Water → HCID 14208923, compound

HRID 1534850Notes

Reaction equation

HRID 1534850 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2/[CH:18]=[C:19](/[C:21]([OH:23])=[O:22])\[CH3:20])[C:10]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:9]([CH3:29])[NH:8][C:7]=1[CH3:30])=[O:5])[CH3:2].[CH2:31](Br)[CH3:32].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2/[CH:18]=[C:19](\[CH3:20])/[C:21]([O:23][CH2:31][CH3:32])=[O:22])[C:10]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:9]([CH3:29])[NH:8][C:7]=1[CH3:30])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 67904952HCID 67904952, compound

Product 1

HCID 14208923HCID 14208923, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of Compound A (4 g), ethyl bromide (1 g) and potassium carbonate (30 g) in dimethylformamide (60 ml) was stirred at room temperature for 6 h. The mixture was poured into water and extracted with ethyl acetate, then washed thoroughly with water and dried over Na2SO4. Evaporation of the solvent gave an oil which was triturated with petrol and recrystallized from petrol ether to give the title compound as a white solid (3.2 g). M.p. 105°-106°.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed thoroughly with water
  3. dry with materialdried over Na2SO4
  4. customEvaporation of the solvent
  5. customgave an oil which
  6. customwas triturated with petrol
  7. customrecrystallized from petrol ether

Sources & evidence

ORD record
ord-8d6b883071b144c9a238df959d85529d
Source dataset
uspto-grants-1992_02
Patent number
US05091395

Reaction notes

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