Ethyl Bromide → HCID 14547437, compound

HRID 1032369Notes

Reaction equation

HRID 1032369 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][C:23]#[C:24][C:25]([OH:27])=[O:26])=[C:10]1[C:28]([O:30][CH2:31][CH3:32])=[O:29].[OH-].[CH2:34]([N+](C)(C)C)[C:35]1C=CC=CC=1.C(Br)C>CS(C)=O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][C:23]#[C:24][C:25]([O:27][CH2:34][CH3:35])=[O:26])=[C:10]1[C:28]([O:30][CH2:31][CH3:32])=[O:29]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 66854Benzyltrimethylammonium hydroxideHCID 22165626HCID 22165626, compound

Product 1

HCID 14547437HCID 14547437, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}-2-butynoic acid (2.50 g), benzyltrimethylammonium hydroxide (0.87 g) and ethyl bromide (0.62 g) in dimethyl sulphoxide (5 ml) was stirred at room temperature for 48 hours, quenched into water and extracted twice into ethyl acetate. The combined ethyl acetate extracts were washed with water, dried over MgSO4 and evaporated. The residue was crystallised from methanol to give the title compound (2.22 g), m.p. 123°-125°.

Workup

  1. customquenched into water
  2. extractionextracted twice into ethyl acetate
  3. washThe combined ethyl acetate extracts were washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was crystallised from methanol

Sources & evidence

ORD record
ord-ebd52f2847054a9c9a1feead079515f2
Source dataset
uspto-grants-1990_09
Patent number
US04957930

Reaction notes

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