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-0d44a03b9b0e4691a156f7a6265534b7
Source dataset
uspto-grants-1997_04
Patent number
US05616579

Linked notes

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